100 Things to Do in Chicago, a Bucket List City

FOMO is real! Do you worry about overlooking something incredible when travel planning? If so, then you’re in luck because this curated list of 100 things to do in Chicago Illinois will ensure you create an unforgettable and personalized vacation including landmarks, attractions, museums, outdoor activities, beaches, where to eat and shop, and where to get the perfect photos for lasting memories. Don’t skip the Plan Your Trip section for when to go, how long to stay, what to pack, how much to budget, where to stay, and how to get around.

Chicago is famous for jazz music, 1920s gangsters, and Oprah Winfrey but there is so much more to the Windy City. You will find a skyline comparable to New York City, a riverwalk cutting through the heart of the city, amazing shopping, a theater district, some of the best museums in the world and so much more. It’s all here, keep reading for 100 Things to Do in Chicago.

READ Chicago Illinois Weekend Itinerary, the Best Things to Do

100 Unforgettable Things to Do in Chicago Illinois

Top 5 Things to Do in Chicago

• Chicago River Architecture Tour.
• View the city from above on an observation deck.
• See the Crown Fountain and Cloud Gate in Millenium Park.
• Watch the Buckingham Fountain Light and Water Show.
• Go shopping on the Magnificent Mile (Michigan Ave).

Must Do Attractions and Activities in Chicago

• Catch the free firework show at Navy Pier Memorial Day through Labor Day.
• Walk onto a glass ledge 1400 feet in the air at the Willis Tower and Skydeck.
• Admire Cloud Gate (The Bean) and splash around in the Crown Fountain at Millennium Park.
• Catch the Buckingham Fountain water and light show, hourly from May through October.
• Tour Wrigley Field, home of the Chicago Cubs, and check out Wrigleyville.
• Say hello to rescued Beluga whales and dolphins at the Shedd Aquarium.
• Stop by the free Lincoln Park Zoo and visit the polar bears and apes.
• Tilt over the city and see the cars below at 360 CHICAGO Observation Deck.
• Explore the neighborhoods of Old Town, Logan Square, and Wicker Park.
• Take the Chicago Theatre Marquee Tour and stand on the stage of the famous theater.
• Get tickets to a Broadway show in the Chicago Theatre District.
• Catch the show at Second City Comedy Club, the birthplace of improv.
• Hear stories about Scarface, Al Capone, The Untouchables, and the Chicago Mob on a Gangster Tour through the city.
• Explore the secret underground passageways of Chicago’s Pegway.
• See a performance at the Lyric Opera.
• Visit the Palm House, the Fern Room, the Orchid Room, and the Show House at the Lincoln Park Conservatory, reservation is required.
• See the largest Tiffany stained-glass dome in the world at the Chicago Cultural Center.
• Take in the best of the city from the water on the Chicago Architecture River Cruise.
• See a classic at the Chicago Shakespeare Theater.
• Tour the Robie House, designed by the famous architect Frank Lloyd Wright.
• See the historic start of Route 66, America’s Main Street.
• Walk across the BP Pedestrian Bridge connecting Millennium Park to Lake Michigan.
• Watch a performance of the Joffrey Ballet.
• Learn about Chicago during the 1920s in an Art Deco Tour.

TIP: Save money by purchasing the Chicago CityPass. Pick 5 attractions and save almost 50%! Options include the Art Institute of Chicago, Shoreline Sightseeing Architecture River Tour, 360 CHICAGO Observation Deck, Skydeck Chicago, Shedd Aquarium, Adler Planetarium, Field Museum, or Museum of Science and Industry. I used it and loved that it told me which attractions required reservations. I saved money and everything was planned ahead of time so I could just enjoy while there. 

