This list of 200+ things to do in Chicago includes all the best museums landmarks, annual events, parks, bars, restaurants, live music venues, shops, and more. It’s all neatly organized so you can find what you are looking for.
I have lived in Chicago for the past 11 years and I am excited to share my guide of the best things to do in Chicago. This guide is for both tourists and locals – no matter what you will find something fun to do.
200+ Things to Do in Chicago:
I have divided this list of things to do in Chicago into categories to make it easier to navigate.
This list was written in April 2020 with the goal of creating a long term resource. Many of the events mentioned in this list may be cancelled for 2020.
Chicago Museums
Chicago’s largest art museum has a large collection of Impressionist and Modern works and hosts several special exhibitions each year.
This natural history museum is home to Sue the T-Rex plus anthropological collections and cultural artifacts from around the world.
Chicago’s aquarium is home to a wide range of animals including dolphins, penguins, sharks, sea otters, and more. In the summer, the aquarium hosts Jazzin’ at the Shedd, a jazz concert on their terrace overlooking Lake Michigan.
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.
Learn about the history of Chicago at this museum on the border of Old Town and Lincoln Park. I’ve been many times and am always impressed by the special exhibitions that touch on fashion, local history, unusual objects, and more.
The Adler Planetarium was the first planetarium in America and is dedicated to the study of astronomy and astrophysics.
Museum of Science and Industry
Explore one of just four surviving German U-boats at this massive museum geared towards children. Other exhibits tackle topics like Tesla coils, tornados, boats, and robots.
This free zoo is located within Lincoln Park. See lions, tigers, bears, giraffes, monkeys and more here.
Also located within Lincoln Park, this nature museum has a butterfly haven and specimens of a wide variety of animals.
Located on Navy Pier, this museum has educational play spaces for children of all ages plus a kid’s town, an art studio, a dinosaur exhibit, and a tinkering lab.
National Museum of Mexican Art
This museum in Pilsen showcases 3,000 years of Mexican art and culture.
DuSable Museum of African American History
A museum in Hyde Park dedicated to the study and conversation of African American history, culture, and art.
Chicago Landmarks
These are some of Chicago’s most famed landmarks!
Cloud Gate (The Bean)
This sculpture is located within Millennium Park and is one of the most recognizable symbols of Chicago.
Wrigley Field
The home of the Cub’s is probably the most beautiful ball park in America. It’s also the second oldest. Go for a game, a tour, or a concert.
Navy Pier
Navy Pier is a large pier that goes out into Lake Michigan. It is home to many restaurants and a giant Ferris Wheel. During the summer fireworks can be viewed from the pier on Wednesdays and Saturdays.
Historic Water Tower
Located along the Magnificent Mile the Historic Water Tower is a architecturally beautiful water tower that was built in 1869 and survived the Great Chicago Fire or 1871.
Willis Tower (Sears Tower)
When construction was completed in 1973 it was the tallest building in the world. It remains the tallest building in Chicago. The Skydeck is an observation deck that provides views of four states on a clear day.
The Riverwalk
The Riverwalk runs along the south side of the Chicago River and will give you views of some of the city’s most iconic architecture including Marina Towers and the Wrigley Building.
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.
Calder’s Flamingo
This large and colorful abstract sculpture can be found in Federal Plaza.
Robie House
This Frank Lloyd Wright house in Hyde Park is a prime example of Prairie School Architecture.
Best Things to Do in Chicago
Here are some of my favorite things to do in Chicago. These are can’t miss activities and events that didn’t quite fit anywhere else on this list.
Bike Along the Lakefront
Chicago has 28 miles of beach along Lake Michigan and the Lakefront Trail is an 18-mile biking and pedestrian path alongside the lake. You can get a bike share bike (Divvy Bike) or rent a bike at North Avenue Beach.
