Top Things To Do in Chicago at Night

Explore the Windy City - the third largest city in the United States, known for its Chicago-style (deep dish) pizza and hot dogs, 1920’s gangsters like Al Capone, and its stunningly unique architecture. Witness the bustling urban city brimming with things to do at night - in a city as large and magical as Chicago there is certainly no shortage of nighttime activities!

Take a Chicago Night Tour

Tripshepherd - Scenic Chicago Night Tour

Immerse yourself in Chicago’s distinct skyline with bold skyscrapers and incredible views of Lake Michigan illuminated at night. Begin your 3-hour small-group Scenic Night Tour of Chicago with complimentary downtown Chicago hotel pick-up in the comfort and style of one of our Mercedes Metris vans.No trip to Chicago is complete without a visit to the top of the tallest building in the Western Hemisphere - Willis Tower (formerly Sears Tower). Taking the elevator all the way up to the 103rd floor where you will enjoy a dazzling 360-degree view spanning 50 miles and 4 states.

The most spectacular view - 1,353 feet down "Dare to Stand Out" on The Ledge (360 Chicago) - special glass balconies extending 4.3 feet outside the building which provides a thrilling, once-in-a-lifetime experience. Once your feet are back on the solid ground your guide will take you on a beautiful skyline cruise to see the beauty of Chicago's architecture lit up by the moonlight and bustling city lights, witnessing world-famous skyscrapers from the Chicago River. Aboard the relaxing cruise, you will enjoy a narrated boat tour where you will see the breathtaking views of over 40 Chicago iconic landmarks, from hidden architectural features to the Windy City's most famous monuments.

To end your night out, immerse your senses in a spectacular light and music major display at Buckingham Fountain - one of the largest fountains in the world. You will also get to see the infamous Chicago Bean (also known as Cloud Gate), British Anish Kapoor’s first public outdoor work installed in the United States. At the end of your tour, your guide will take you back to your downtown Chicago hotel.

Gangsters and Ghosts Tours In Chicago

Join Chicago Gangsters and Ghosts Tours on a 2-hour history lesson with supernatural tales. Step back in time and learn about the Windy City in the roaring 1920’s when speakeasies attracted notorious bootleggers and gangsters, visiting their former hangouts. Get spooked at one of the city’s haunted places such as Congress Hotel, Palmer House, and Death Alley.You can also join Chicago Crime Tours and Experiences on their 120-150 minute guided nighttime crime history tour featuring some of the city’s top crime sites along with other Chicago landmarks.

Big Bus Chicago Night Tour

Hop on a guided bus tour, led by BigBus Chicago on a 75-minute nighttime tour. Explore the Windy City witnessing the city’s dazzling skyscrapers including visits to the Navy Pier, Magnificent Mile, Museum Campus, and other famous landmarks.

2-Hour Chicago City Lights Evening Segway Tour

Join Absolutely Chicago Segway Tours to witness the city like never before. Visit popular spots such as Grant Park, and Buckingham Fountain’s evening light show all illuminated at night. You will take in views of the Field Museum of Natural History, Shedd Aquarium, Soldier Field, and Michigan Avenue.

Private Evening Sail in Chicago Ending with Navy Pier Fireworks

Treat yourself to a luxurious private sailboat cruise where you will sail around the beautiful lakefront to view the city skyline, on this tour you will get the perfect vantage point to enjoy the incredible fireworks display put on by Navy Pier.

Along the tour, you will get a chance to pass landmarks such as Buckingham Fountain, Shedd Aquarium, Adler Planetarium, Soldier Field, and Navy Pier.

Take a Stroll Under the Stars

Escape the busy hustle and bustle of the downtown core or attractions and take a night stroll under the stars in one of the city’s beautiful parks.

Grant Park

Grant Park also known as “Chicago’s front yard” is a large urban park in the Loop community area within the central business district that features Millennium Park, Buckingham Fountain, and the Art Institute of Chicago. This beautiful green space features several gardens and flower displays including the Lurie Garden known for its tall grass flowers particularly lavender and a decorative post-modern water stream.

On the northeast side of the park, there is the Richard & Annette Bloch Cancer Survivors Garden marked by two huge doric columns left from the demolished Chicago Federal Building and contains walkways lined with planters. The park also houses the Court of the Presidents, well-maintained gardens, and artwork showcasing work by Chicagoans and the Chicago Lakefront Trail.

The trail offers an 18-mile multi-use path along Lake Michigan's shoreline running through the park's eastern edge.

Chicago Riverwalk

Chicago Riverwalk is another great place to enjoy a scenic nighttime stroll along the water's edge including stunning outdoor bars and restaurants, museums, pier fishing, boat trips, kayaking, public art, and bird-watching.

