Experience excitement as you journey through Chicago Scavenger Hunt,Magnificent Mile Scavenger Hunt,Chicago Ghost Tour,Chicago Bar Crawl,Lincoln Park Zoo Scavenger Hunt,and more—each adventure reveals city icons and off-the-beaten-path wonders.
Challenge your friends with trivia quests or bold photo dares using our app; earn points as you go and celebrate together at the finish line!
Top Outdoor Activities In Chicago, Illinois
Step into the heart of Chicago, where the city's energy pulses from Millennium Park to the vibrant streets of The Loop. Outdoor activities in Chicago invite you to see iconic landmarks and hidden corners like never before. Whether you are a visitor or a local, these experiences offer fresh ways to view Chicago, spark laughter, and create memories. Get ready for adventures that make every moment unforgettable.
Outdoor Experiences in Chicago, Illinois
Our expertly curated list of outdoor activities in Chicago is designed for thrill-seekers and explorers alike. Each experience blends creativity, teamwork, and discovery for an adventure unlike any other in the Windy City. You will uncover must-see attractions, quirky art galleries, buzzing live music scenes, and even craft beer gems—all while having fun outdoors. Dive in below and discover new ways to enjoy sightseeing and top experiences around Chicago.
Top Rated
4.8 (938 reviews)
Time For A GO in Chicago Around The Chicago Bean Scavenger Hunt
Chicago Loop, Chicago
Get ready to explore the vibrant streets of Chicago Loop on a thrilling scavenger hunt!...
4.9 (257 reviews)
Chicago's Magnificent Mile Scavenger Hunt
Magnificent Mile, Chicago
Discover the hidden history and incredible sites of Chicago's Magnificent Mile, one of...
4.9 (239 reviews)
Ghosts of the Chicago River Ghost Tour
Downtown Ghost Tour, Chicago
Chicago's ghoulish sites are not for the faint of heart.
4.9 (12 reviews)
Lincoln Park Zoo-per Scavenger Hunt
Lincoln Park Zoo, Chicago
In Chicago, we don’t lion about our love for exploration! Join our two-mile scavenger...
5.0 (18 reviews)
Gold Coast Treasure Hunt Scavenger Hunt
Gold Coast, Chicago
Gold Coast galore! Join our thrilling scavenger hunt to uncover Chicago’s most...
5.0 (15 reviews)
Pilsen Prowl n‘ Plunder Hunt
Pilsen Neighborhood Art Walk, Chicago
Tracking down the some of the most captivating street-art in Chicago
4.9 (15 reviews)
Chi-Town Showdown
Downtown Bar Crawl, Chicago
It's battle royale through the bars of Chicago as players race through crazy challenges...
5.0 (14 reviews)
Pubs and Cubs in Wrigleyville! Scavenger Hunt
Wrigleyville, Chicago
Explore the Windy City's colorful neighborhood on a thrilling scavenger hunt. Uncover...
5.0 (17 reviews)
Wicker Park Scavenger Hunt Scavenger Hunt
Wicker Park, Chicago
Join us on a hilarious adventure through West Town in Chicago! Discover hidden gems and...
5.0 (16 reviews)
Windy City Wonders Chicago Audio Tour Adventure
Downtown Audio Tour, Chicago
Discover the Windy City's hidden treasures on an exciting self-guided audio tour. Uncover...
4.9 (16 reviews)
Andersonville Scavenger Hunt Scavenger Hunt
Andersonville, Chicago
Windy City, more like Findy City! Join our thrilling scavenger hunt in Edgewater Glen for...
5.0 (15 reviews)
Garfield's Parkside Pursuit Scavenger Hunt
Garfield Park, Chicago
Windy City‘s secret treasures await in our Garfield Park scavenger hunt! Discover...
4.8 (14 reviews)
Hyde Park Scavenger Hunt Scavenger Hunt
Chicago Hyde Park, Chicago
Art, nature, and a few surprises await on this fabulous scavenger hunt for U of C...
5.0 (17 reviews)
Groveland Park Chicago scavenger hunt
Groveland Park, Chicago
Windy City? More like findy city! Join our scavenger hunt through Groveland Park‘s...
5.0 (13 reviews)
Home Alone: The McCallister Map Run Scavenger Hunt
Downtown, Chicago
Outsmart boredom, ya filthy animals! Tour Home Alone’s Winnetka: from the McCallister...
5.0 (22 reviews)
DePaul University Hunt
DePaul University, Chicago
Experience a self-guided DePaul University tour with an app-led scavenger hunt featuring...
5.0 (24 reviews)
Order vs. Chaos: The Dark Knight Hunt Scavenger Hunt
Downtown, Chicago
Gotham calls! Hunt Chicago’s Dark Knight sites—from the Old Post Office to Trump...
5.0 (21 reviews)
Ferris Bueller’s Day-Quest Scavenger Hunt
Downtown, Chicago
Take a Ferris-style day off in Chicago: Parking Garage, Daley Plaza, Board of Trade,...
5.0 (25 reviews)
From Meadows to Monuments: Jackson Park Scavenger Hunt Scavenger Hunt
Downtown, Chicago
Get swept away in a scavenger hunt through Chicago’s serene Jackson Park—where...