Best Museums in Chicago

• Check out the street art along the Wabash Arts Corridor.
• Watch the Art on theMart free digital art projection show on the Riverwalk, April through December.
• Browse works by Vincent van Gogh, Pablo Picasso, Claude Monet, Georgia O’Keeffe, and Grant Wood at the Art Institute of Chicago, the second-largest museum in North America.
• See a WWII German submarine and a recreated coal mine at the Museum of Science and Industry.
• Check out the natural history exhibits and say hello to Sue, the famous T-Rex skeleton at the Field Museum.
• Learn about astronomy and astrophysics and catch the show at the Adler Planetarium.
• Discover Mexican art and culture in Pilsen at the National Museum of Mexican Art.
• Learn about local flora and fauna in Lincoln Park at the Peggy Notebaert Nature Museum.
• Learn about the Great Chicago Fire at the Chicago History Museum.
• Visit the DuSable Museum, the country’s first museum of African-American heritage and culture.
• Browse works created 1920 to the present day at the Museum of Contemporary Art.
• Explore the medical history and exhibits at the International Museum of Surgical Science.
• See ancient artifacts from the Middle East at the Oriental Institute Museum.
• Enjoy interactive exhibits for kids of all ages at the Chicago Children’s Museum.
• Learn about Greek history and culture in America at the National Hellenic Museum.
• Explore the history of radio and television at the Museum of Broadcast Communications.
• Learn about your favorite authors at the American Writers Museum.
• Stop by the Chicago Sports Museum and dive into Chicago’s sports history and legends: The Bears, the Bulls, the Cubs, the White Sox, and the Blackhawks.
• Tour a Gilded Age mansion at the Richard H. Driehaus Museum.
• Discover art from diverse cultures and periods at the Smart Museum of Art.

Outdoor Activities in Chicago

• Grab a cup of coffee and take the Riverwalk to Lake Michigan.
• Learn about the city’s stunning architectural history on the Chicago River Architecture Cruise.
• Paddle along the lakefront and capture stunning views in a kayak on Lake Michigan.
• Bike on the Lakefront Trail and take in the beautiful waterfront scenery on two wheels.
• Attend free concerts at the Jay Pritzker Pavillion Millennium Park Concerts.
• Watch the Buckingham Fountain water and light in Grant Park, hourly from 9 a.m. to 11 p.m. from May to October.
• Walk the elevated 606 Trail, Chicago’s Highline.
• Visit the Osaka Garden and see the cherry blossom trees in the spring at Jackson Park.
• Head to Humboldt Park and paddle the lagoon in a swan boat.
• Wander through beautiful landscapes and the golden dome pavilion in Garfield Park.
• Stop by the Alfred Caldwell Lily Pool and experience a serene garden oasis in Lincoln Park.
• Get some sun at Oak Street Beach, Ohio Street Beach, or North Avenue Beach.
• Take a walk on the Lincoln Park Nature Boardwalk.
• Walk through the Crystal Gardens on the Navy Pier.
• Hike the Northly Islands trails.

Where to Eat in Chicago

• Stop for coffee at Starbucks Reserve, the largest Starbucks in the world, and don’t miss the rooftop deck.
• Enjoy a brownie where they were created, the Palmer Hotel.
• Grab lunch from a vendor at the Revival Food Hall or Fulton Market.
• Head to Restaurant Row (Randolph Street) for a casual dinner out.
• Eat Deep-Dish Pizza, a Chicago-style specialty, at pizzerias like Lou Malnati’s or Giordano’s.
• Eat a Chicago-style hot dog and chocolate cake shake at Portillo’s.
• Stop at Al’s Italian Beef and try their sandwich.
• Dine at Girl & the Goat, Top Chef winner Stephanie Izard’s acclaimed restaurant.
• Experience innovative fine dining with a multi-course tasting menu at Alinea.
• Savor Italian cuisine and shop for gourmet ingredients at Eataly.
• Dine at RPM Italian, a restaurant offering modern Italian cuisine.
• Taste farm-to-table dishes and craft beers at The Publican.
• Eat the best cheeseburger in America at Au Cheval and see if you agree.
• Enjoy creative Chinese fare with a modern twist at Duck Duck Goat.
• Satisfy your cravings with comfort food and delicious baked goods at Little Goat Diner.
• Sample Italian small plates and wine at Quartino Ristorante.
• Dine with a view high above the city at The Signature Room at the 95th.
• Indulge in high-quality steaks and seafood at RPM Steak.