Navy Pier

If you are looking for a picturesque waterfront nighttime trail, enjoy the Navy Pier the place to go for events, free public programs, attractions, culture, dining, shopping, and more! The area features a VIP Private Gondola Ride on the Centennial Wheel, Chicago Shakespeare Theater, Chicago’s Children Museum, Light Up the Lake, Virtual Rush: Chicago, and Tall Ship Windy.

At the navy pier, you can also board City Cruises or Shoreline Sightseeing to view the stunning and unique Chicago skyline architecture illuminated at night.

Immerse Yourself in History and Culture at one of the city’s Museums

Field Museum

Learn about the Egyptian mummies, and the man-eating lions of Tsavo, and explore the largest and most complete Tyrannosaurus rex ever discovered at the Field Museum of Natural History - one of the largest museums in the world.

This massive natural history museum includes more than 30 permanent exhibitions covering a whopping 480,000 square feet.

Shedd Aquarium

Shedd Aquarium boasts several permanent exhibits connecting nature lovers and animal enthusiasts with the aquatic world animal world. Here, guests will visit 1,500 species including fish, marine mammals, birds, snakes, amphibians, and insects in their exhibits.

Their exhibits include; the Waters of the World (featuring aquatic animals such as seahorses and the blue iguana, etc.,), Caribbean Reef (home to stingrays, green sea turtles, and bonnethead sharks), Amazon Rising (red-bellied piranhas, eels, green anacondas, etc,.), Wild Reef (blacktip reef shark coral, etc,.), Oceanarium featuring marine mammals such as the beluga whale and sea lions and One World.

The aquarium also features exhibits like the Polar Play Zone featuring a starfish touch pool, the Stingray Touch tank, and the 4D Theatre where guests can watch a 3D film in interactive seats with high-tech audio and interactive elements.

Art Institute of Chicago

One of the city’s most well-known cultural buildings due to the iconic pair of bronze lions at the entrance’s grand steps - the Art Institute of Chicago encompasses almost 300,000 artworks. Some iconic pieces of art include; Georges Seurat’s A Sunday on La Grande Jette - as seen in Ferris Bueller’s Day Off as well as traveling exhibits focusing on Andy Warhol and Van Gogh.

Adler Planetarium

Explore America’s very first planetarium and a premier resource for inspiring the next generation of space explorers at the Adler Planetarium. The public museum offers guests a variety of exhibits including their newest - Chicago’s Night Sky an exhibit exploring the human tradition of looking up through artwork and astronomical objects while raising awareness about light pollution and protecting our dark skies.

You can also explore our planets with their exhibit Our Solar System featuring large models of Saturn, Jupiter, Neptune, and Uranus hanging from the ceiling - providing great selfie opportunities.

Take in the city’s stunning architecture while standing at the huge sundial in front of the museum and witness the best and most comprehensive sundial collection in all of North America.

Catch a Chicago Clubs Night Game at Wrigley Field

Root for the home team at the home of Chicago Cubs - Wrigley Field.Wrigley Field, located on the North Side and a designated National Historic Landmark (2020). First opened in 1914, the field is known for its ivy-covered brick outfield wall, the iconic red marquee over the main entrance, the hand-turned scoreboard and for being the last Major League park to have lights installed for night games.

This world-renowned stadium is not only used for baseball games but also houses several other sports and events such as football, soccer, hockey, and concerts. Wrigley was the first Major league ballpark to introduce live organ music in 1941 and is also where the tradition of singing “Take Me Out to the Ball Game” at Cubs home games began.

Explore the Magnificent Mile

Chicago’s Magnificent Mile is packed with things to do and see including the city’s best attractions along with more than 50 historic landmarks. Here, you can check out the scenic skyline and iconic architecture 150 feet in the air on the new Ferris Wheel at Navy Pier. Look out at views in all directions from 1,000 feet above The Magnificent Mile at 360 Chicago, enjoy the entertaining nightlife with friends downtown, or learn more about the city’s history in sports at the Chicago History Museum. 

Tripshepherd Fun Fact: Until March 27th, 2022 you can enjoy the Office Experience where you can visit the Dunder Mifflin set, Schrute Farms, and relive Jim and Pam’s whirlwind romance including original show costumes & props, set recreations, and opportunities to engage with the show.

Catch a Show at the Iconic Chicago Theater

Originally known as the Balaban and Katz Chicago Theatre, the Chicago Theatre is a landmark located in the Loop area of Chicago. Built-in 1921 by A.J. Balaban and his brother Barney, it was a dominant movie theatre enterprise from 1925 to 1945.

Owned and operated by Madison Square Garden Inc the theatre is now a performing arts venue for stage plays, magic shows, comedy, speeches, sporting events, and popular concerts.

The building was added to the National Register of Historic Places in 1979 and a Chicago Landmark in 1983 and its distinctive theatre marquee serves as an unofficial emblem of the city appearing frequently in film, artwork, and photography.

Whether you are exploring during the day or at night, traveling with family, or enjoying the famous nightlife, the infectious positive energy of the Windy City will make it a trip to remember.