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101+ Things to Do in Chicago

An extensive list of things to do in Chicago for both locals and tourists. This guide to Chicago includes all the best museums, landmarks, annual events, parks, live music venues, shops, and more. It’s all neatly organized so you can find what you are looking for.

101 Things to do in Chicago - all the best museums, parks, annual events, and more!

Things to Do in Chicago:

This list of things to do in Chicago is divided into categories for easy navigation. 

Last updated: March 2022

101 Things to Do in Chicago: The Field Museum
The Field Museum

Chicago Museums

The Field Museum, the Adler Planetarium, and the Shedd Aquarium are all located on Museum Campus.

The Field Museum

Chicago’s famous T-Rex, Sue, can be found at this natural history museum along with cultural collections and anthropological artifacts from all over the globe.

Adler Planetarium

This was America’s first planetarium, and it’s the place to learn about astronomy and astrophysics.

The Shedd Aquarium

Chicago’s aquarium is home to a wide range of animals including dolphins, penguins, sharks, sea otters, and more. If you visit in the summer, you might want to plan your visit around the Jazzin’ at the Shedd outdoor concert series. 

Museum of Science and Industry

It’s easy to spend a full day in this massive museum with exhibits about space travel, farming, and transportation. While the museum is geared towards children, adults like to see the German U-boat.

The Art Institute of Chicago

This is Chicago’s largest art museum. It is known for its collection of Impressionist and Modern works and hosts several special exhibitions each year.

The Museum of Contemporary Art

A museum that showcases contemporary painting, sculpture, installations, and performances. The MCA has a permanent collection and hosts blockbuster traveling exhibits. 

Chicago History Museum

The Chicago History Museum has a great mix of exhibits for children and adults. See dioramas of the city before the Great Fire, learn about Lincoln, see Chicago artifacts like L car number 1, or view a special exhibit.

The Lincoln Park Zoo

Located within Lincoln Park, this free zoo has a wide range of animals including giraffes, zebras, lions, snakes, and flamingos. In December, the zoo is lit up with thousands of light displays for Zoolights.

Peggy Notebaert Nature Museum

The nature museum is geared towards children and has exhibits to learn about Chicago’s environment, wildlife, and nature. There is also a toddler playspace and a butterfly garden.

Chicago Children’s Museum

The perfect place to go with kids on a rainy or cold day, this museum has a variety of playspaces and a dinosaur exhibit.

National Museum of Mexican Art

Learn about Mexican art and culture at this Pilsen museum.

DuSable Museum of African American History

African American history, culture, and art are the focus of this museum in Hyde Park.

Best Things to Do in Chicago: Chicago Landmarks - Cloud Gate

Chicago Landmarks

Chicago’s most iconic architectural and historic landmarks.

Cloud Gate

Often referred to as “the bean”, the Cloud Gate sculpture is one of the most recognizable symbols of Chicago.

The Sears Tower

They say that Chicago didn’t have any mountains so we built our own in the form of the skyscrapers that create the skyline. Formerly called the Sears Tower, but now called the Willis Tower, it was the tallest building in Chicago when it was built in 1973. There is a tour available that takes visitors to the top to take in the expansive view.

Wrigley Field

The Cubs home is one of the oldest and most beautiful baseball stadiums in America. If you don’t feel like catching a game, you could go on a tour or to a concert.

Buckingham Fountain

This Rococo-style fountain is located in the center of Grant Park and is one of the largest fountains in the world. The fountain operates from April to October and has water shows every hour on the hour during the day and colored light shows at night.

Historic Water Tower

This beautiful water tower on the Magnificent Mile survived the Great Chicago Fire of 1871.

Navy Pier

Navy Pier is a hub of entertainment and activities located on a large pier along Lake Michigan. Many boat tours and bike tours leave from Navy Pier, plus it is home to many restaurants, a Ferris Wheel, a carousel, and the children’s museum. On Wednesdays and Saturdays during the summers, fireworks can be seen from the pier.

The Riverwalk

The Riverwalk is a path along the south side of the Chicago River where you can take in views of the city’s architecture including the bridges, the Wrigley Building, and Marina Towers. The Riverwalk is home to a few bars and restaurants including City Winery.

Calder’s Flamingo

You can find this large brilliant red steel Alexander Calder sculpture in Federal Plaza in Chicago’s Loop.

