Top Outdoor Activities In Chicago, Illinois

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.

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?

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.

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!

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!

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Cosmic Ray Detectors

Discover the Cosmic Ray Detectors on campus, an intriguing piece of technological history perfect for an educational outdoor activity in Chi-Town.

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.

The Renaissance Society

Engage with contemporary art at The Renaissance Society, an ideal spot for cultural outdoor activities in The Loop area of Chicago.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Charnley-Persky House

Admire Charnley-Persky House, an architectural treasure designed with intricate details that captivate visitors exploring Gold Coast gems.

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.

Greene Vardiman Black

Capture a creative team photo with this bronze legend on your walking tour—a quirky stop in Gold Coast.

Abraham Lincoln Monument

This iconic spot blends sightseeing with history—let whimsy guide your hunt for hidden details at this outdoor attraction.

Robert Cavelier de La Salle

Decode clues about this intrepid figure—from art appreciation to photo missions, adventure awaits in the 312.

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.

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.

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.

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.

Stephen Arnold Douglas

Explore Douglas's memorial, an outdoor landmark that invites visitors to discover historic buildings and enjoy team challenges.

Sunset Cafe

Channel jazz legends at Sunset Cafe, an outdoor highlight for art lovers and history buffs seeking unique experiences in Chicago.

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.

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.

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.

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.

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.

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.

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.

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.

Fireside Tavern & Grill

Admire the inviting exterior and imagine laughter spilling into the street as you explore neighborhood history.

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.

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.

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.

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.

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?

The Violet Hour

Seek out The Violet Hour's mysterious entrance cloaked in ever-changing art. Finding the hidden handle is a rite of passage in The City of Big Shoulders - an intriguing outdoor activity.

1994: Sears Roebuck & Company Mail Order Plant, Merchandise Building

Explore the historic Sears Roebuck site, a key piece of Chicago's industrial past. Walk around the complex and imagine the bustling mail order operations that once defined this landmark.

1994: Sears Roebuck & Company Mail Order Plant, Merchandise Building view SE

Discover the architectural beauty of the Sears plant, designed by Nimmons & Fellows. This outdoor adventure offers a glimpse into Chicago's vibrant industrial era.

Garfield Park Conservatory

Stroll through Garfield Park Conservatory, an oasis in Chi-Town offering lush greenery and serene beauty amidst urban life.

Robert Burns

Stand before the Robert Burns plaque and appreciate it's literary significance. This tribute to Scotland’s poet adds cultural depth to your Chicago exploration.

Lincoln, the Railsplitter statue, Garfield Park

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.

1908: Sears Roebuck & Company Mail Order Plant, printing and advertising

Visit this historical site where Sears' printing operations thrived. Engage with it's storied past through outdoor exploration in Garfield Park.

1994: Sears Roebuck & Company Mail Order Plant, printing building

Explore the largest building of Sears' plant designed by Nimmons & Fellows. It's bustling history offers insight into Chicago’s industrial evolution.

1964: Sears Roebuck & Company Mail Order Plant, administration building

Revisit one of Sears’ major buildings from 1964. This outdoor experience lets you engage with Chicago’s rich industrial narrative.

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.

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.

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.

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.

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.

The Green Mill

The Drake Hotel

The Pump Room

Biograph Theater

The Redhead Piano Bar

Holy Name Cathedral

Exchequer Restaurant & Pub

Three Arts Club Cafe