See the Fireworks
Chicago celebrates summer with fireworks shows every Wednesday and Saturday from Memorial Day to Labor Day. The fireworks are launched near Navy Pier and some of the best places to view them are from Navy Pier, from a fireworks cruise, and from Cindy’s Rooftop.
This is Chicago’s most beloved farmers market. It takes place on Wednesdays and Saturdays from May through October in Lincoln Park. Vendors sell flowers, prepared foods, produce, grocery items, baked goods, and more. There are also Green City Market locations at Gallagher Way beside Wrigley Field and in the West Loop.
Randolph Street Market
This vintage and antiques market takes place the last weekend of the month during the summer and features eight acres of shopping, seating, drinking, and live music.
Bloomingdale Trail (the 606)
This is an elevated pedestrian path that runs along the north edge of Wicker Park.
A two screen cinema on Lakeview’s Southport Corridor that shows art house and independent films. The theater is also known for hosting unique special events.
Centennial Wheel
This massive Ferris wheel is located on Navy Pier.
Located in Andersonville, the magic lounge has a bar, live music, and magic shows. They also have family-friendly shows.
Tours of Chicago
Chicago has architecture tours, bike tours, food tours, walking tours, gangster tours, and more!
Architectural Boat Tour
This is hugely popular is considered one of the best things to do in Chicago for good reason. The tour combines Chicago history and architecture with a cruise down the river on a boat that has a bar. There are several different companies that offer this tour but the best is hosted by the Chicago Architecture Foundation Center on the boat named the Chicago’s First Lady.
Bobby’s Bike Hike
One of the city’s top tour operators, Bobby’s Bike Hike has bike tours as well as food tours and walking tours too.
Chicago Food Planet’s Best in Chow Food Tour
This food tour highlights the foods that Chicago is famous for: deep-dish pizza, hot dogs, Italian beef sandwiches, popcorn, and more.
Free Walking Tours with Chicago Greeters
Join a free 2 hour or 4 hour walking tour led by Chicago Greeters. Just make sure to register at least 10 days in advance.
Chicago Pizza Tours
Guests visit 3 independent neighborhood pizzerias during this tour.
Chicago Prohibition Tour
Visit four former speakeasies via bus on this tour.
Tall Ship Windy
Board a four-masted schooner and set sail on Lake Michigan for this tour.
Chicago Crime Tours
This tour takes you through different Chicago neighborhoods and to the site of the St. Valentine’s Day Massacre. The tour company has a variety of tour options.
Chicago Gangster Tour
Run by Untouchable Tours, this tour involves tour guides that take on the personas of infamous Chicago gangsters.
Chicago History Museum Tours
The museum offers a variety of Chicago tours including a Devil in the White City tour.
Loop Interior Architecture
Many tours focus on Chicago’s remarkable architecture, but this one focuses on interior architecture. Go inside some of the city’s most famous buildings and explore the underground Pedway system on this tour.
Chicago Parks and Beaches
Yes, Chicago has over 20 miles of beaches along Lake Michigan. The city also has some beautiful parks to explore.
North Avenue Beach
Probably Chicago’s most popular beach, North Avenue Beach is beside Lincoln Park. Bike, stand up paddle board, kayak, and jet ski rentals are available at this beach. Plus there are dozens of volleyball courts, access to the Lakefront Trail, and a large (often rowdy) bar/restaurant called Castaways.
Ohio Street Beach
A beach located between Streeterville and the Gold Coast with skyline views, volleyball courts, and a cafe.
Montrose Beach
This Uptown beach isn’t as crowded as the beaches closer to downtown. This beach has volleyball courts and kayak rentals.
Grant Park
A massive park in downtown Chicago that hosts events like Lollapalooza and the Taste of Chicago. The park contains gardens, athletic fields, tennis courts, and borders the Art Institute and Museum Campus.
Millenium Park
This park located beside Grant Park hosts free movies and concerts in the summer and events like Chicago Gourmet.
Maggie Daley Park
A paradise for children, this park has a variety of playgrounds for children of different ages, and an ice skating ribbon.
