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Top Things To Do In Chicago

Chicago is a city where arts, culture, and commerce whirl together for a fun, skyline-backed Midwest destination. Before you storm the city, start planning out all of the things to do in Chicago while on vacation. Get whisked away by all that the Windy City has to offer with some of the below vacation ideas.

Chicago Explorer Pass: Entry to 3, or 5 Things to Do from 25+ Museums, Navy Pier, Cruise, Observation Decks & More
Go City - Chicago Explorer Pass
22 Locations
$49.00
Chicago Explorer Pass: Entry to 3, or 5 Things to Do from 25+ Museums, Navy Pier, Cruise, Observation Decks & More
10+ bought
Admission Ticket to KidsWork Children's Museum for One, Two, Four, or Six (Up to 33% Off)
KidsWork Children's Museum
Frankfort
4.6
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$8.00 $6.00
25% discount_off
Admission Ticket to KidsWork Children's Museum for One, Two, Four, or Six (Up to 33% Off)
60-Minute Scenic  Flight for Two Passengers from Chicago Aerial Tour (Up to 26%  Off)
Chicago Aerial Tour
Wheeling
4.7
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$299.00 $219.00
26% discount_off
60-Minute Scenic  Flight for Two Passengers from Chicago Aerial Tour (Up to 26% Off)
Visit for One, Two, or Four to the Chicago History Museum (50% Off)
Chicago History Museum
Chicago
4.7
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$19.00 $9.50
50% discount_off
Visit for One, Two, or Four to the Chicago History Museum (50% Off)
1-Year Patron or Family Membership at Polish Museum of America (Up to 46% Off)
Polish Museum of America
Chicago
5.0
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$50.00 $29.00
42% discount_off
1-Year Patron or Family Membership at Polish Museum of America (Up to 46% Off)
Admission at International Museum of Surgical Science  (Up to 50% Off); Four Options Available
International Museum of Surgical Science
Chicago
4.6
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$34.00 $18.00
47% discount_off
Admission at International Museum of Surgical Science (Up to 50% Off); Four Options Available
Admission to Aurora Regional Fire Museum for One, Two, or Four at Aurora Regional Fire Museum (Up to 40% Off)
Aurora Regional Fire Museum
Aurora
4.7
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$5.00 $3.50
30% discount_off
Admission to Aurora Regional Fire Museum for One, Two, or Four at Aurora Regional Fire Museum (Up to 40% Off)
90-Minute Chicago Architecture Boat Tour One, Two, Three, or Four (Up to 40% Off)
Tours and Boats
Chicago
4.6
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$49.00 $29.00
40% discount_off
90-Minute Chicago Architecture Boat Tour One, Two, Three, or Four (Up to 40% Off)
General Admission Tickets to Volo Auto Museum (Up to 26% Off)
Volo Auto Museum
Volo
4.7
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$15.00 $11.00
26% discount_off
General Admission Tickets to Volo Auto Museum (Up to 26% Off)

Chicago has a lot to be proud of. Whether it’s iconic art installations or eateries along a popular pier, the people of Chicago know how to keep busy. Start off your vacation by knocking some of these iconic Chicago activities off your todo list.

The best things to do in Chicago include:

  • Check out the mind-bending reflections at Cloud Gate, also known as The Bean
  • Head to Millennium Park to take a selfie with the Crown Fountain
  • Climb Willis Tower and get a view of the Chicago skyline
  • Explore the 50 acres of gardens, amusement rides, shops, and eateries at Navy Pier
  • Go shopping at The Magnificent Mile, Chicago’s premier shopping destination

Events in ChicagoView All

$12 for Admission for One to a Comedy Show at Improv Playhouse (Up to $20 Value)
Improv Playhouse
2 Locations
4.5
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$20.00 $12.00
40% discount_off
$12 for Admission for One to a Comedy Show at Improv Playhouse (Up to $20 Value)
$15 for Two-Day General Admission for Two People to Randolph Street Market ($20 Value)
Randolph Street Market
Chicago
4.4
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$20.00 $15.00
25% discount_off
$15 for Two-Day General Admission for Two People to Randolph Street Market ($20 Value)
Standup for Two at Riddles Comedy Club – Friday Only (January 31–September 25)
Riddles Comedy Club
Alsip
$30.00 $17.00
43% discount_off
Standup for Two at Riddles Comedy Club – Friday Only (January 31–September 25)
70+ bought
MyOhMy: A Drag Show Extravaganza! on Friday, May 29 or Friday, June 5
MyOhMy: A Drag Show Extravaganza!
online_deal
$9.95 $4.00
59% discount_off
MyOhMy: A Drag Show Extravaganza! on Friday, May 29 or Friday, June 5
50+ bought
Colin Mochrie and Brad Sherwood: Scared Scriptless on Wednesday, May 27 at 8 p.m.
Colin Mochrie and Brad Sherwood: Scared Scriptless
Rockford
$60.56 $36.33
40% discount_off
Colin Mochrie and Brad Sherwood: Scared Scriptless on Wednesday, May 27 at 8 p.m.
30+ bought
Sugar Brown’s Bedroom Burlesque Virtual Show on Saturday, May 30
Sugar Brown’s Bedroom Burlesque Virtual Show: Stimulus Package
online_deal
$22.85 $10.00
56% discount_off
Sugar Brown’s Bedroom Burlesque Virtual Show on Saturday, May 30
8 bought
Mudd Fest 2020: Puddle of Mudd, Fuel, and Trapt on Saturday, September 5
Mudd Fest 2020: Puddle of Mudd, Fuel, and Trapt
Addison
$54.52 $35.00
35% discount_off
Mudd Fest 2020: Puddle of Mudd, Fuel, and Trapt on Saturday, September 5
3 bought
Iconic 26 Selfie Hunt for One, Two, or Four at Mile 4 Mile Global (Up to 50% Off)
Mile 4 Mile Global
Chicago
$52.00 $26.00
50% discount_off
Iconic 26 Selfie Hunt for One, Two, or Four at Mile 4 Mile Global (Up to 50% Off)
1 bought
Chippendales@Home! Virtual Party
Chippendales@Home
online_deal
$200.00 $150.00
25% discount_off
Chippendales@Home! Virtual Party
1 bought

