Are you a bit bored in Chicago at night? Or not sure what to do in the evening? I had the same problem but after some research, we found some fun activities and attractions worth visiting! Chicago, America’s mid-west metropolis and bona fide world-class city is famous for its food, music, and epic skyline. In this article, we’ll show you even more fun things to do at night.

1. Cruising

Cruising is a great way to relax and see Chicago at night. Like with most activities near the water, bring a light jacket as it can get breezy out on the lake. Here are some recommended evening cruise tours in Chicago.

  • Private Sunset Sails – A bit more pricey, but for a unique and personal experience, set sail on this luxury boat on a 2-hour tour around Lake Michigan.
  • Lake Michigan Sightseeing Cruise – For a cheaper option, board the Star of Chicago. Take in the silhouette of the skyscrapers as the sun sets behind them and the city lights start to ignite. The evening cruise leaves Navy Pier at 7:30pm.

There are a number of other unique cruises, some include dinner, architecture talks, and even fireworks.

  • Prices: from $23 USD
  • Duration: 1-3 hours

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2. Night Walking

There are a number of interesting places in Chicago for casual night walks. Chicago Lake Shore is one popular area to stroll around. It’s over 15 miles of urban green space and is home to museums, the planetarium, the aquarium, and Soldier Field. The lakeshore is also dotted with beaches, so get your feet in the sand!. If you want to see the towering skyscrapers light up the skies, the Riverwalk is the best option. Besides architecture, there are plenty of things here other than just walking. If you’re feeling a bit peckish during your walk, try some of the great restaurants that line the river. For a real insight into Chicago at night, it may be worth checking some of the many tours available. This includes unique experiences like pub walks, haunted talks, and professional photography guides.

  • Prices: from $5 USD
  • Duration: 1-3 hours

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3. Helicopter Tours

There’s hardly a better way to see a city lit up at night than from above in a helicopter. Fly by the skyscrapers, over Lake Michigan, and get look at the city’s landmarks from the air. There are helicopter tour operators in the city that offer night tours that range from 15 minutes to an hour. If you’re game enough, there are even “learn to fly” tours.

  • Prices: from $295 USD
  • Duration: 30 minutes – 1 hour

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4. Willis Tower Skydeck

Get a view of the city from the top of the tallest building in the Western Hemisphere. The world-famous Sears Tower’s (now the Willis Tower) Skydeck offers visitors the chance to survey the entire region during the day. At night, it’s easily one of the best vistas of Chicago’s lights. Subject yourself to a little vertigo on The Ledge, a glass terrace jutting out from the side of the tower. You can look straight down to the sidewalk 1,353 feet below your feet.

  • Prices: from Adults $28 USD, Kids $22 USD
  • Opening Hours: 9am-10pm
  • Address: 233 S Wacker Dr, Chicago, IL 60606, United States

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5. 360 Chicago

Formerly the John Hancock Observatory, 360 Chicago is Skydeck’s rival. But you should take advantage of both since they offer different vantage points. Further uptown and across the river, 360 Chicago, not to be outdone by The Skydeck’s “Ledge”, boasts 360’s “Tilt”. As you stand in front of a bank of windows, grab bars on either side. Then the floor and windows “tilt” forward till you’re facing about 35° down toward the sidewalk. After the Tilt, grab a drink at Bar 94 or The Signature Lounge on the 96th floor to enjoy the night views.

  • Prices: Adults $30 USD, Kids $20 USD
  • Opening Hours: Sunday to Thursday 9am-9pm; Friday & Saturday 9am-11pm
  • Address: 875 N Michigan Ave 94th floor, Chicago, IL 60611, United States

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6. Dining Experiences

Chicago is famous for their pizzas, steaks, and sandwiches. But at night, there are more unique experiences. You can catch a cruise, enjoy buffets, and watch fireworks. Watch traditional live shows while eating Spanish Tapas. Or find out why Chicago is so famous for pizzas on a sampling tour. For a real party vibe, you can always rely on Hard Rock Cafe and its juicy burgers.

  • Duration: 2-3 hours

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7. Chicago Entertainment

If you want more than just food, some dining experiences include entertainment like interactive detective plays or a Medieval times show. You could even see major productions like Aladdin or the long running Blue Man group. Alternatively, check out venues such as Auditorium theatre and Chicago Symphony Center for various shows. Prefer an old fashioned movie? Grab a blanket, chair, and some snacks, then head down to Millennium Park for a movie. Every summer, Chicago sets up screens in parks all over the city and shows films ranging from Hollywood’s Golden Age to recent hits. Check the schedule and see if any of your favorites are showing.

  • Duration: 2-3 hours

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8. Alder Planetarium

Jutting out into Lake Michigan on the NE point of Northerly Island, Alder Planetarium is a museum dedicated to the science of astronomy.  This place has enough cool stuff to see and do to keep everyone engaged. But it’s the Doane Observatory telescope that surpasses it all.  Come to the Doane at Dusk nighttime telescope viewings with accompanying lectures by staff astronomers. The telescope is powerful enough to furnish clear views of our nearby celestial neighbors. You might even see galaxies that are trillions of miles into deep space.  Check the schedule on their website, and keep in mind the telescope viewings are weather permitting.

  • Prices: from Adults $19 USD, Kids $8 USD
  • Address: 1300 S Lake Shore Dr, Chicago, IL 60605, United States

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9. Navy Pier

If you have a family with young kids, this will be the best place to go. Navy Pier has rides and games to keep everyone entertained all night. Check out the views from the popular Centennial Wheel, or jump on the classic carousel. Different restaurants are open late so you can grab a bit at any time. Some cruises also depart from here, so it’s the best hub for most Chicago night activities.

  • Prices: No admission prices. Cost of rides vary, starting from $2 USD.
  • Opening Hours: Sunday to Thursday 10am -10pm; Friday & Satruday 10am-12am
  • Address: 600 E Grand Ave, Chicago, IL 60611, United States

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Chicago is a buzzing city with an endless parade of amazing things to do after the sunset. No matter what time of year you find yourself in Chicago, there should be something on this list to keep you busy at night. For more activities, read these guides:

If you need a place to stay, check out these hotels:

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For all new cities, I go overboard on my itinerary, just to see every major attraction. Countries I've visited include New Zealand, Singapore, Hong Kong, China, Cambodia, Japan and Thailand. Mostly Asian countries. Next target - Europe!