Lincoln Park
This is Chicago’s largest park. It’s home to the zoo, the nature museum, the Lincoln Park Conservatory, and a farmers market. It also has acres of green space and athletic fields.
Lincoln Park Conservatory
Located within Lincoln Park, this conservatory and botanical garden is free and open year-round. Its mission is to showcase exotic plans and to grow the thousands of plants needed for the park.
A botanical conservatory located within Garfield Park that is free to the public and open all year. It has several indoor gardens and outdoor gardens.
Gallagher Way
This small park beside Wrigley Field hosts concerts, movie nights, and a farmers market.
Chicago Sports Teams
Chicago has baseball, football, soccer, basketball, and hockey teams.
The Cubs
The lovable losers turned 2016 World Series Champions play at Wrigley Field on the North Side of the city. Ticket availability can depend on how well the team is doing and the time of year.
The White Sox
The White Sox play on the South Side and their stadium has some pretty good food options.
The Bears
Our football team plays at Soldier Field and tailgating is a popular activity in the parking lot before games.
The Chicago Fire
Chicago’s Major League Soccer team also plays at Soldier Field.
The Bulls
These aren’t your 1990s Bulls. They… aren’t that great. Expect no fewer that 3 dance teams to perform throughout the game. Why? I don’t know. The bulls play at the United Center.
The Blackhawks
Chicago Blackhawks games are bursting with Chicago pride. In the past decade, our hockey team is our winningest sports team. The Blackhawks play at United Center in the West Loop.
Best Annual Events in Chicago
Chicago hosts hundreds to festivals and annual events – here are my picks:
Chicago Blues Festival
A free live music festival that takes place in Millennium Park each June.
Chicago Jazz Festival
A free festival featuring jazz music that takes place over Labor Day weekend.
Chicago Gourmet
A food and wine centric event that takes place at the end of September where guests try samples of food from Chicago restaurants. Buy tickets in advance since this event can sell out.
Taste of Chicago
A large food festival that takes place in Grant Park each July. In addition to food vendors, this festival also has live music.
The Air and Water Show
A weekend-long event that takes place in mid-August and involves jets loudly flying around.
St. Patrick’s Day
St. Patrick’s Day is a big deal in Chicago. The Saturday before March 17th (or on March 17th if it falls on a Saturday) the festivities kick off with the Chicago River being dyed green. There are parades, street parties, and lots of people bar-hopping.
Pride Parade
The Pride Parade takes place at the end of June. This is a huge celebration that draws a very large crowd to Boystown.
Christkindlmarket
A European-style Christmas market takes over Daley Plaza from the end of November through December.
Zoo Lights
The Lincoln Park Zoo dresses up for the holidays with a massive light show – the best part is that admission to the zoo is free.
Millennium Park Music Series
This series of free concerts takes place between June and August.
Old Town Art Fair/Wells Street Art Festival
This pair of street fests take place on the same weekend in June. The Art Fair is very art focused while the Art Festival is a big street festival with live music.
An annual event that takes place in May where Lakeshore Drive is closed so that people can bike the drive.
Sheffield Music Festival and Garden Walk
Part street fest with live music and food/drink vendors and part garden tour, this festival takes place in July.
Northalsted Market Days
A rowdy street festival with food, drinks, and entertainment that caters to the LGBTQ+ community.
Music Festivals in Chicago
Chicago has lots of music festivals – this list includes the bigger ones.
This is Chicago’s biggest music festival. It takes place over 4 days at the start of August and features 8 stages and over 170 bands. I’ve seen bands and artists like Paul McCartney, Green Day, Lady Gaga, Arcade Fire, The Alabama Shakes, James Bay, and Snoop Dogg play this festival.
This 3 day festival takes place in July and I think of it as Lolla’s cool little sibling. Pitchfork has a wider range of artists and more emerging acts.