Robie House

The father of Prairie School Architecture, Frank Lloyd Wright, designed this home in Hyde Park. Tours are available.

Best Things to do in Chicago - set sail on Lake Michigan

Best Things to Do in Chicago

Get out and explore!

Bike Along the Lakefront

The Lakefront Trail is an 18-mile biking and pedestrian path alongside the lake and the beaches. Bike rental is available at North Avenue Beach, and there are several Divvy Stations near the lakefront.

Green City Market

Chicago’s biggest farmers market has three locations. The original (and biggest) is in Lincoln Park on Wednesdays and Sundays. There are additional locations at Gallagher Way in Lakeview and in the West Loop. The market takes place outdoors from May through October and moves inside for the colder months. Vendors sell produce, flowers, cheese, baked goods, and more.

Watch the Navy Pier Fireworks

Fireworks are launched from near Navy Pier every Wednesday and Saturday from Memorial Day to Labor Day. Several companies offer boat cruises providing guests with views of the fireworks against the Chicago skyline.

Bloomingdale Trail (the 606)

An elevated path for walkers, runners, and bikers that runs along the border of Wicker Park and Bucktown.

Music Box Theatre

See art-house and independent films at this two-screen cinema in Lakeview.

Chicago Magic Lounge

The magic lounge in Andersonville has a bar, live music, and magic shows for families and adults.

Randolph Street Market

This vintage and antique market takes place the last weekend of the month during the summer and features acres of shopping, food, and live music.

Things to Do in Chicago - Tours of Chicago

Tours of Chicago

Chicago has architecture tours, bike tours, food tours, walking tours, gangster tours, and more!

Architectural Boat Tour

The Chicago Architecture Foundation Center’s Architectural Boat Tour usually tops lists of things to do in Chicago. The tour takes you on a cruise down the Chicago River past many of Chicago’s iconic skyscrapers – it is a fun way to learn about architecture and Chicago’s history.

Bobby’s Bike Hike

This tour company offers bike tours, walking tours, and food tours.

Chicago Food Planet’s Food Tours

You can opt for neighborhood-specific or cuisine-specific walking tours with Chicago Food Planet.

Free Walking Tours with Chicago Greeters

Chicago Greeters hosts free two-hour and four-hour walking tours – the only requirement is that you register at least ten days in advance.

Chicago Pizza Tours

Travel to different neighborhoods to taste pizzas from 3-4 independently-owned pizzerias.

Chicago Prohibition Tour

This company offers tours taking guests to former speakeasy via bus, and they offer cocktail workshops.

Tall Ship Windy

Set sail on Lake Michigan on a schooner! Tall Ship Windy has a few different tour options including a fireworks cruise and a pirates pub sails.

Chicago Crime Tours

Visit infamous crime scenes and learn about notorious mobsters. The tour company has a variety of tour options.

Untouchable Tours

Go on a Gangster Tour led by actors that take on the personas of infamous Chicago gangsters.

Chicago History Museum Tours

In addition to offering tours through the museum itself, the Chicago History Museum offers neighborhood walking tours.

Loop Interior Architecture

The focus of this tour is interior architecture, taking guests into the lobbies of some of Chicago’s architectural gems. The tour includes the (easy to get lost in) underground Pedway system.

Chicago Parks and Beaches

Chicago has 28 miles of beaches and lots of parks to explore.

Maggie Daley Park

Maggie Daley Park is a collection of playgrounds for children of all ages plus a skating ribbon and rock climbing wall.

North Avenue Beach

This popular beach is a hub of summertime activities including volleyball, stand-up paddle-boarding, kayaking, biking, and jet skiing. This beach has a large boat-shaped bar/restaurant and access to the Lakefront Trail.

Ohio Street Beach

This beach is just beside the skyline, located between the Gold Coast and Streeterville. There is a cafe and some volleyball courts at Ohio Street Beach.

Montrose Beach

For a less crowded beach, head to Montrose Beach in Uptown. This beach has volleyball courts and kayak rentals and a quieter vibe than North Avenue Beach.

Grant Park

A grand park that is home to the Buckingham Fountain and many gardens, athletic fields, and tennis courts. Events such as Lollapalooza and the Taste of Chicago take place here.

Millennium Park

This park is home to Cloud Gate. Just behind Cloud Gate, there is a large green field and amphitheater that hosts concerts and Chicago Gourmet.