5.0 (15 reviews)
University of Chicago Hunt
University of Chicago, Chicago
Experience a self-guided University of Chicago tour with an app-led scavenger hunt...
5.0 (25 reviews)
Illinois Institute of Technology Hunt
Illinois Institute of Technology, Chicago
Experience an interactive Illinois Institute of Technology tour with a self-guided,...
5.0 (21 reviews)
Loyola University Chicago Hunt
Loyola University Chicago, Chicago
Experience a self-guided Loyola University Chicago tour with an app-led scavenger hunt...
5.0 (13 reviews)
Chicago Fire: 51-Alarm City Quest Scavenger Hunt
Downtown, Chicago
Answer the call in Chicago! Race from Firehouse 51 to Molly’s Pub, Gaffney, Cinespace,...
5.0 (14 reviews)
Yes, Chef! The Bear’s Chicago Chase Scavenger Hunt
Downtown, Chicago
Suit up for a Chicago kitchen sprint! Hunt flavors and stories from Lou Mitchell’s to...
5.0 (16 reviews)
Family Matters: Riverwalk Riddle Run Scavenger Hunt
Downtown, Chicago
Chicago gets a sitcom glow-up! Track Family Matters spots—Winslow House, Wabash...
An Epic Chicago, Illinois experience
How Our Chicago, Illinois Outdoor Activities Work
Our team researches every destination—from major cities like Chicago to Midwest hotspots—to bring you expertly crafted outdoor activities tailored with quizzes and creative routes.
During each experience your group explores on foot: answer trivia at landmarks such as Willis Tower, snap photos at public installations near Magnificent Mile, solve puzzles by street murals—all tracked through our app so everyone can compare scores after your adventure.
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Top Outdoor Attractions In Chicago
Chicago's top attractions come alive when experienced through our outdoor activities. Stroll along the Magnificent Mile with fresh eyes as you hunt for public art or test your wits at Millennium Park's Cloud Gate. Explore Lincoln Park Zoo's leafy paths or uncover stories on a ghost tour near Navy Pier. From Willis Tower views to lively bar crawls by the Chicago Riverwalk, each activity offers a unique perspective on what makes this city remarkable. Click on each location to see related activities.
1
Chicago Cultural Center
Marvel at the Chicago Cultural Center's grand exterior, crowned by the world’s largest Tiffany glass dome. Locals know to spot the hidden faces in the stonework—will you? Discover this Lakefront Gem on your walking tour adventure.
2
Crown Fountain
Splash into your next mission at Crown Fountain, where digital faces spout water and laughter echoes all summer. Locals love timing photos with the perfect water burst—think you can catch that shot on this Chi-Town treasure hunt?
3
The Art Institute of Chicago
Lions guard the Art Institute’s grand entrance, a nod to Chicago’s artistic muscle. Locals rub their paws for luck! Let this architectural landmark inspire your next challenge in the heart of the Loop.
4
Chicago Stock Exchange Arch
Visit the Chicago Stock Exchange Arch, a testament to architectural ambition. Spot the intricate carvings and see how many faces you can find—a local trivia challenge awaits!
5
The Bowman and the Spearman
The Bowman and the Spearman stand in Congress Plaza Garden, honoring Chicago’s early residents. Local legend says touching their toes brings good luck—try it during your hunt!
6
Wrigley Square
Wrigley Square buzzes with energy, framed by Millennium Monument. Locals picnic here—spot a chess game as you take on your next mission in The Loop.
7
The Bean
The Bean’s mirror finish warps the skyline—locals call it Cloud Gate. After it's 2024 makeover, it shines brighter than ever. Try to spot your team in this shiny landmark photo challenge.
8
DuSable Bridge
At the foot of the Magnificent Mile, DuSable Bridge is a must-see for it's rich history and stunning river views. This iconic landmark marks Chicago's origins, perfect for an urban adventure.
9
Warwick Allerton Hotel
Explore the Warwick Allerton Hotel, a red-brick icon on North Michigan Avenue. As the first high-rise here, it offers historic charm amidst towering neighbors—a unique urban adventure awaits.
10
Chicago Water Tower
The iconic Chicago Water Tower is a resilient gem! It's limestone structure stands as a testament to survival amidst modern marvels. Ideal for photo challenges and peeking into Chi-Town’s history.
11
Holy Name Cathedral
Marvel at Holy Name Cathedral's grand architecture in The Windy City. Spot the infamous bullet hole echoing tales of Al Capone's era—this landmark blends history with Chi-Town's vibrant energy.
12
The Richard H. Driehaus Museum
Immerse yourself in Gilded Age opulence at the Driehaus Museum in Nickerson House. This urban gem offers dazzling art and architecture amidst The Loop's vibrant energy—a glimpse into Chicago's elite past.
13
Woman’s Athletic Club
Discover Woman's Athletic Club, a trailblazer from 1898 in The Loop. This architectural marvel stands as a testament to female empowerment amidst Chi-Town's vibrant urban energy—a historical treasure.
14
Plaza of the Americas
Discover Plaza of the Americas, a vibrant flag tapestry celebrating the Western Hemisphere in Chi-Town's heart. Enjoy exploring The Loop's culture while snapping photos on your urban adventure quest.