A 3 day festival devoted to country music and barbecue. Even if you aren’t into country music, the food is exceptional with pit masters from all over the country joining in the fun.
If Pitchfork is Lolla’s younger sibling, Riot Fest is its Gen X older sibling. This festival takes place in September and features rock, alternative, and punk music.
A 3 day festival that takes place on Northerly Island in September and features a variety of bands plus performance and installation artists.
Chicago’s Best Restaurants
This list includes the best of the best Chicago restaurants. These are restaurants that I have been to and loved; luckily in Chicago there is no shortage of exceptional places to eat.
Bavette’s Steakhouse & Bar
A beautiful and romantic candlelit restaurant in River North that specializes in steak. It’s one of the best meals you can have in Chicago.
Alinea
Alinea is Chicago’s only restaurant with 3 Michelin stars. It’s known for its sophisticated atmosphere and cuisine which often experiments with molecular gastronomy. Reservations are necessary.
Roister
A casual sister restaurant to Alinea, and one of our favorite places to dine in Chicago, Roister proves that you can have top notch food in an approachable space. I love the chicken three ways, which is one of their classic menu items.
Next
Another sister restaurant to Alinea, Next has received twenty-one 4-star reviews from the Chicago Tribune and is known for it’s multi-course menu that changes to fit a theme. If you want to dine at Next, plan ahead, it books up far in advance.
Avec
Avec brings together a rustic casual atmosphere and exceptional Mediterranean influenced food. They serve both small plates and larger plates for sharing and the chorizo stuffed dates are a must order item.
Girl and the Goat
Top Chef winner Stephanie Izard’s restaurant has a family style menu the showcases the chef’s creativity. Be sure to try the goat!
Little Goat Diner
A diner that serves breakfast all day plus sandwiches and dinner options. The menu has a mix of diner staples, Southern classics, and global cuisine.
Duck Duck Goat
A sister restaurant to Girl and the Goat and Little Goat that serves Dim Sum and Chinese cuisine.
Au Cheval
An upscale diner in the West Loop that is famous for having one of the best burgers in America. They don’t take reservations and I have seen the wait for a table be up to 5 hours long.
The Publican
A pork and seafood focused restaurant with beer hall decor. The Publican also has one of the best man-friendly brunches in Chicago.
Monteverde
Sarah Grueneberg’s James Beard Award winning restaurant in the West Loop is known for house-made pastas.
Osteria Langhe
A restaurant that serves exquisite cuisine from the Piedmont region of Italy.
Gibsons
One of Chicago’s most well-known steakhouses, this is the place for the classic steakhouse experience: seafood towers, wedge salads, steaks, potato sides, and giant shareable desserts.
Gibsons Italia
A large three level restaurant beside the Chicago River that serves steaks and pastas.
3 Arts Club Cafe
A beautiful restaurant located in the atrium of the Gold Coast Restoration Hardware that serves American cuisine and one of my favorite brunches.
Big Star
This massively popular taco joint has locations in Wicker Park and Wrigleyville. It’s a casual spot for margaritas, guacamole, and tacos. The sunny patio of their Wicker Park location is the place to be on a warm day.
Dove’s Luncheonette
A Tex-Mex diner in Wicker with counter service and menu items like burnt ends hash, fried chicken, and chile relleno.
The Bristol
An American restaurant that serves house-made pasta in addition to perfectly roasted meats.
Mindy’s HotChocolate
A restaurant owned by Mindy Segal, a James Beard Award winning pastry chef, that serves lunch, dinner, and brunch. They also sell a grab and go pick up menu on Fridays, Saturdays, and Sundays featuring both sweet and savory pastries.
The Purple Pig
A Mediterranean small plates restaurant known for serving cheese, wine, and swine. It’s a restaurant that accommodates groups very well.
Bub City
A bbq joint that serves slow cooked meats and classic Southern sides. They have a busy live music schedule that includes weekly live band karaoke.
RPM Italian
A chic Italian restaurant serving both classic Italian pasta dishes and more modern creations.