Gallagher Way

Located between Wrigley Field and Hotel Zachary in Lakeview, this park hosts the Green City Farmer’s Market, concerts, movie nights, kid’s activities, fitness events, and a Christkindlmarket in December.

Lincoln Park

Chicago’s largest park is home to the nature museum, the Lincoln Park Conservatory, the zoo, and the Green City Farmers Market. There are sports fields, gardens, and plenty of green space for picnicking.

Garfield Park Conservatory

Located within Garfield Park, this botanical conservatory has several indoor and outdoor gardens. It is free to the public and open all year.

Lincoln Park Conservatory

This conservatory and botanical garden is where thousands of flowers and plants are grown to be planted with Lincoln Park. It is open all year and entrance is free.

Best Annual Events in Chicago

Chicago’s best annual and seasonal events.

Renegade Craft Fair

This massive fair is filled with local makers who sell everything from clothing to marshmallows. It’s coming to Chicago four times in 2022!

Chicago Blues Festival

A June festival that takes place in Millennium park and features live blues bands.

Chicago Jazz Festival 

A free festival that takes place on Labor Day Weekend.

Chicago Gourmet

A weekend-long event showcasing some of Chicago’s best restaurants. Guests can try bites from dozens of restaurants, taste wines, and watch cooking demonstrations from well known chefs.

Taste of Chicago

A large festival with food, drinks, and live music that takes place in Grant Park each July.

The Air and Water Show

A mid-July event that takes place on the Chicago lakefront. The most popular event of the weekend is the formation jet flyers.

St. Patrick’s Day

Chicago goes big for St. Patrick’s Day. The essential St. Patrick’s Day event is the Chicago River being dyed green the Saturday before March 17th (on the 17th if it happens to be a Saturday. Once the river is green, celebrations and parades take place all over the city.

Pride Parade

The Pride Parade is a massive celebration that takes place in Boystown each June.

Millennium Park Music Series

A free summertime music series that takes place outside at the Millennium Park amphitheater.

Old Town Art Fair/Wells Street Art Festival

It is easy to get these two festivals confused, or to think that they are the same event since the take place at the same time on nearby streets in Old Town. The Art Fair is focused on art and the Art Festival is a street festival with bands and more food and drink options.

Bike the Drive

An annual event in May in which Lakeshore Drive is closed to traffic and opened for cyclists.

Sheffield Music Festival and Garden Walk

This events combines garden tours and a street fest with live music, food, and drinks.

Northalsted Market Days

A street fest that caters to the LGBTQ+ community that is known having a fun party atmosphere. 


In recent years this European-style Christmas market has expanded to have locations at Daley Plaza and Gallagher Way. The markets have vendors serving mulled wine, spiked hot chocolate, and a variety of other food and drinks. There are also craftspeople selling holiday ornaments and gifts. 

Zoo Lights

An annual event during the holiday season, Zoo Lights takes place at the Lincoln Park Zoo and involves elaborate light decorations and light shows.

Sports Teams

There are professional baseball, football, soccer, basketball, and hockey teams in Chicago.

The Blackhawks

Chicago Blackhawks games are fun even if you don’t love hockey. If you need to pick between seeing the Bulls and the Blackhawks, pick the Blackhawks – the games are lively events filled with Chicago pride. Both the Blackhawks and the Bulls play at the United Center in the West Loop.

The Bulls

Chicago’s basketball team plays at the United Center and games are very family-friendly.

The Cubs

Seeing a game a Wrigley and singing Go Cubs Go (assuming they win) is a true Chicago experience. Ticket prices and availability can depend on the team’s performance and the time of year. If you want a rowdy time, get bleacher tickets. If you want to stay dry no matter the weather, many of the seats do have coverage from the weather. If you go in April, be warned that temperatures may be frigid.

The White Sox

While the Cubs play on the North Side in stadium over 100 years old, the White Sox play in a much newer stadium on the South Side.

The Bears

The Bears play at Soldier Field. If you decide to go to a game, be aware that the stadium doesn’t have roof and it can get very cold in the late fall and winter. (So cold your beer freezes).

The Chicago Fire

Chicago’s Major League Soccer team also plays at Soldier Field. 

Music Festivals

A guide to Chicago’s big music festivals.


A massive four-day eight-stage summer music festival featuring over 170 bands. Artists including Paul McCartney, Arcade Fire, the Red Hot Chili Peppers, Lady Gaga, Foo Fighters, Journey, Florence and the Machine, and Metallica have headlined Lollapalooza in recent years.