15
Wrigley Building
A beacon of The Loop, Wrigley Building dazzles with it's white terra cotta façade and clock tower. This architectural gem stands proudly at Magnificent Mile’s gateway—a snapshot of Chi-Town’s artistry.
16
Tribune Tower
Tribune Tower dazzles with Gothic splendor, filled with history and intrigue—a Chi-Town marvel! Discover it's rich tapestry and enjoy nearby attractions in The Loop on an urban quest in Skyscraper Haven.
17
The James M. Nederlander Theatre
Feel the chill of history at this iconic theatre in the Windy City. Known for it's eerie past, it's a must-see for those intrigued by Chicago's haunted tales and architectural beauty.
18
The S.S. Eastland
Visit the La Salle St. Bridge for a haunting view of Chicago's past. The site of the tragic Eastland disaster, it's a poignant stop for those exploring the city's darker history.
19
Marina City
Marvel at Marina City's iconic towers along the Chicago Riverwalk. Known for urban legends and stunning architecture, it's a must-see for first-time visitors to the Second City.
20
Old Fort Dearborn
Step onto historic grounds near Fannie May to uncover Fort Dearborn's legacy. This landmark is steeped in local lore, offering a glimpse into Chicago's tumultuous past.
21
Billy Goat Tavern
Experience a lighthearted haunt at Billy Goat Tavern, nestled in The Loop. Known for it's quirky charm and ghostly pranks, it's a fun spot to unwind during your city exploration.
22
TAO Chicago
Explore TAO Chicago's intriguing past along the Magnificent Mile. Known for it's dual tragedies, it offers an atmospheric experience rich with local history and mystery.
23
Chicago River & Lake Michigan
Stroll along these iconic waterways where Prohibition-era spirits are said to linger—a captivating part of any outdoor adventure in Chicago.
24
Three Dots and a Dash
Discover a hidden tiki treasure in the Windy City. Three Dots and a Dash offers a tropical escape with it's vibrant cocktails and Polynesian flair, perfect for an outdoor adventure.
25
Mother Hubbard’s
Dive into Chicago's sports scene at Mother Hubbard's. With numerous TVs and lively patrons, it's an ideal spot for outdoor enthusiasts to catch a game while exploring the city's vibrant atmosphere.
26
O'Callaghan's
Step into O'Callaghan's for an authentic Irish pub experience in Chicago. Enjoy cold brews and friendly faces as you explore this charming part of the city.
27
Joy District
Revisit Joy District to enjoy it's rooftop views and energetic ambiance once more—an essential stop for anyone exploring Chicago's nightlife scene.
28
Pride & Joy Pavilion
Roar with excitement at the Kovler Lion House, nestled by Lake Michigan Shoreline. A thrilling outdoor experience awaits as you encounter majestic lions in their naturalistic habitat.
29
Gibbalicious Groove House
Swing by the Brach Primate House for an engaging outdoor activity in Chicago. Witness diverse primates in habitats that mimic their natural environments, right here in the Second City.
30
The Feathered Terminal
Listen closely at McCormick Bird House where nature's music fills the air. An ideal outdoor activity for bird enthusiasts visiting Chicago's Magnificent Mile area.
31
Bearbnb: The Chilly Suite
Explore Millennium Park, a must-see in the Windy City. Stroll through it's lush gardens and marvel at public art like the iconic Cloud Gate. Perfect for outdoor activities and sightseeing.
32
The Great Migration Hangout
Discover Navy Pier, a vibrant spot on the Lake Michigan Shoreline. Ideal for outdoor things to do, enjoy rides, gardens, and breathtaking views of Chicago attractions.
33
Banana-Rama Onsen Oasis
Explore the Windy City's Millennium Park, a must-see for outdoor enthusiasts. Stroll through lush gardens, enjoy live music at the Jay Pritzker Pavilion, and admire the iconic Cloud Gate sculpture.
34
Critter City Safari
Explore the Windy City's vibrant outdoor scene. Discover hidden gems along the Chicago Riverwalk or enjoy a leisurely stroll by Lake Michigan's shoreline. Perfect for those seeking unique outdoor activities.
35
Contemplative Women by FEDZ
Discover FEDZ's vibrant mural in The Loop, a must-see for art lovers. This outdoor masterpiece blends street style with California flair, making it a unique Chicago attraction.
36
Lunar New Year by Layqa Nuna Yawar
Explore this poignant mural in Chi-Town, where cultural history meets art. It's a powerful outdoor piece that locals recommend for it's storytelling and vibrant textures.
37
Mixed-Media by Amuse126
Amuse126's mural is an urban gallery favorite, showcasing graffiti and surrealism. Experience this open-air art stop, celebrated as one of Chi-Town's best outdoor attractions.
38
Mixed-Media Surrealism by Unknown
Uncover the mystery of this Dali-inspired mural in Chi-Town. It's surreal visuals and hidden details offer a fresh adventure for those exploring Chicago's public art scene.
39
The Resurrection Project by Elevarte
This quilt-like mural mixes tech and tradition, creating a unique visual experience in Chicago. Locals hail it as a hidden gem on any city art walk.
40
Frederick C. Robie House
Explore the architectural marvel of the Frederick C. Robie House in Chi-Town. It's intricate design is a must-see for architecture enthusiasts visiting Chicago.