Chicago Nightlife: Pubs, Cocktails and Nightclubs

• Take a shot of Marlot, a Chicago specialty liquor.
• Spend an evening at The Green Mill, a historic jazz club once frequented by Al Capone.
• Go bar hopping in Wicker Park.
• Enjoy cocktails with a waterfront view in a Chicago Riverwalk bar.
• Listen to live blues music at Kingston Mines or Buddy Guy’s Legends.
• Stop by Three Dots and A Dash tiki bar for island-inspired drinks.
• Sip cocktails with stunning views of the city at venues like Cindy’s, LH ON 22, Raised, Cerise, VU, Upstairs at the Gwen, or J. Parker.
• Stop in The Violet Hour for craft cocktails in a trendy speakeasy.
• Relax at the Offshore Rooftop & Bar on the Navy Pier, the largest rooftop bar in the country.
• Catch a 1920s burlesque show at Untitled Supper Club.
• Tour the Fulton Street Brewery and Taproom.

Shopping in Chicago

• Shop the Magnificent Mile or Oak Street’s high-end boutiques, luxury brands, and flagship stores.
• Discover unique stores and vintage shops in the charming Andersonville neighborhood.
• Shop the trendy boutiques and eclectic stores in Wicker Park.
• Find a mix of retail, dining, and entertainment on Michigan Avenue at Water Tower Place.
• Buy souvenirs and local products that embody the city’s spirit at Chicago Style.
• Discover eclectic shops and vintage finds in Logan Square.
• Shop for fresh produce and artisanal products in Chicago Farmers Markets.
• Explore department stores and retail chains on State Street.
• Browse through art and crafts from Chicago Riverwalk Art Vendors.
• Discover a variety of shops and dining options at the Shops at North Bridge.
• Explore luxury retailers at 900 North Michigan Shops’ upscale shopping center.
• Experience a historic outdoor market with diverse vendors at Maxwell Street Market.
• Shop for souvenirs in Chinatown Square Mall and Wentworth Avenue in Chinatown.

Instagrammable Places in Chicago: Lookouts, View Points and Selfies

Lookouts and Viewpoints:

• Admire the city from the John Hancock Center’s observation deck, 360 CHICAGO.
• Check out the view from the glass-bottomed Willis Tower Skydeck.
• Ride the Ferris Wheel at Navy Pier.
• Stroll the Adler Planetarium Skyline Walk.

Selfies:

• Snap a selfie at the reflective Cloud Gate in Millennium Park.
• Twirl in front of the iconic Buckingham Fountain in Grant Park.

Photographs:

Wrigley Building, Tribute Tower, the John Hancock Center, Chicago Water Tower, Chicago Theater, Palmer House Hotel, Marshall Field’s (Macy’s on State), the city from the end on Navy Pier and Ohio Street Beach, Crown Fountain in Millennium Park, glass domes at the Chicago Cultural Center, the Great Hall at Union Station, Miro’s Statue, clock on the Old Marshall Field Building.

Special Events

• See the Chicago River turned green during the cities St. Patrick’s Day celebration.
• Lollapalooza four-day music festival held annually in Chicago’s Grant Park.
• View the latest car models and concepts at the Chicago Auto Show.
• Witness thrilling aerial displays over Lake Michigan during the Chicago Air and Water Show.
• Attend the Chicago Blues Festival and celebrate the blues with live performances.
• Enjoy free jazz concerts at Millennium Park during the Chicago Jazz Festival.
• Sample a variety of food from local vendors at Taste of Chicago.
• Attend screenings and panel discussions at the Chicago International Film Festival.
• Join the comic and pop culture celebration during the Chicago Comic & Entertainment Expo (C2E2).
• Attend Chicago SummerDance and dance to live music in Grant Park’s Spirit of Music Garden.

Be Sure to check the Chicago Board of Tourism website for upcoming festivals, special events, and what’s happening this weekend.

Day Trips from Chicago

• Explore the historic town of Galena with preserved 19th-century architecture.
• Spend a day in Milwaukee, Wisconsin exploring museums, breweries, and Lake Michigan.
• Hike through canyons and waterfalls at Starved Rock State Park.
• Relax on sandy beaches with lakefront views at Indiana Dunes National Park.
• Check out the waterfront villages in Door County, Wisconsin.
• Explore Michigan’s Wine Country.
• Ride the dunes in Saugatuck, Michigan.

Plan your Trip to Chicago Illinois

Why Visit Chicago Illinois

Chicago had approximately 49 million visitors last year. People are drawn by beautiful architecture, world-class museums, Broadway theater district, mob history, major league sports, beaches, fun attractions, great shopping, and amazing food. There is truly something for everyone in Chicago

How Many Days in Chicago is Enough

3 days in Chicago is enough to experience the city. Add another day if you plan to attend a special event or wish to take a day trip. BTW, Milwaukee is a short train ride away and a great day trip from Chicago!

