5 Fun Ways to Spend the Evening in Chicago

Whether you’re visiting Chicago for a long period of time or just seeing friends for the weekend, you never need to have a boring evening in the Windy City. With iconic food, interesting museums, unique live shows, exciting sports venues, and a vibrant nightlife, it can be difficult to decide how you’ll spend your evenings—especially since Chicago truly offers a bit of everything. We’ve picked out five evening activities that you should consider on your next visit.

Go to a comedy show

Chicago is home to some of the world’s premier comedy clubs. The world famous Laugh Factory is open seven nights a week. Guests may recognize the iconic background from viral YouTube clips with many of the world’s top comedians. They host 5-7 comedians each night and offer a variety of drink deals, along with being open for private parties.

The Second City is another destination for a night full of laughter. It is one of Chicago’s oldest comedy clubs and has been open since 1959. Past comedians at the historic club include Tina Fey, Bill Murray, and Steve Carrell. Not only does The Second City offer live shows, but you can also pay to take classes. Other comedy options include Zanies Comedy Club and The Comedy Bar, which are both open every night of the week. Zanies is an adult only club with a two-drink minimum, while the Comedy Bar is open to all ages and has free open mic nights.

Catch a musical or live performance

Some of the best plays and musicals are available to watch in Chicago on any given evening. Head to Mercury Theater to enjoy Priscilla: Queen of the Desert, which plays until mid-September. The musical features a combination of disco and dance music. Fans of songs such as “It’s Raining Men” and “I Love The Night Life” will greatly appreciate the entertainment.

Blue Man Group is another option for live entertainment. The show is based on non-verbal communication and has a powerful combination of art and music. Running between 90 to 105 minutes, Blue Man Group prides itself on having every show be unique. For more information on shows in Chicago, check the schedule of The Chicago Theatre or Cadillac Palace Theatre for an abundance of options.

Go on a nighttime food tour

For a combination of exercise and culinary enjoyment, take the Bikes, Bites & Brews Tour. The tour covers all of the bases you’ll want as a visitor. The tour gives samples of pizza, hot dogs, brownies, and beer as you travel through some of Chicago’s most popular neighborhoods.

On this food tour, people will get to see different Chicago neighborhoods including Streeterville, Gold Coast, Wrigleyville, and stop at Buckingham Fountain in the center of Grant Park. In just a few hours, you can learn about the city and try some of the most iconic foods available in Chicago.

Enjoy the nightlife

If you’re feeling up for it, spend your evening exploring Chicago’s bars, restaurants, and dance clubs. Whether you want to explore food options with friends or spend a night dancing, there’s countless options available to you in the Windy City. TAO is a high-end hybrid of a restaurant and club in Chicago that is well-known across the world, featuring other locations in New York and Los Angeles. If you want Mexican cuisine and a vibrant spot to bring friends, go to Federales in the West Loop. Michigan Avenue and River North are also great areas to walk around and explore the options available to you, from delicious Italian food at Quartino Ristorante to classic cocktails at The Gameroom.

Your evening wouldn’t be complete without visiting the Albert, located inside of Hotel EMC2 in Streeterville. The dinner and bar menu feature flavorful Italian inspired dishes, fine wines, and mouth watering desserts. From the creative recipes to the surrounding books and art, spending a few hours at the Albert is unforgettable.

Watch a movie at an outdoor theater

There are a number of drive-in theaters in Chicago that serve as a fun alternative to a traditional movie-going experience. Pack a bag of snacks and drinks and spend your evening enjoying a movie under the night sky.

Located in Pilsen, ChiTown Movies is a spacious drive-in theater. Popcorn, tacos, wings and beverages can be ordered and delivered to your car. For a great view of the city’s skyline, go to Rooftop Cinema Club in Fulton Market. Tickets to Ferris Bueller’s Day Off, Romeo and Juliet, and other classics are available through early September. Other prominent outdoor theaters in Chicago include Patio Theater, and if you’re seeking a live performance, Theater on the Lake.

Planning your trip

With so many fun evening activities, you won’t regret booking a trip to Chicago. From the live theater and shows to the vibrant nightlife, your nights in the Windy City will never lack in entertainment. If you’re seeking a trip to Chicago this summer, consider booking a room at a boutique hotel like Hotel EMC2, located in the heart of the city.

Need a place to stay while visiting Chicago? Book your reservation here.