RPM Seafood
A newly opened multi-level restaurant with views of the Chicago River. Seafood is the star of the show here, but they also serve pasta and meat mains.
RPM Steak
An upscale steakhouse that serves nearly two dozen different cuts of beef including luxury cuts like Wagyu and Kobe.
Mercat a la Planxa
A Spanish restaurant across from Grant Park owned by Iron Chef Jose Garces that serves small plates and paella.
Frontera Grill
Owned by Rick Bayless, Frontera Grill serves authentic Mexican cuisine made with locally sourced ingredients.
Bar Siena
Owned by Top Chef winner Fabio Viviani, this is a casual bar/restaurant serving Italian food including pizzas, pastas, and antipasti. They serve lunch and dinner, plus an excellent weekend brunch.
Beatnik on the River
A beautiful restaurant on the Chicago River serving global cuisine and tropical cocktails.
Summer House Santa Monica
A sunny restaurant with a California-inspired menu featuring tacos, salads, steaks, and more. They also have a drool inducing pastry counter.
Mon Ami Gabi
A classic French restaurant and ideal spot for a date.
Blue Door Kitchen/Blue Door Farmstand
A pair of restaurants owned by Art Smith who was Oprah’s chef for some time. Blue Door Kitchen is a bit more formal than Farmstand which is a casual cafe. Kitchen is known for their fried chicken, and Farmstand has a brussels sprout and kale salad with a cult following.
Cafe Ba Ba Reeba
A Spanish tapas restaurant in Lincoln Park where you can sip sangria and dine on paella and small plates. I love the patatas bravas and the beef tenderloin topped with blue cheese.
Athenian Room
My favorite spot for Greek food – I love the crispy juicy Kalamata Chicken that comes on a bed of fries.
Pequod’s Pizza
This is Chicagoan’s favorite place to get deep dish pizza. Pequod’s is known for their parmesan crust which sets it apart from all the other deep dish spots.
Sweet Mandy B’s
A darling bakery in Lincoln Park that serves cupcakes, cakes, cookies, bars, and other sweet treats.
Club Lucky
An old school red sauce Italian place with a large menu and a killer meatball salad.
Piece Brewery & Pizza
Our go-to spot for pizza serves New Haven style pizzas, not deep dish. This spot has a great selection of toppings and never disappoints.
Pub Royale
This restaurant takes its inspiration from the London pubs that serve Indian cuisine. It’s a great place to dine with friends, and in addition to Indian curries they have a top-notch burger and excellent cocktails.
Schwa
Dinning at Schwa is a culinary experience you will never forget. The small restaurant serves a multi-course menu of innovative American cuisine.
etta
A restaurant in Wicker Park serving a mix of Italian and American food including steaks, pizzas, and pastas.
Somerset
Our go-to date night spot! Somerset has both outstanding food and service. I love the ricotta dumplings, the kale salad, and the burger.
Bistro Margeaux
An upscale French restaurant with 1920s inspired decor within the Waldorf Astoria in the Gold Coast, the menu includes items like duck wings a l’orange, steak frites, and dover sole. It’s a great date night spot or a fitting location for a special occasion brunch.
Southport Grocery
A cafe/market with one of the best brunches in Chicago.
Mia Francesca
A family-owned Italian restaurant serving up classic pastas like spaghetti and meatballs and spinach ravioli.
Le Colonial
An elegant French-Vietnamese restaurant in the Gold Coast serving lunch and dinner.
Farmhouse
A casual gastropub with a big beer list and excellent farm to table food.
Quartino
An affordable small plates Italian restaurant in River North.
The Hampton Social
This restaurant has a pair of Instagram-ready locations that specialize in East Coast seafood and cuisine.
Chicago Food Halls
Having a hard time picking a restaurant? Check out these food halls that provide a wide range of dining options.
