Did you know Chicago was once a small trading post situated at the mouth of the Chicago River? Probably not. Today, Chicago is the third-largest city in the United States and covers 237 square miles. Those square miles are divided into 77 neighborhoods, each with their own unique traits. While we’re proud of this diversity and size, we realize it can be overwhelming, especially when you’re trying to find something to do after work or on the weekend. Whether you’re a lifelong Chicago resident or you’re just visiting Chi-Town for a few days, you want to spend your time having fun, not sifting through hundreds of bars, restaurants and entertainment options.

Sure, Chicago has plenty of amazing restaurants and bars, or you could catch a movie at one of our great theaters. However, we just don’t think those things would do justice to our amazing city. There’s so much more that goes on in Chicago after dark. And, since you’re reading an article about things to do in Chicago at night, we’re guessing you’ve realized that.

In fact, we might be a little bit biased, but as longtime residents ourselves, we think the best time to experience all Chicago has to offer is after the sun goes down. So, before you head out to just another restaurant or bar — although there are plenty of fantastic ones to be found in Chicago — we hope you’ll consider these top 10 things to do in Chicago after dark.

1. Electric Bikes @ Night Tour

You wouldn’t normally think to jump on a bike after dark, but it is the perfect time to take in the lakefront and skyline view. Starting nightly at 7:30 p.m. and departing from our headquarters in Streeterville, your Bobby’s Bike Hike Chicago tour guide will lead you through a two-and-a-half-hour, eight-mile loop that showcases several of the sights and sounds of downtown Chicago. During the ride, you’ll enjoy the illuminated skyline and take in sights like Olive Park, Oak Street Beach, Millennium Park, Buckingham Fountain, Museum Campus and Soldier Field.

chicago tour at night


If you’re lucky enough to join the tour on Wednesday or Saturday nights in the summertime, you’ll also be able to take in the fireworks at Navy Pier. This beloved downtown tradition synchronizes fireworks to music over Lake Michigan. And, from the seat of a bike, it’s even more spectacular.

2. The Skydeck

Ever wanted to savor a traditional Chicago deep-dish pizza from 103 stories in the air? Now you can dine after hours at this beloved Chicago landmark. Annually, the Skydeck, located inside the Willis Tower — formerly the Sears Tower — hosts 1.7 million tourists. During the day, they take in spectacular views — in fact, on a clear day, you can see 50 miles in all directions. But, after Skydeck Chicago closes to the public, it becomes a once-in-a-lifetime dining experience. You wouldn’t normally think to make a reservation for a pizza dinner, but with only nine tables available each night, you’ll definitely want to call ahead. Catered by Giordano’s Pizza, this three-course dining experience is widely popular with couples looking for a romantic evening and families who want to experience the gorgeous nighttime views of Chicago’s skyline.

3. Adler After Dark

Cocktails, appetizers and … stargazing? Grab an incredible view of the Chicago skyline and the stars beyond at this monthly event. Held every third Thursday, Adler After Dark offers adults 21 and over unlimited access to the Adler Planetarium, along with unique entertainment like guest lecturers and live performers. Included with the price of admission are unlimited sky shows in three state-of-the-art theaters and access to the Doane Observatory. The planetarium’s Café Galileo stays open for this event, serving snacks and entrees. And, guests can purchase beverages from their event bars and sip a cocktail as they take in gorgeous nighttime views. But make no mistake — this isn’t something you’ll want to do just once. With rotating themes every month, you’ll keep coming back again and again and again.

4. The Chicago Theatre

Opened in 1921 as the first “lavish” movie palace in America, today The Chicago Theatre has become one of downtown Chicago’s most beloved live entertainment venues. Residents and frequent visitors will recognize the theatre’s iconic six-story vertical C-H-I-C-A-G-O sign at the corner of State Street and Chicago. When the movie house concept began to decline in the mid-1980s, the theatre was designated for demolition. However, Chicago Theatre Restoration Associates teamed up with the City of Chicago to renovate the building, all while maintaining its original opulence.

When the theatre reopened in 1986, a performance from none other than Frank Sinatra kicked off its second life as a live performance venue. Since then, the theatre has played host to the likes of Kelly Clarkson, Harry Connick Jr., Aretha Franklin, Alicia Keys, David Letterman, Lyle Lovett, Dolly Parton, Prince, Diana Ross, Van Morrison and more. But make no mistake. The Chicago Theatre hosts more than just outstanding musical talent. Their wide variety of offerings include lecturers, comedians and a selection of child-friendly performances if you’re looking for things to do in Chicago at night under 21 years old.

5. Chicago Symphony Orchestra

chicago symphony


Performing more than 100 shows a year at the Symphony Center in downtown Chicago and the Ravinia Festival on Chicago’s North Shore, the Chicago Symphony Orchestra has a global reputation as one of the premier orchestras in the world. The orchestra frequently collaborates with renowned conductors and guest performers from around the globe, making each performance a truly unique experience. Their first performance took place in October 1891, and the music has continued ever since. Today, the Chicago Symphony Orchestra has expanded to offer a wide variety of community-focused musical events, including family-friendly options and their popular “CSO at the Movies” events. Whether you’re in town for a day or you’re here for a lifetime, the opportunities to experience their beautiful music are plentiful.