41
DuSable Museum of African American History
Visit the DuSable Museum, a key site for outdoor activities in Chicago's cultural scene. It's an essential stop for those interested in African American history.
42
Washington (George) Park
Stroll through Washington Park, where nature meets art in The Windy City. This green oasis is perfect for outdoor activities and enjoying Chicago's natural beauty.
43
Rockefeller Memorial Chapel
Admire the Rockefeller Memorial Chapel's stunning exterior on your next outdoor adventure in Chicago. It's a serene spot amidst the bustling cityscape.
44
Joe and Rika Mansueto Library
Marvel at the futuristic design of Joe and Rika Mansueto Library during your outdoor exploration of The Second City. It's an architectural wonder worth seeing.
45
The Renaissance Society
Engage with contemporary art at The Renaissance Society, an ideal spot for cultural outdoor activities in The Loop area of Chicago.
46
University of Chicago Botany Pond
Relax by the University of Chicago Botany Pond, a peaceful retreat perfect for outdoor activities amidst Chi-Town's hustle and bustle.
47
Oriental Institute Museum
Explore ancient artifacts at the Oriental Institute Museum during your cultural outing in The Windy City. It's an enriching experience for history lovers.
48
Wrigley Field
Experience the excitement outside Wrigley Field, where the spirit of the Cubs fills the air. Capture a photo by the iconic marquee and feel the energy of Chi-Town's baseball legacy.
49
Wrigley Rooftops
Discover Wrigley Rooftops, where fans enjoy games from above. This unique spot offers a one-of-a-kind view of Chicago's beloved Cubs in action, perfect for sightseeing in The Windy City.
50
Jeni's Splendid Ice Creams
Indulge your sweet tooth at Jeni's Splendid Ice Creams. This local favorite serves up inventive flavors that delight visitors exploring Chi-Town's vibrant culinary scene.
51
Swift & Songs Tavern
Outside Swift & Sons Tavern, enjoy Wrigleyville’s lively ambiance. This spot offers a taste of local culture with it's unique blend of artful details and vibrant energy.
52
Chicago Fire Department
Visit the historic firehouse in Wrigleyville to appreciate it's architectural charm. Learn about it's role in Chicago's rich history as you explore this neighborhood landmark.
53
Metro
Feel the rhythm at Metro, Chicago's music hub. This venue pulses with live performances that captivate visitors seeking unique nightlife experiences in The Loop.
54
Gallagher Way
Relax at Gallagher Way near Wrigley Field. This open space invites you to enjoy community events or simply unwind amidst Chi-Town's vibrant atmosphere.
55
Wrigleyville Peace Pole
Reflect at Wrigleyville Peace Pole in it's serene park setting. This monument promotes unity with it's powerful messages—an inspiring stop on any Chicago exploration.
56
Albert F. Madlener House
Appreciate the Albert F. Madlener House, an architectural marvel by Richard E. Schmidt. It's unique design is a highlight for visitors to Chi-Town.
57
International Museum of Surgical Science
Visit the International Museum of Surgical Science to explore medical history outdoors. It's stately exterior invites curiosity about surgical advancements.
58
Charnley-Persky House
Admire Charnley-Persky House, an architectural treasure designed with intricate details that captivate visitors exploring Gold Coast gems.
59
Chicago History Museum
Explore this landmark and soak up it's vibrant energy—it's a Gold Coast must-see for outdoor activity fans and city tours alike.
60
Greene Vardiman Black
Capture a creative team photo with this bronze legend on your walking tour—a quirky stop in Gold Coast.
61
Abraham Lincoln Monument
This iconic spot blends sightseeing with history—let whimsy guide your hunt for hidden details at this outdoor attraction.
62
Robert Cavelier de La Salle
Decode clues about this intrepid figure—from art appreciation to photo missions, adventure awaits in the 312.
63
Abraham Lincoln Center
Discover the Abraham Lincoln Center in The 312, a must-see for outdoor enthusiasts. Capture it's historic essence and enjoy a day trip filled with local trivia and unique things to do.
64
The Light of Truth Ida B. Wells National Monument
Explore the Light of Truth monument, an outdoor gem blending history and art. Enjoy sightseeing while uncovering Chicago's spirit through engaging activities.
65
The Ida B. Wells Homes
Visit the historic Ida B. Wells Homes, a pivotal location in Groveland Park's history. Engage in outdoor activities while discovering hidden gems of local trivia.
66
Victory, World War I Black Soldiers Memorial
The Victory Memorial is a must-see for those exploring Chicago's rich history. Enjoy outdoor activities as you learn stories of heroism and capture memorable moments.
67
Stephen Arnold Douglas
Explore Douglas's memorial, an outdoor landmark that invites visitors to discover historic buildings and enjoy team challenges.
68
Sunset Cafe
Channel jazz legends at Sunset Cafe, an outdoor highlight for art lovers and history buffs seeking unique experiences in Chicago.
69
Marianos Hebru Brantley Mural
Scout out Hebru Brantley's vibrant mural, an outdoor attraction that fuels curiosity with it's bold artwork and engaging activities.