Time Out Market
A large food hall in the West Loop featuring 18 restaurants and a rooftop bar. The restaurants are mini versions of some of Chicago’s top restaurants including Lost Larson, Mott St, and The Purple Pig.
Politan Row
A food hall with 13 vendors serving a variety of cuisine including Asian street food, tacos, hummus, Cajun cuisine, and vegetarian food. In the summer it has an outdoor beer garden.
Revival Food Hall
A food hall in the Loop with 15 fast-casual food stalls serving poke, tacos, dosas, fried chicken, sandwiches, burgers, ramen, empanadas, and more. this food hall caters to those working in the loop and is open from 7am-7pm Monday to Friday. It is closed on weekends.
Chicago French Market
It’s called the French Market, but you can find 30+ vendors selling food from all over the globe here.
Aster Hall
A food hall on the upper floors of the 900 North Michigan Shops. One level is more casual, while the other has a more formal restaurant.
Latinicity
A food hall within Block 37 that specializes in Latin American cuisine. I love the Peruvian food here.
Wells Street Market
A food hall in the Loop, just across the river from Merchandise Mart, with 9 fast-casual restaurants and a bar. It’s open 7:30am-7pm Monday to Friday and is closed on weekends.
Chicago’s Best Nightlife
These cocktail lounges and dive bars are sure to give you a memorable night out.
Three Dots and a Dash
A tiki bar in the basement below Bub City – find the entrance in the alleyway behind Bub City.
The Drifter
A speakeasy with live entertainment in the basement of the Green Door Tavern.
Lazy Bird
A cocktail bar and music lounge in the basement of the Hoxton Hotel. The menu features 52 different cocktails.
The Aviary
A sister restaurant to Alinea known for elaborate futuristic cocktails. Reservations are needed.
The Office
Located below The Aviary, this is a speakeasy serving classic cocktails and small plates. Make a reservation in advance.
LondonHouse
A rooftop bar/restaurant that provides some of the best views of the Chicago River and the skyline. It’s a popular spot for happy hour.
Cindy’s Rooftop
A rooftop bar/restaurant with views of Grant Park, Millennium Park, and Lake Michigan. It’s also one of the best places to see the summertime fireworks.
Tao
A large nightclub that recently opened and has become very popular.
Innjoy
This is the bar you go to if you want to dance your heart out. They are known for their 80s/90s dance party on Saturday nights.
Rainbo
A grungy dive bar in Wicker Park with lots of personality that was featured in High Fidelity.
Queen Mary Tavern
A cocktail bar in Wicker Park with a maritime theme and some of the best craft cocktails in the city. We love to combine dinner at Pub Royale with cocktails at Queen Mary on date night.
Untitled Supper Club
A large speakeasy themed bar/restaurant in River North with live entertainment.
The Darling
A two level cocktail lounge in the West Loop that hosts throwback entertainment at 7:30.
Old Town Ale House
A cash-only dive bar across the street from Second City.
Violet Hour
A speakeasy across from Big Star with an entrance marked with only a light. It’s considered one of the best cocktail bars in the country.
Punch Bowl Social
A 30,000 square foot space with a bar, arcade, bowling, and karaoke.
Lost Lake
A tropical cocktail bar in Logan Square that stocks 275 varieties of rum.
Hubbard Street
A street in River North that is densely populated with bars. This is one of the most popular places to go for a night out.
Wells Street
A street in Old Town with many bars, these bars tend to be more casual than the ones on Hubbard Street.
Chicago Breweries
Chicago has more breweries than any other city in America. There are 167! Here are my picks:
Goose Island
The brewery behind 312 has a Brewhouse on Clybourn that has a taproom, restaurant, and brewery tours.
Revolution
Revolution has both a brewing facility with a taproom that offers tours and a brewpub in Chicago. Their beer “A Little Crazy” is one of my go-to beers and Charles loves the Cross of Gold.
Half Acre
Half Acre’s Tuna, a citrusy session India Pale Ale, is one of my favorite beers. The brewery has breweries/taprooms on Lincoln Avenue and on Balmoral Avenue.
