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Chicago Mural in the City
After Five Guides,  North America

Chicago After Five: Explore the Windy City at Night

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Located along Lake Michigan, Chicago is third most populated city in the United States. Chicago was not only home to the first skyscrapers, but is also home to a wide variety of companies. If you find yourself in the Windy City for work or a conference, there are many activities that will allow you to see Chicago at night.

Climb to the top of the Willis Tower

Formerly known as the Sears Tower, the Willis Tower the second tallest building in the United States. For $22, you can take an elevator to the Skydeck to get a panoramic view of the city. I went on a Wednesday afternoon right after work, and there were no lines at all. If you are in Chicago at night, this is the perfect time to visit the tower and take a few pictures on The Ledge, glass ledges you can walk out onto. The Skydeck is open 365 days a year: March through September from 9:00 am to 10:00 pm, and October through February from 10:00 am to 8:00 pm.

See the Bean and enjoy the city’s reflections

The proper name of the famous Chicago sculpture is the Cloud Gate, but everyone just calls it the Bean. Since Millennium Park in a public park, you can visit the Bean at any time of day – and if you go in the evening after work, there will be less people around and you can take better pictures! You will be able to take a great photograph Chicago at night’s city skyline reflected in the sculpture. You can also walk around the rest of Millennium Park and see other sculptures available.

Chicago The Bean Cloud Gate at Night

Stroll along the Chicago Riverwalk

The Chicago Riverwalk is a 1.25 mile path along the north side of the river. This area is busy after work, with commuters walking home and happy hours taking place during the spring. It is free to walk along and enjoy the path, and you can watch the tour boats stroll by as the sun sets. Check back on the website during the spring to see kayak and tour boat options.

Visit the Navy Pier and watch the fireworks

During the week, the Navy Pier closes at 8:00 pm. With different attractions, shopping, and restaurants, the Navy Pier could be a nice afternoon spent with the team. If you are in Chicago at night, dinner cruises are available and offer gorgeous tours with a meal. Some sightseeing and dinner cruises board as late as 6:30 pm and finish around 9:00 pm. Every Wednesday, Chicago also shoots fireworks in the harbor.

Chicago at Night Dinner Cruise Views

Dine at Harry Caray’s 7th Inning Stretch and visit the Chicago Sports Museum

Sports fans would have a blast spending Chicago at night at the Water Tower Place on Chicago’s Magnificent Mile. Harry Caray’s 7th Inning Stretch offers typical American comfort food including burgers, pizza, and tacos. The Chicago Sports Museum, free with dinner or $6 on its own, is open until 8:30 pm during the week, and can be toured as soon as you are finished eating.

Stuff your mouth with deep dish pizza

Did you really visit Chicago at night if you didn’t try the famous deep dish pizza? Two of the most popular chains include Giordano’s or Lou Malnati‘s. Keep in mind that the lines for these restaurants are usually pretty long, possibly with waits over one hour. Deep dish pizza also may take over 30 minutes to cook. While most of the restaurants do not allow reservations, you have the option of ordering your pizza while you wait, or even ordering ahead and taking your pizza to-go. The last time my coworkers and I were in Chicago, we ordered before we left the office, picked it up, and ate it in our hotel lobby. Anything for deep dish!

There is so much to see in Chicago at night, and this guide only covers some highlights downtown.


Check out the rest of the Midwest:


Michelle Maraj is the founder of Travel After Five, and is an analytics consultant who frequently gets the opportunity to travel for work.

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