Is Chicago Safe for Solo Travelers

According to Travel Safe Abroad, the overall risk of travel in Chicago is medium. Chicago experiences extreme weather, so pay attention to tornado warnings. Chicago is a high target for a terrorist attack and was on the original list of 9/11 targets. Also, Chicago is known for gun violence, carjackings, and gang crimes. As a general guideline, the more dangerous areas are south of I-55 and anywhere north and south of I-290.

The risk of mugging is medium and pickpockets are high. Ask the concierge of the hotel about the safety in the specific area you are staying. Keep your purse close to you and do not walk alone at night. Check their website for more information.

Best Time to Visit Chicago

Chicago experiences all four seasons. Winters are quite cold and summer is hot and humid. The best time to visit Chicago is September through mid-October.

How to Get to Chicago

45 airlines from over 250 cities fly nonstop to the Chicago O’Hare International Airport. A nonstop flight from LAX to Chicago is about 4 hours; JFK to Chicago is 2h 45m. Chicago O’Hare Airport is 45 minutes from the city by Metro Blue Line.

How to Get Around Chicago

Chicago is easy to navigate without a car by “L” The L is the city transportation on elevated tracks. You might also see it called CTA trains or by the color of the line. It’s all the same thing. Purchase a Ventra card for single use, 1-day or 3-day unlimited CTA pass. You can pick up a Ventra card at vending machines for $5 and it’s credited back to your account after you register the card. Check the CTA website for more information. Be sure to download the Ventra App for on-the-go time schedules. Buses, taxis, and Uber also operate in Chicago.

Use the Metra to travel to the Chicago suburbs. The system’s 11 lines extend outward from the Loop, making stops in North, East, and South Chicago before heading on to nearby communities like Evanston, Aurora, Joliet, and University Park.

Where to Stay in Chicago

I recommend staying near the Magnificent Mile, the Loop, or River North. I stayed at the Cambria Hotel in the Loop – Theatre District. It is a mid-priced hotel in a great location.

What Should I Budget for Chicago

According to Budget My Trip, the daily cost of travel is $279 per person per day. As always, the cost is based on your travel style. Check their website for more information.

What Should I Pack for Chicago

Chicago is a casual city. Most tourists wear jeans, shorts, and cotton T-shirts. Be sure to pack comfortable shoes and beachwear if you are traveling during the summer season.

Are There Any Romantic Things to Do in Chicago

Chicago is full of romantic restaurants and great rooftop bars, try The Signature Room at the 95^th. Watching a performance in the Theater District or taking a sunset cruise are great ways to celebrate a special occasion. 

Things to Do in Chicago with Young Children

Families with young children will want to go for a ride on the Ferris Wheel at Navy Pier, stop to play in Maggie Daley Park, visit the Children’s Museum, Legoland, or the Museum of Ice Cream.

Things to do in Chicago with Teens and Young Adults

A Chicago highlight for teens and young adults may be stepping out onto The Ledge of SkyDeck Chicago or TILT at the at John Hancock Center, taking the speedboat tour of Lake Michigan’s waterfront, or visiting the Ice Cream Museum.  Also consider spending time on the beach, watching the free Navy Pier fireworks, watching the digital Art on theMART light show, or wandering the street art on the Wabash Corridor.

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Booking Resources for Chicago Illinois

Chicago Illinois Travel Guide

Pick up an Illinois Travel Guide from Amazon.com to browse on the plane.

Book Your Accommodation in Chicago Illinois Now

Spending the night? Search Booking.com and VRBO in one place to find the perfect property! I recommend staying near the Magnificent Mile, the Loop, or River North. I stayed at the Cambria Hotel in the Loop – Theatre District. It is a mid-priced hotel in a great location.

Chicago Attractions and Day Tours

The best attractions sell out! Don’t chance it, get your tickets now and relax when you arrive.

Travel Essentials

Need a universal travel adaptor, power bank charger, or packing cubes? Save time at my Amazon shop and have travel essentials delivered to your home.

Have a great vacation!