Lagunitas
Lagunitas has a production facility and taproom in the Pilsen neighborhood.
Off Color Brewing
This brewery has a taproom called The Mousetrap in Lincoln Park serving beer and cocktails. They don’t have a kitchen but you are welcome BYO food (there is a massive Whole Foods with a a huge to-go section next door). They offer free brewery tours on Sundays – register in advance.
Ballast Point
A taproom with 40 taps serving Ballast Point brews in the Fulton Market District, the brewery was sold in March 2020 and the taproom has closed for a refresh.
Metropolitan Brewing
We love the Flywheel Lager produced by this Chicago brewery. Their brewery/taproom in Avondale is open daily – there is no kitchen but guests can BYO food.
Live Music in Chicago
These bars and restaurants are known for having live music on a nightly basis.
The Green Mill
This is Chicago’s essential jazz bar, and Al Capone hangout. I love the atmosphere and the music is always great. Like with most blues and jazz bars, expect 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.
B.L.U.E.S.
Also in Lincoln Park and very close to Kingston Mines, B.L.U.E.S. is a bar with nightly live blues music.
Andy’s Jazz Club & Restaurant
A River North jazz lounge with live music 7 nights a week.
Bub City
This barbecue joint is known for showcasing country music and hosting a weekly live music karaoke.
Buddy Guy’s Legends
A blues club in the loop with live music every night and New Orleans inspired food.
Concert Venues in Chicago
Many of these venues are managed by Jam Productions, so if you are looking to see a concert, their website is a good place to start.
Thalia Hall
An intimate landmark venue in Pilsen that primarily hosts concerts, but there are some comedians and other shows on the calendar too.
The Vic
A concert venue in Lakeview that hosts indie artists and mid-sized concerts. On the nights without concerts they usually show movies.
The Aragon Ballroom
One of the larger venues in Chicago, The Aragon Ballroom can fit 5,000 people. It’s located in Uptown just off the Lawrence red line stop.
The Riviera
Located across the street from The Aragon, The Riviera is smaller with a capacity of 2,500 people.
Park West
What opened as a vaudeville and movie theater in 1916 is now a 1,000 guest concert venue. The schedule has a mix of bands and comedy acts.
The Chicago Theater
I like this theater because shows here are seated and I’ve always gotten a good view no matter where I have been seated. I’ve seen concerts here as well as book talks and comedy shows. This venue has a diverse line up. Plus, is in the Loop and so easy to get to!
Schubas Tavern
A bar/concert venue in an old brewery in Lakeview.
Lincoln Hall
Located in Lincoln Park, Lincoln Hall is a midsized concert venue with a bar and a restaurants.
Empty Bottle
An indie music venue in the Ukrainian Village.
Metro
An intimate concert venue in Lakeview/Wrigleyville that is popular with indie and alternative bands.
Subterranean
A venue just off the Blue Line in Wicker Park that hosts a wide range of concerts and events.
City Winery
A West Loop winery/restaurant with a concert venue. I like this venue since it is small and fun to visit with friends.
House of Blues
A concert venue that hosts a gospel brunch on Sundays.
Bottom Lounge
A venue in the West Loop that features indie acts and emerging artists.
United Center/Soldier Field/Wrigley Field
The biggest concerts take place at these 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.
Several theaters in downtown Chicago produce musicals and plays. Some are traveling Broadway productions while others originate in Chicago.
Steppenwolf Theatre
A Lincoln Park theatre company that has won 12 Tony Awards. The theatre has three stages and produces up to 16 plays each year.
Lookingglass Theatre
This theater is a place to see new plays and was founded in 1988 by Northwestern University graduates.
Chicago Shakespeare Theatre
This theater on Navy Pier has more than Shakespeare, they also premiere new plays and musicals like The Notebook.
Hubbard Street Dance
A contemporary dance company based in Chicago that performs at the Harris Theater.