70
Firefighters Memorial
Honor Chicago's brave Volunteer Firefighters at this historic memorial. Learn about their legacy and enjoy a peaceful outdoor visit to this meaningful site.
71
Frances E. Willard
Discover Frances E. Willard's legacy in Chicago. This historical marker celebrates her contributions to women's rights and is an inspiring outdoor activity for visitors.
72
Battery A Chicago Light Artillery
Reflect on history at Battery A Chicago Light Artillery memorial. The inscriptions tell stories of bravery, making it a poignant stop for visitors.
73
George B. Armstrong
Learn about George B. Armstrong's contributions to mail service at this historic site. It's an engaging stop for those exploring Chicago's postal history.
74
Service Mens Club World War Memorial
Visit the Service Mens Club World War Memorial to honor wartime heroes with it's impressive granite structure and thoughtful inscriptions.
75
Chicago Board of Trade Battery
Uncover history at the Chicago Board of Trade Battery plaque, where tales of past battles come alive for curious explorers.
76
Park No. 599
Wander through this Lakefront Gem, where locals host impromptu picnics and playful squirrels abound. Enjoy a relaxing outdoor experience along the vibrant Lake Michigan Shoreline.
77
Fireside Tavern & Grill
Admire the inviting exterior and imagine laughter spilling into the street as you explore neighborhood history.
78
North Avenue Baths Facade
Explore the historic charm of North Avenue Baths, now a bustling gastropub. Discover Wicker Park's vibrant past while enjoying it's modern flair. A must-see for those seeking unique Chicago attractions.
79
Former Home of MTV’s “The Real World Chicago"
Stand where reality TV history was made at the Real World Chicago house. A pop culture landmark in Chi-Town, perfect for fans and explorers alike. Capture the moment on your sightseeing adventure.
80
Quimbys Bookstore
Discover Quimbys Bookstore's quirky charm on this outdoor adventure. It's wild window displays and indie posters capture Wicker Park's alternative spirit - a unique thing to do in Chicago.
81
Wicker Park
Experience Wicker Park's vibrant pulse through it's storied trees and local art installations. This outdoor haven is ideal for teamwork challenges and capturing Chi-Town's lively essence.
82
Coyote Building
Marvel at the Coyote Building's striking silhouette, an iconic landmark in The Loop. Locals say spotting the little coyote brings luck - will you find it during your visit?
83
Garfield Park Conservatory
Stroll through Garfield Park Conservatory, an oasis in Chi-Town offering lush greenery and serene beauty amidst urban life.
84
Lincoln
Admire Lincoln, the Railsplitter statue at Garfield Park—a striking piece by Jules Berchem that's a must-see for art lovers visiting The Loop.
85
Garfield Park Fieldhouse
Explore the Windy City's outdoor gems along the Chicago Riverwalk. Feel the city buzz as you stroll past public art and riverside cafes. Locals say sunset here is pure magic.
86
Bulls with Maidens
Discover outdoor fun in the Windy City as you stroll The Loop and spot hidden art along the Chicago Riverwalk. Locals say sunrise here is unforgettable. Enjoy fresh air and Chi-Town energy on your adventure.
87
Garfield Park Bandshell
Discover outdoor fun in the Windy City. Stroll by iconic architecture, feel the buzz of The Loop, and catch breezes from Lake Michigan. Locals say you will spot hidden art along the Chicago Riverwalk.
88
Legler Library
Explore this spot in the heart of the Windy City, where locals gather for fresh air and city vibes. Stroll past unique architecture and catch glimpses of the Chicago Riverwalk nearby.
89
Cloud Gate
Visit Cloud Gate, or 'The Bean,' in Millennium Park. This reflective sculpture is a must-see for first-time visitors, offering unique photo ops and a playful view of Chicago's skyline.
90
Crown Fountain
Crown Fountain in Millennium Park is an engaging outdoor experience. Watch as LED faces animate with water displays, creating a lively spot for locals and tourists alike.
91
The Art Institute of Chicago
Outside The Art Institute, admire the bronze lions guarding this historic museum. It's a perfect spot for art lovers exploring Chicago's rich cultural scene.
92
Buckingham Fountain
Buckingham Fountain dazzles with it's choreographed water displays set to music. Located in Grant Park, it's a picturesque spot for sightseeing along Lake Michigan.
93
Museum Campus
Stroll through Museum Campus for panoramic views of Chicago's skyline along Lake Michigan. It's perfect for nature lovers seeking cultural enrichment at world-class institutions.
94
The Green Mill
95
The Drake Hotel
96
The Pump Room
97
Biograph Theater
98
The Redhead Piano Bar
99
Holy Name Cathedral
100
Exchequer Restaurant & Pub
101
Three Arts Club Cafe
102
The Statue of the Republic
Explore Millennium Park, a vibrant outdoor space in the heart of Chi-Town. From the iconic Cloud Gate to lush gardens, this park offers a refreshing escape. Perfect for a leisurely stroll or a day trip.
103
Wooded Island
Stroll along Navy Pier's Lake Michigan Shoreline for breathtaking views and outdoor fun. This lively spot is ideal for sightseeing and enjoying Chi-Town's fresh air.
104
Bobolink Meadows
Gaze at Chicago from above at Willis Tower's Skydeck. This outdoor activity offers panoramic views of The Loop and beyond, making it a recommended thing to do in Chi-Town.