6. Chicago Helicopter Experience

If you’re really looking to splurge during your night downtown, a helicopter tour just might be the way to do it. The Chicago Helicopter Experience offers twilight tours with unprecedented views of the city. They can accommodate group tours or, if you’re looking for a little romance, you can charter a flight as part of a private evening for two. They even offer fireworks tours on a limited basis. They encourage you to book your tour early to guarantee a seat on the evening you want it, but, because they have to have to meet a certain weight requirement to get up in the air, they do occasionally offer $99 individual seats to help round out a group.

7. Sports

If professional sports are your thing, Chicago is definitely your city. Since the Windy City is home to a variety of sports teams, pro sports is one of the top things to do in Chicago at night during most months out of the year.

chicago sports teams


  • Chicago Bulls: Take in a basketball game at the United Center, located on the Near West Side. Known as the home team of basketball legend Michael Jordan, the Chicago Bulls offer regular home games during their October-through-April regular season.
  • Chicago Blackhawks: One of the “Original Six” NHL teams, the Blackhawks share the United Center with the Bulls, swapping the basketball court for ice during their October-through-April season. Don’t miss these six-time Stanley Cup winners.
  • Chicago Wolves: A member of the American Hockey League, this ice hockey team has become a smash hit in Chicago. With a season running October through April, the Wolves can claim more than 1,000 regular-season wins on their record. Check them out at the Allstate Arena located in Rosemont.
  • Chicago Bears: If you’re ready for some football, head to Soldier Field to see the Bears square off with rival NFL teams. Their season runs from August through December, but don’t let the chilly temps stop you from joining the locals for tailgating before kickoff!
  • Chicago Cubs & Chicago White Sox: Head out to the ballgame with one of our two MLB baseball teams. If you’re a Cubs fan, you won’t want to miss an evening in the “friendly confines” of historic Wrigley Field. While it’s the second-oldest MLB field in the United States, don’t let that fool you. Recent updates to the stadium have added state-of-the-art video screens and the much-loved “Budweiser Bleachers.” The White Sox play at Guaranteed Rate Field during the April-through-September season, and you’ll definitely want to join White Sox fans for some pregame tailgating before the game. And, make sure you don’t miss the fireworks that happen after every home run.
  • Chicago Fire: Named in honor of the Great Chicago Fire in the 1800s, Chicago’s MLS soccer team plays 12 miles south of downtown at Toyota Park. But before you decide that’s too far out of the way, think again. During their regular March-through-October season, fans can jump on the “Pub to Pitch” round-trip bus service that picks up fans from several downtown bars and takes them to the stadium for the soccer match.

8. Blue Man Group

Performing in The Briar Street Theatre, conveniently located near Wrigley Field and the Lakefront, the Blue Man Group has been entertaining Chicago audiences for a long time, and they’re a must-see when you’re downtown. Known for their exciting material showcasing a captivating combination of art, music, comedy and technology, this unique group of performers has captivated more than 35 million people around the world. Blue Man Productions has performers in residence in several cities around the country, but the best thing about their shows is that the group is always updating and refreshing their act with new and exciting material. So, whether you’ve seen them before or you’re looking for something new, you’ll definitely want to catch one of their evening performances.

9. 360 Chicago

Daily until 11 p.m., head to 360 Chicago for breathtaking views of the Chicago skyline and Lake Michigan. Towering 1,000 feet above the Magnificent Mile, 360 Chicago is also home to TILT — an enclosed moving platform that extends over Michigan Avenue from the 94th floor of the John Hancock building. While you’re there, you’ll find plenty of interactive displays with a wealth of information about the city. And, the tower even houses a bar and cafe where you can sit and enjoy food and beverages. That way, you don’t have to rush taking in all the beautiful views.

10. Art Institute of Chicago

You wouldn’t normally think about heading to a museum for a night out, but that’s exactly what you can do at the Art Institute of Chicago. On Thursdays, they’re open until 8 p.m., making them one of the most popular places to go in Chicago at night. Their wide variety of exhibits is always changing, so this is one night out you’ll want to repeat again and again. Illinois residents receive free admission between 5 and 8 p.m., and the museum offers a variety of dining options as well.

Now, Head out and Have Some Fun

Chicago is full of energy, and that energy seems to surge when the sun goes down. Whether you’re looking to enjoy the sights of the city’s skyline, take in a basketball game or have a few laughs at a show, there’s something in this town for everyone, including plenty of 24-hour things to do in Chicago.

chicago events
This list of options only begins to scratch the surface of all the Windy City has to offer. And that’s what makes it so outstanding. In addition to these one-of-a-kind experiences, Chicago is home to more than 200 theaters, 200 art galleries and 7,300 restaurants. Our city also houses 26 miles of lakefront, 15 miles of bathing beaches, 36 annual parades, 19 miles of lakefront bicycle paths and 552 parks.

At Bobby’s Bike Hike, we pride ourselves on helping our customers enjoy the best our city has to offer. And we do that from the seat of a bicycle.

Because Chicago is so flat, it’s the perfect city to explore by bike. In fact, Chicago is ranked as the top city for biking in the United States. Chicago’s neighborhoods, parks and attractions are all connected by a network of trails and sidewalks that are ideal for exploring by foot or by bike. The best thing about exploring by bike is that you’ll not only see all the sights, but you’ll also hear the sounds, smell the pizza and experience firsthand the essence of what makes Chicago so great. For these reasons, we always recommend our out-of-town guests join one of our tours at the beginning of their trip. By experiencing Chicago in this manner, they can quickly become acclimated to the layout of the city and find plenty of other spots to return to later in their trip.

We can’t wait to share our favorite city with you. Contact us today to register for one of our Electric Bikes @ Night Tours and discover for yourself what makes Chicago so special.

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