Lyric Opera
Chicago’s home for opera has a season that runs from the early fall to the summer each year. They produce about 9 operas each season.
Joffrey Ballet
The Joffery Ballet’s classic ballet performances take place at the Lyric Opera. They produce shows like Romeo & Juliet and The Nutcracker.
Comedy Clubs in Chicago
Comedy is a big deal in Chicago, and seeing a comedy show is one of the things to do in Chicago that can’t be missed. From world famous comedy theaters to smaller neighborhood venues, here are some of the best places to see comedy in Chicago.
Second City
One of the most iconic comedy venues in America, Second City is an improv theater in Old Town where many SNL cast members trained. They have multiple stages and shows.
Zanies
Also located in Old Town, Zanies hosts well-known stand up comics.
iO Theater
A Lincoln Park improv theater with four stages and shows every night of the week.
Laugh Factory
A larger comedy venue that hosts stand up comedians.
The Comedy Bar
A standup comedy venue with two stages. They host stand up comedians, open mics, and ensemble shows.
UP Comedy Club
This comedy club features a mix of improv, stand up, and sketch comedy.
CSz Theater Chicago
A theater in Lakeview that treats comedy as a sport where two improv teams compete for applause.
The Annoyance Theatre
A two stage theater in Lakeview East that showcases improv, sketch comedy, stand up, musicals, and plays.
Where to Shop in Chicago
The Magnificent Mile
The Mag Mile is a mile-long stretch of Michigan Avenue known for upscale shopping. The Mag Mile starts on the north side of the Chicago River and ends in the Gold Coast. Shops on the Magnificent Mile include Neiman Marcus, Saks, Burberry, Tiffany & Co., and Gucci. Many of Chicago’s finest hotels including the Peninsula, the Park Hyatt, and The Drake are on this stretch of Michigan Avenue.
900 North Michigan Shops
A luxury shopping mall with a Bloomingdales and a food hall.
The Shops at North Bridge
An urban shopping mall that is home to Nordstrom among other shops.
Water Tower Place
Another urban mall, this once is known for being home to American Girl Place and Macy’s. In general, the retailers here are a bit more affordable.
Block 37
A shopping center in the Loop with shops like Anthropologie, Zara, Banana Republic, Sephora, The Disney Store, Magnolia Bakery, and more.
The Gold Coast
This neighborhood is the best place for luxury shopping in Chicago. You will find retailers like Hermes, Gucci, and Dior here.
Lincoln Park
Both Armitage Avenue and Halsted Street in Lincoln Park have a mix of independently owned boutiques like Art Effect, Monica + Andy, Aroma Workshop, and All She Wrote plus some larger retailers like Bonobos, Lush, francesca’s, and Allbirds.
Wicker Park
This hipster neighborhood has a mix of vintage clothing shops, locally owned boutiques, bookstores, record shops, and a few national retailers. North Milwaukee Avenue between Damen and Division is where many of the stores are concentrated.
Andersonville
The Andersonville neighborhood in Chicago has a great mix of antiques stores and locally owned boutiques. Some of my favorites are the Andersonville Galleria, Andersonville Antiques, Roost, Scout, and Brimfield.
Fashion Outlets of Chicago
Located near O’Hare in Rosemont, this is a luxury fashion outlet with stores including Bloomingdales, Burberry, Gucci, JCrew, Lululemon, Neiman Marcus, Prada, and Saks Off Fifth.
More Chicago Travel Guides:
What to do in Old Town
What to do in the West Loop
What to do in Wicker Park
What to do in the Gold Coast
What to do in River North
What to do in Downtown Chicago/The Loop
What to do in Lakeview
What to do in Streeterville
What to do in Lincoln Park
200+ Things to do in Chicago
The 20 Best Things to Do in Chicago in Summer
What to Know about Visiting Chicago
Wintertime Date Ideas for Chicagoans
The Ultimate Chicago Travel Guide