Windy City Smokeout

Smokeout is the combination of a country music festival and a food festival. It takes place over four days in July and features pit masters from all over the country. Headliners for 2022 include Tim McGraw, Miranda Lambert, and Willie Nelson.

Riot Fest

This September fest and features rock, alternative, and punk music and attracts an Gen-X crowd.


This three-day July festival has a wide range of artists and more emerging acts. 

North Coast Music Festival

A three-day festival that takes place on Northerly Island over Labor Day weekend. In addition to bands, the event features installation art.

Pop Up Beer Dinner with Lakeshore Beverage and Whole Foods

Chicago Breweries

Chicago is home to over 160 breweries, more than any other city in the country.

Revolution Brewing

Revolution has two locations in Chicago. There is a brewery and taproom in Avondale that offers tours and there is a taproom and restaurant in Logan Square.

Goose Island

Goose Island’s Brewhouse on Clybourn has a taproom, restaurant, and brewery tours. There is also a taproom located in the West Loop.

Half Acre

Half Acre has a taproom and beer garden Balmoral Avenue.


Lagunitas has a production facility, taproom, and restaurant in the Pilsen neighborhood.

Ravinia Brewing

A brewery and restaurant in Avondale that serves Mexican fare.

Off Color Brewing

Off Color has a taproom called The Mousetrap in Lincoln Park serving beer and cocktails. They don’t have a kitchen but guests are welcome BYO food.

Metropolitan Brewing

Metropolitan has a brewery/taproom in Avondale that is open daily. The space doesn’t have a kitchen but guests are welcome to BYO food.

Live Music in Chicago

These bars and restaurants are known for having live music on a regular basis.

Phyllis’s Musical Inn

A cash only bar in Wicker Park that has been around since the 1950s. It is known for hosting an eclectic mix of bands. Usually you can find jazz on the calendar once or twice a week.

The Green Mill

Chicago’s essential jazz bar was also a favorite hangout for Al Capone. Like most bars on this list, be prepared to pay a cover.

Kingston Mines

A blues bar in Lincoln Park with two stages and live music seven nights a week. Buy tickets at the door.


Also in Lincoln Park and very close to Kingston Mines, B.L.U.E.S. is a bar with nightly live blues music.

The Hideout

The Hideout in Bucktown hosts live music and dancing on Saturdays.

Andy’s Jazz Club & Restaurant

A jazz lounge in River North with nightly live music.

Bub City

A popular barbecue restaurant that hosts live music karaoke once a week in addition to country music bands.

Buddy Guy’s Legends 

Owned by Buddy Guy, who sometimes graces the stage, this blues club in the loop has live music every night.

Concert Venues in Chicago

Chicago has music venues sprinkled throughout the city.

The Chicago Theater

This theater in the Loop hosts a mix of concerts, comedians, and other events.

Thalia Hall

Located in a landmark building in Pilsen, this intimate venue hosts concerts, but there are some comedians and other shows on the calendar too. It shares a building with a bar and a restaurant.

The Vic

A Lakeview theater that hosts indie artists, mid-sized concerts, and movie nights.

The Aragon Ballroom

A large Uptown venue with room for 5,000 people. It is one of the bigger “small venues” when you compare it against the stadiums and the other spots on this list.

The Riviera

Located across the street from The Aragon, The Riviera is smaller with a capacity of 2,500 people.

Park West

Park West opened in 1916 as a vaudeville and movie theater and today it is a 1,000 guest concert venue. The venue is big enough to get some great bands (think Trombone Shorty and Ingrid Michelson) but small enough to feel like you have been let in on a secret.

Schubas Tavern

Located in an old Schlitz brewery in Lakeview, Schubas is the place to see indie acts, comedy, jazz, and more.

Lincoln Hall

Located in Lincoln Park, Lincoln Hall is a midsized concert venue with a bar and a restaurant.

City Winery

A winery, restaurant, and small concert space in the West Loop. Their calendar is packed with events nearly every night.

House of Blues

The House of Blues in the Loop just behind the Marina Towers and hosts a variety of musicians.

Empty Bottle

A bar and music venue known for showcasing indie and alternative bands in Ukrainian Village.


An intimate concert venue just north of Wrigley Field that is popular with indie and alternative bands.


A venue just off the Blue Line in Wicker Park that hosts a wide range of concerts and events.

