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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 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

A trip to this midwestern city can be budget-friendly too. Find affordable or free things to do in Chicago to fill your days, saving your money for dinner or drinks.

Cheap or free things to do in Chicago include:

  • Visit Lincoln Park Zoo, one of the oldest free zoos in the country
  • Stop and smell the flowers at Lincoln Park Conservatory & Gardens
  • Watch a water and light show at Clarence Buckingham Memorial Fountain
  • Sign up for Chicago Greeter, a free program that pairs a local volunteer with a visitor to show you around town
  • Visit The Art Institute of Chicago offers a free museum day

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

A two-day respite can help recharge your senses before Monday. Find excitement before you return to the office — start your weekend off right by finding new things to do on a Chicago weekend.

Things to do in Chicago this weekend include:

  • Walk through more than 15,000 works in The Smart Museum of Art
  • Go see some of Chicago’s finest comedy at Annoyance Theatre & Bar
  • Get out on the water with Mercury cruises
  • Find your new favorite beer at Hopleaf
  • Recharge your sense of wonder at the Museum of Science and Industry

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

Whether you want to share pizza or listen to the blues, the Windy City has a lot to offer couples looking for a fun date. Go out with your special someone, one night at a time with plenty of romantic things to do in Chicago.

Date night ideas near Chicago include:

  • View the works of local photographers at The Museum of Contemporary Photography
  • Buy tickets to a show at League of Chicago Theatres
  • Listen to the blues at Buddy Guy’s Legends
  • Share a bottle of wine at Chi Bar
  • Try locally-made whiskey at KOVAL Distillery

Traveling to the Windy City has enough options to warrant many group trips to come. Stay organized when you travel by picking out your group activities in Chicago ahead of time.

Things to do with your friends near Chicago include:

  • Earn a strike at 10pin Bowling Lounge in downtown Chicago
  • Listen to live music at Bub City
  • Meet up for a couple beers at Local Option
  • Puzzling your way out of The Escape Room Chicago
  • Jet ski on Lake Michigan with Chicago Water Sport Rentals

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

While it’s easy to visit The Bean and call it a day, Chicago has much more to offer. For foodies, get a taste of the food items that have earned their namesake from the Windy City.

Must-see places near Chicago include:

  • Walk around Wicker Park, or any other of Chicago’s 77 walkable neighborhoods
  • Eat an Italian sandwich at Johnnie’s Beef
  • Get deep dish Chicago pizza at Pequod’s in Lincoln Park or at Burt’s Place for a road trip
  • Order a Chicago-style hot dog with the retro dive Superdawg
  • Explore vintage video games at Video Game Art Gallery