105
Garden of the Phoenix
Wander along the Chicago Riverwalk, where the city's vibrant life meets serene waters. This outdoor gem is perfect for sightseeing and soaking in Chi-Town's atmosphere.
106
Joseph Regenstein Library
Discover outdoor gems in the Windy City. Explore vibrant murals, bustling parks, and riverfront paths. Locals know the best photo ops are just off The Loop. Feel Chicago's energy under open skies.
107
Cobb Lecture Hall
Stroll along the Chicago Riverwalk for fresh air and city buzz. Watch kayaks glide by and street performers entertain. Insiders say sunset here is a must-see for first-time visitors seeking outdoor fun.
108
Hammond Library
Millennium Park is where locals picnic on lush lawns and snap selfies at Cloud Gate. Outdoor art and gardens make it a must-see stop on any Windy City adventure—especially during summer concerts.
109
Saieh Hall For Economics
Navy Pier buzzes with lakeside energy—catch breezes from Lake Michigan as you stroll past carnival rides and gardens. Local trivia: Fireworks light up the sky every Wednesday and Saturday in summer.
110
Harper Memorial Library
Willis Tower's Skydeck draws crowds outdoors for jaw-dropping city views. On clear days, you can spot four states! Locals recommend timing your visit at dusk for an unforgettable Windy City panorama.
111
University of Chicago Botany Pond
The Magnificent Mile offers open-air shopping and historic architecture under towering skyscrapers. Locals love window-shopping here—look up to spot ornate facades from Chicago's golden age.
112
Paul V Galvin Library
Discover outdoor fun in the Windy City as you stroll past iconic landmarks and vibrant street art. Feel the buzz of The Loop and catch glimpses of the Chicago Riverwalk on your adventure.
113
Main Building
Soak up Chicago's energy with an outdoor journey along Lake Michigan Shoreline. Snap photos of famous architecture and enjoy people-watching in bustling public spaces near Navy Pier.
114
Pluie de Soleil
Experience the Second City's outdoor spirit by tracing paths lined with public art and hidden gardens. Locals say you might spot a secret mural or two along your route.
115
Series No 36 Glass and Bronze
Wander through open plazas where locals gather for festivals and pop-up markets. Feel the pulse of Chicago attractions under the city lights as you explore outdoor spaces after sunset.
116
Keating Sports Center
Take in fresh air along tree-lined boulevards and historic bridges. Outdoor activities here reveal stories only locals know, like which bridge offers the best skyline view at golden hour.
117
S.R. Crown Hall (IIT)
Step outside for a taste of Chicago's outdoor culture—think riverfront walks and lakeside breezes. You might even stumble upon a pop-up art installation or live music event.
118
Mundelein Center Annex
Discover outdoor gems along the Chicago Riverwalk, where locals stroll and soak up Windy City vibes. Snap a photo of the public art or catch live music echoing through The Loop.
119
Mundelein Center for the Fine and Performing Arts
Wander Millennium Park for outdoor art, splashy fountains, and skyline views that scream Chi-Town. Locals say early mornings here offer peaceful moments before crowds arrive.
120
Madonna Della Strada Chapel
Stroll Navy Pier for classic Windy City fun: carnival rides, lakeside paths, and unbeatable people-watching. Insider tip: sunsets from the pier are pure magic over Lake Michigan.
121
Cudahy Library
Take in Willis Tower from street level for a sky-high perspective of The Loop. Locals love spotting reflections of clouds on it's glass facade—especially after a summer rain.
122
Loyola University Lakeshore Campus peace pole
Meander along the Lake Michigan shoreline for fresh breezes and city skyline views. Early risers catch joggers and cyclists greeting the day—an authentic slice of Chi-Town life.
123
Joseph J Gentile Arena
Explore the hidden corners of The Loop where street art pops up unexpectedly. Locals know lunchtime brings food trucks and impromptu performances to these bustling blocks.
124
The Biograph
Step outside and discover the Windy City's outdoor gems. From the Chicago Riverwalk to Millennium Park, Chi-Town's fresh air adventures are perfect for explorers seeking local flavor and fun.
125
Holtschneider Performance Center
Explore The Loop's lively streets and catch a breeze off Lake Michigan. Outdoor activities abound, from riverside strolls to public art hunts, making every visit a new adventure in the heart of Chi-Town.
126
Cortelyou Commons
Wander through Millennium Park and feel the pulse of Chicago outdoors. Locals know you can spot cloud reflections on The Bean at sunrise—a Windy City secret worth catching during your adventure.
127
Sullivan Athletic Center
Take in the sights along the Chicago Riverwalk where kayakers glide past city landmarks. Outdoor enthusiasts love this spot for people-watching and uncovering local trivia etched into riverfront plaques.
128
John T. Richardson Library
Catch breezes near Navy Pier as you explore open-air art installations and street performers. Insiders say sunset here paints the skyline with colors you will not forget—a true Chi-Town experience.
129
DePaul University Bookstore
Stroll beneath Willis Tower's towering shadow where locals gather for outdoor festivals and pop-up markets. The plaza buzzes with energy—perfect for those chasing authentic Second City moments.