Bottom Lounge

A West Loop spot where you can see underground music.

United Center/Soldier Field/Wrigley Field

The largest concerts in Chicago take place at these stadium venues. The United Center is indoors and has shows all year, while Soldier Field and Wrigley Field are outdoor venues used in warmer months.

Chicago Theater, Opera, and Dance

These are the places to see musical theater, plays, operas, and dance performances.

Broadway in Chicago

There are several theaters in the Loop that host traveling Broadway productions as well as locally produced shows.

Steppenwolf Theatre

This three-stage theatre company in Lincoln Park is known for developing new plays and has won 12 Tony Awards. The theatre company produces up to 16 plays each year.

Lookingglass Theatre

Founded in 1988 by Northwestern University graduates, the Lookingglass Theatre showcases new plays.

Chicago Shakespeare Theatre

Don’t let the name fool you, this Navy Pier theater stages more than Shakespeare. In 2022 it will host the world premiere of The Notebook musical.

Hubbard Street Dance

This famed contemporary dance company performs at the Harris Theater in Millennium Park.

Lyric Opera

The opera house is in the loop and puts on about 9 operas each season.

Joffrey Ballet

The Joffrey Ballet is Chicago’s home for classical and contemporary ballet. They perform at the Lyric Opera and the company is known for their annual production of The Nutcracker.

Comedy Clubs in Chicago

Chicago is home to world-famous comedy theaters and small neighborhood venues, here are some of the best places to see comedy in Chicago.

Second City

Second City is an improv theater and school in Old Town where many SNL cast members got their start. The theater has multiple stages and shows, purchase tickets in advance since shows sell out.


Located down the street from Second City in Old Town, Zanies hosts well-known stand-up comics. Notes that the venue is 21+ only.

iO Theater

Tina Fey, Amy Poehler and Stephen Colbert all trained at this Lincoln Park improv theater. It sold in 2021 and reports say that it will reopen.

The Comedy Bar

This standup comedy venue has two stages and is located within Gino’s East Pizzeria. The Comedy Bar hosts comics, open mics, and ensemble shows.

Laugh Factory

This Lakeview comedy club hosts famous standup comedians and hosts showcases of emerging comedians.

CSz Theater Chicago

CSz stands for Comedy Sports and this improv troop treats comedy like a sport in which two improv teams compete for applause. They perform at The Den in Wicker Park.

The Annoyance Theatre

A two-stage theater and improv school located in Lakeview East. The calendar features a mix of improv, sketch comedy, stand up, musicals, and plays. 

Shopping in Chicago

The Magnificent Mile

This mile-long stretch of Michigan Avenue connecting Streeterville and the Gold Coast is the place for upscale shopping. Stores along the mile include Neiman Marcus, Apple, Saks, Burberry, Tiffany & Co., and Gucci. The 900 North Michigan Shops, the Shops at North Bridge, and Water Tower Place are all located along the Mag Mile.

900 North Michigan Shops

Home to Bloomingdales, JCrew, Bonobos, Gucci, Pyscho Bunny and more. Don’t miss Aster Hall, a beautiful food hall and a wonderful menu.

The Shops at North Bridge

Nordstrom and Eataly anchor this urban mall.

Water Tower Place

When compared to the 900 North Michigan Shops and the Shops at North Bridge, the retailers that this mall are a bit more affordable. The Macy’s is set to close soon. The prime attraction here is the American Girl Store.

Block 37

A shopping center in the Loop with shops like Anthropologie, Zara, Banana Republic, Sephora, The Disney Store, Magnolia Bakery, and more. The food hall, Latinicity is not to be missed.

Fashion Outlets of Chicago

A luxury fashion outlet with stores including Bloomingdales, Burberry, Gucci, JCrew, Lululemon, Neiman Marcus, Prada, and Saks Off Fifth located by O’Hare in Rosemont.

The Gold Coast

The Magnificent Mile ends in the Gold Coast and the 900 North Michigan Shops are in this neighborhood. Luxury retailers like Dior, Hermes, and Prada have flagship stores here.

Lincoln Park

Shoppers will find a mix of locally owned boutiques and familiar names along Armitage and Halsted Streets.

Wicker Park

Wicker Park has lots of sneaker shops, record stores, and vintage boutiques plus shops like Free People, Urban Outfitters, Lululemon, and Levis.


If you want to check out independently owned shops and antiques stores, head to Andersonville.