Hotels & Accommodations in ChicagoView All

Stay at 2.5-Star Downtown Chicago Hotel
2.5-Star Downtown Chicago Hotel
Chicago
3.8
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$69.30 $59.40
14% discount_off
Stay at 2.5-Star Downtown Chicago Hotel
Stay at Top Secret Hyde Park Hotel in Chicago, IL
4-Star Top Secret Hyde Park Hotel
Chicago
5.0
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$273.88 $127.20
53% discount_off
Stay at Top Secret Hyde Park Hotel in Chicago, IL
Stay at Top Secret Near Hyde Park, Chicago Hotel
3-Star Top-Secret Chicago South Hotel
Chicago
1.0
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$143.20 $136.94
4% discount_off
Stay at Top Secret Near Hyde Park, Chicago Hotel
Stay at The Congress Plaza Hotel & Convention Center in Chicago, IL
The Congress Plaza Hotel & Convention Center
Chicago
3.9
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$143.10 $74.80
47% discount_off
Stay at The Congress Plaza Hotel & Convention Center in Chicago, IL
Stay at Inn of Chicago, IL
Inn of Chicago
Chicago
3.5
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$96.39 $81.09
15% discount_off
Stay at Inn of Chicago, IL
Stay at Top Secret 4-Star Hotel in Downtown Chicago
4-Star Top-Secret Chicago Hotel
Chicago
4.5
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$189.00 $151.20
20% discount_off
Stay at Top Secret 4-Star Hotel in Downtown Chicago
Stay at The Godfrey Hotel Chicago, IL
The Godfrey Hotel Chicago
Chicago
4.5
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$155.73 $76.00
51% discount_off
Stay at The Godfrey Hotel Chicago, IL
Stay at Chicago Magnificent Mile Hotel
2.5-Star Chicago Magnificent Mile Hotel
Chicago
4.2
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$113.98
Stay at Chicago Magnificent Mile Hotel
Stay at Hotel Felix Chicago, IL.
Hotel Felix Chicago
Chicago
4.1
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$127.10 $84.55
33% discount_off
Stay at Hotel Felix Chicago, IL.

Chicago’s 77 neighborhoods feature much for tourists to explore. Whether it’s a scenic view of the skyline or a seeing the city like a local, there’s plenty of tourist attractions in Chicago to knock off your bucket list.

Popular attractions near Chicago include:

  • The Chicago Riverwalk is a hotspot with an iconic view of the city
  • Marvel the architectural feats of Jay Pritzker Pavilion
  • Visit Grant Park, Chicago’s most popular green space
  • Chicago Walking Tours have many stops against Chicago landmarks with a pay-what-you-want model
  • Gawk at the Mies Van der Rohe skyscrapers

If you want to get to know Chicago, you need to do something new every day. After the tourist attractions, start exploring other fun things to do in Chicago.

Fun things to do in Chicago include:

  • Visit McCormick Tribune Plaza, which turns into a picturesque ice-skating rink in the winter
  • Visit Chicago Design Museum, offering changing exhibits related to anything from graphic design and architecture
  • Visit the Field Museum of Natural History
  • Walk on glass at Skydeck Chicago
  • Solve clues and complete challenges in an Urban Adventure Quest

“You can sleep when you’re dead,” is a common expression in this exciting city. From dance clubs to cocktail lounges, Chicago is no stranger to nightlife options.

Things to do in Chicago at night include:

  • Grab a pint at The Map Room
  • Order a cocktail with locally-made vodka from CH Distillery
  • Be charmed by the nonstop party at El Hefe Chicago
  • See the Chicago skyline architecture light up when the sun goes down
  • Enjoy a drink or two at tiki-inspired Three Dots and a Dash

Chicago is teeming with kid-friendly activities. Try going to a water park, botanical garden, planetarium, or even a zoo.

Things to do in Chicago with kids include:

  • Heading to Shedd Aquarium to learn more about marine life
  • Playing with the the interactive exhibits at Chicago Children’s Museum
  • Exploring Peggy Notebaert Nature Museum’s toddler-friendly butterfly spaces
  • Visiting Brookfield Zoo, 216-acre nature park with more than 2000 animal residents
  • Taking the kids to Adler Planetarium

Chicago has museums, cultural hotspots, and art galleries galore. Learning more about the Windy City is one of the best ways to take a break from all that wind.

Chicago things to do indoors include:

  • Explore the expansive Chicago Cultural Center, also known as the “People’s Palace”
  • Visit the National Museum of Mexican Art, which is free to the public every day of the week
  • The Oriental Institute is a part of University of Chicago’s renowned research center for Near Eastern Studies
  • Visit Hyde Park Art Center, a combination of shared art space and community resource
  • Explore the archives of the American Writers Museum

Relax in any of Chicago’s many parks or give water sports a try at the lake or river. Whatever you choose, bring your camera — there’s plenty of things to see in Chicago, don’t miss out on some breathtaking pictures.

Active things to see in Chicago include:

  • Wander the breathtaking native plants at Lurie Garden
  • Climb the wall at Maggie Daley Park
  • Go skating at the Skate Park in Grant Park
  • Try out Bobby’s Bike Hike, a local tour company
  • Visit the Garfield Park Conservatory for a display of houses and outdoor gardens