130
The McCallister House
Discover outdoor gems along the Lake Michigan shoreline in Chi-Town. The Windy City is full of quirky art and hidden gardens. Locals say you might spot a jazz musician busking near The Loop on sunny days.
131
The Murphys’ House
Take in fresh air as you walk through Millennium Park, where locals love the outdoor sculptures and lively energy. Watch for pop-up performances—Chi-Town always has a surprise waiting for explorers.
132
Grand Food Center
Stroll along Navy Pier’s waterfront paths for classic outdoor fun in the Second City. Locals know sunset views from here are unbeatable, especially when Lake Michigan breezes roll in during summer evenings.
133
Former Hubbard Woods Pharmacy
Experience outdoor adventure at the Chicago Riverwalk, where you can spot kayakers gliding past city landmarks. The Windy City’s riverfront buzzes with activity—insiders recommend visiting during golden hour.
134
Hubbard Woods Park
Wander through The Loop’s open plazas dotted with modern sculptures and fountains. You might stumble upon pop-up food trucks or local musicians—Chicago’s downtown always keeps things lively outdoors.
135
Hubbard Woods Metra Station & Footbridge
Enjoy lakeside breezes along the Lake Michigan shoreline—a favorite spot for joggers and cyclists. Locals say early mornings offer peaceful views before Chi-Town wakes up to it's energetic rhythm.
136
“Talk to Santa” Spot
Take your adventure outside at Willis Tower Plaza—admire this iconic skyscraper from below while soaking up city vibes. Local tip: look up at night to see it's lights change colors for special occasions.
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Firehouse 51
Discover outdoor gems in the Windy City. Explore unique corners along the Chicago Riverwalk or catch local art on The Loop streets. Feel Chi-Town energy as you stroll past iconic architecture and vibrant murals.
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Cinespace Chicago Film Studios
Enjoy outdoor activities in Chicago with a walk near Navy Pier or through lush parks. Spot local wildlife, snap photos of city views, and soak up the lakeside breeze that makes Chi-Town unforgettable.
139
“Molly’s Pub”
Step out into Chicago attractions where locals gather. Whether you are tracing history on The Loop or relaxing by Lake Michigan, you will find fresh air, city sounds, and plenty of outdoor fun to enjoy.
140
Gaffney Chicago Medical Center
Uncover outdoor things to do in Chi-Town by following trails near Willis Tower or relaxing at Millennium Park lawns. Locals say sunsets here paint the skyline in unforgettable colors—bring your camera!
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Casey & Dawson’s apartment
Explore outdoor activities along the Lake Michigan shoreline—watch sailboats drift by or join locals jogging the paths. Insider tip: early mornings offer peaceful moments before crowds arrive.
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Severide’s loft
Head outside for fresh perspectives on Chicago attractions—find hidden sculptures, listen for street musicians, and enjoy breezes off Lake Michigan. Locals love these little surprises around every corner.
143
UIC Police Station
Take an outdoor break in The Loop—admire historic facades, spot quirky public art, and feel the pulse of downtown life. Even longtime residents discover new details on these lively city walks.
144
Mr. Beef on Orleans
Explore the Windy City outdoors and discover hidden gems along the Chicago Riverwalk or near Millennium Park. Locals say the best street art pops up after a rainstorm—see if you can spot it on your adventure.
145
Lou Mitchell’s
Stroll through Chi-Town's vibrant neighborhoods for outdoor fun. The Magnificent Mile offers more than shopping—look up for quirky rooftop gardens locals adore, especially in spring.
146
avec (West Loop)
Enjoy outdoor activities along the Lake Michigan shoreline, where breezes keep things cool even in summer. Watch for kayakers racing by—locals say sunset paddles are unforgettable.
147
Publican Quality Meats
Wander near Willis Tower and feel the pulse of downtown Chicago attractions. Outdoor plazas often host spontaneous dance battles—locals love showing off their moves when least expected.
148
Ever Restaurant
Take in fresh air while exploring art galleries with outdoor installations around Millennium Park. Locals whisper that early mornings offer the best light for photos and peaceful moments.
149
Kasama
Roam the Chicago Riverwalk for must-see views and riverside relaxation. Watch out for kayaks gliding by—some locals race each other under bridges, adding excitement to your walk.
150
Margie’s Candies
Step outside into Second City's lively parks where festivals fill the air with music and laughter. Locals recommend checking out community gardens—they are full of surprises every season.
151
Winslow House
Explore the Windy City outdoors, where the Chicago Riverwalk and Lake Michigan Shoreline invite you to soak up city vibes. Locals say the best people-watching happens near The Loop on sunny afternoons.
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Irv Kupcinet (Wabash Ave) Bridge – the bike shot
Experience outdoor activities in Second City with fresh air and skyline views. The Riverwalk buzzes with energy, and you might spot kayakers gliding by—insider tip: sunsets here are unforgettable.
153
“Chicago Chronicle” exterior (reused shot) – London Guarantee/Crain Building
Wander through Chi-Town's vibrant parks and discover public art tucked between skyscrapers. Outdoor explorers often find hidden murals that only locals know about—perfect for your next day trip.
154
Wrigley Building
Step outside and let Chicago's energy guide you—Millennium Park's gardens bloom with color, while the Riverwalk hums with laughter. Did you know locals picnic here during summer festivals?
