7 Fun Things to Do in Chicago

Are you traveling to Chicago? We have to admit, the Windy City is one of our favorite big city destinations. Chicago is a world-class city with enough to keep you busy for years. For starters, here are seven things to do in Chicago that you won’t want to miss:

Visit the Art Institute

Chicago is practically the Paris of the US. There are so many museums you could spend months seeing the exhibits and collections. At the top of your list should be the Art Institute of Chicago, an art museum that rivals the world’s best.

In addition to permanent collections that span all historical periods, the Art Institute always has fantastic temporary exhibits from around the world. You can purchase tickets online to make your visit easier. Don’t forget to snap a picture with the famous lion sculptures flanking the front entrance on Michigan Avenue!

Head to the Museum of Science and Industry

If the Art Institute sounds a bit too sedate, head on down to the Museum of Science and Industry in Hyde Park. With cool exhibits for children and for the young at heart, it’s the perfect place to spend a rainy day. Many of the exhibits are hands-on. Traveling to Chicago for work? The Museum of Science and Industry hosts events too–a cool way to kick off a conference or meeting.

Nestled among everything there is to do in Chicago is the James Hotel.

Walk the Magnificant Mile

Walking the 13-block segment of North Michigan Avenue between the Chicago River and Oak Street will give you a taste for the style, cuisine, and architecture of the city. The “Mag Mile” is one of the world’s top-10 dining and retail destinations. You’ll see some of the most seductive shops, best restaurants, and incredible buildings, so make plenty of time for stops and photo ops.


Eat Like a Native

All that walking is bound to make you hungry, so chow down like the locals do when your appetite kicks in. First, be sure to grab a hot dog somewhere in your travels, either from the many street vendors or from the storefront locations that specialize in Chicago-style hot dogs. A Chicago hot dog isn’t just any hot dog but a “char dog,” grilled to perfection and topped with chopped onions, peppers, and condiments.

Quench your thirst at the Berghoff Bar, a Chicago institution since the 19th Century. The Berghoff was the first place to get a liquor license in Chicago when Prohibition was lifted. It served men only until 1969.

See the City from Above at the 360 Observation Deck

If you don’t have a fear of heights, be sure to check out the city view from up high at the 360 Observation Deck, formerly the John Hancock Observatory. You’ll love the incredible views of the skyline and Lake Michigan. Really want a thrill? Get a ticket for Tilt, which gives you a bottomless vista from 1,030 feet up.

Walk or Bike the Lakefront Trail

You can’t go to Chicago without walking or biking the Lakefront Trail. In snowy weather, you’ll even find cross-country skiers there! In fact, many people think winter is the best time to visit Chicago. It’s the perfect place to get some exercise and take in the incredible skyscrapers nearby. Connecting four lakefront parks, beaches, and marinas, there’s something for everyone on the Lakefront Trail.

Explore Navy Pier

You may have spied Navy Pier from the air if you flew into Chicago. A renovated historic location with cultural attractions, eateries, shopping, and even ice skating, Navy Pier is ideal for families, dates, or just exploring on your own. Don’t miss the Centennial Wheel, an enormous Ferris wheel that affords one-of-a-kind views of the city.

Our list of the best things to do in Chicago is only the beginning. Choose a hotel from Triphop’s great selection and get travel rewards of up to 15% Cash Back for members. With more than 550,000 hotels worldwide, you can earn top Cash Back and hotel deals wherever your next trip takes you.