155
Chicago Riverwalk
Take a stroll down the Magnificent Mile for fresh air and window shopping. Outdoor enthusiasts say early mornings offer peaceful moments before crowds arrive—a local secret worth trying.
156
Marina City
Enjoy outdoor fun as you pass by Willis Tower's towering presence—locals love it's shadow play at sunset. The area offers a unique blend of city buzz and quiet corners for reflection.
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Willis Tower
Discover outdoor gems in the Windy City. Stroll along the Chicago Riverwalk or explore art installations near Millennium Park. Locals say you might spot hidden murals only Chi-Town insiders know about.
158
Art Institute of Chicago
Enjoy outdoor activities in Second City by exploring green spaces and public art. The Loop offers a lively vibe, and you may find secret gardens tucked between iconic skyscrapers—an insider's delight!
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Daley Plaza / Dearborn Street
Step outside and take in Chi-Town's vibrant street scenes. Walk the Lake Michigan shoreline or relax at Navy Pier. Locals whisper about a hidden spot with unbeatable skyline views—try to find it!
160
Chicago Board of Trade Building
Outdoor adventures await along the Chicago Riverwalk, where you can watch boats glide by or spot local musicians playing tunes. Some say there is a secret staircase leading to river-level murals.
161
“Chez Quis” Exterior
Explore Chicago's outdoor wonders by visiting lively plazas and green parks in The Loop. Watch for pop-up art installations—locals often know when they appear before anyone else does!
162
Parking Garage
Take a stroll along the Magnificent Mile for outdoor shopping and people-watching. Look closely—there are brass plaques honoring famous Chicagoans that many visitors miss but locals always spot.
163
Wrigley Field
Venture outside for fresh air along Lake Michigan's shoreline, perfect for a leisurely walk or bike ride. Some say early mornings reveal peaceful scenes only true Chicagoans experience.
164
Old Chicago Main Post Office
Step outside and soak up the Windy City vibe along the Chicago Riverwalk. Watch kayaks glide by, spot local art, and catch a breeze that locals swear is stronger near The Loop.
165
200 W Randolph Parking Garage
Wander the Lake Michigan shoreline for fresh air and unbeatable city views. Locals love catching sunrise here, and you might spot playful seagulls racing the waves on breezy mornings.
166
Daley Plaza
Stroll through Millennium Park to see public art and green spaces in the heart of The Loop. Locals know the Crown Fountain is extra lively after rain—watch out for surprise splashes!
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South LaSalle Street “Canyon
Catch street performers and lake breezes at Navy Pier. The Ferris wheel lights up at night, but locals say sunset from the pier is unbeatable for soaking in Chi-Town's skyline glow.
168
IBM Building / AMA Plaza
Take in panoramic city views from Willis Tower's Skydeck ledge—if you dare! On clear days, locals claim you can spot four states from this legendary Second City perch.
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Illinois Center
Walk down Magnificent Mile to window shop designer stores or admire historic architecture. Locals know some buildings hide quirky details if you look up while strolling.
170
Wyndham Grand
Explore lush gardens and quiet corners at Grant Park. Locals flock here during summer festivals—bring a picnic or people-watch as you soak up classic Windy City charm outdoors.
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Trump International Hotel & Tower
Follow the river through The Loop on a self-guided adventure along the Chicago Riverwalk. Watch tour boats cruise by and spot murals that change with each season—locals love finding new ones.
See our Top Outdoor Activities By Neighborhood
From artistic Wicker Park to historic Hyde Park and bustling Andersonville, each neighborhood offers it's own flavor of outdoor adventure in Chicago. Discover secret murals, local hotspots, and unexpected challenges as you explore these vibrant districts—click on these neighborhoods to see the related activity.
12,000+ Reviews For our Hunts
See what people say about our outdoor activities in Chicago
Thousands have raved about our outdoor activities in Chicago—families love how engaging they are and teams appreciate the camaraderie they inspire! With five-star reviews pouring in daily like ‘Best way to discover Chi-Town!’, it is clear why visitors trust us for memorable adventures across Illinois.
This is definitely one of the best things to do in Chicago. The interactive nature kept it exciting throughout!
Daniel W.
We had an awesome time on our date night experience in downtown Chicago. It was fun and brought us closer together!
Megan L.
A great walking tour of Lincoln Park neighborhood! It was engaging and offered insights into places I'd never noticed before.
James H.
This was such a cool experience in West Town! I loved uncovering local treasures and learning about their history.
Laura M.
FAQs.
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LOCAL INSIGHTS
Fun Chicago Facts and Hidden Gems
Did you know that Chicago was rebuilt after the Great Fire of 1871? It's innovative spirit gave rise to world-famous architecture along Lake Michigan’s shoreline.
The city’s nickname ‘The Windy City’ is not just about breezes off Lake Michigan—it also nods to it's history of passionate politics! Every corner has a story waiting for curious day
The city’s nickname ‘The Windy City’ is not just about breezes off Lake Michigan—it also nods to it's history of passionate politics! Every corner has a story waiting for curious day
© 2016-2025 Let's Roam, LLC. Let’s Roam® is a registered trademark. All Rights Reserved.
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