Chicago
Night Tours

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Our most recommended Chicago Night Tours

  • Chicago: 1.5-Hour Romantic Sunset Cruise

    1. Chicago: 1.5-Hour Romantic Sunset Cruise

    Start your sunset cruise on the Chicago River at Michigan Avenue. Make your way along the main branch of the river towards Lake Michigan before entering the Chicago Locks, a modern engineering marvel, that will transfer the vessel onto the great Lake Michigan. The vessel will cruise along Lake Michigan as the sun sets behind the wonderful skyline offering several amazing views. Your local tour guide will give a very brief commentary along the Chicago River and entrance to Lake Michigan, but most of the 1.5-hour cruise is spent without narration, leaving you to watch the sun put on a beautiful display with the City skyline. Admire the many angles of the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Capture magical views of Chicago's twin super-skyscrapers, the famous Willis (formerly Sears) Tower and the John Hancock Building. You'll also ge...

    It was the best price for a river tour and I know sometimes if you pay less you get less but this star was outstanding. I would highly recommend

  • Chicago: Gangsters and Ghosts 2-Hour Walking Tour

    2. Chicago: Gangsters and Ghosts 2-Hour Walking Tour

    See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with interesting stories hidden behind each turn.

    Embark along the Chicago Loop, known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone used to party, make deals, and carry out business.

    Visit haunted locations and old crime scenes led by historians. Stop at the Congress Hotel, Death Alley, and the Palmer House. Enjoy a refreshment along with way, with frequent stops and a restroom break.

    We loved this tour, Stephan was very funny and knowledgeable. Will suggest to friends and family:)

  • Chicago: 90-Minute Mob and Crime Bus Tour

    3. Chicago: 90-Minute Mob and Crime Bus Tour

    Experience Chicago’s underworld of criminals and gangsters on a luxury 90-minute bus tour. Find out how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the city. Ride comfortably in luxury, on a climate-controlled bus, as you see famous Chicago crime scenes that range from the 19th century through modern times. Unlike Chicago walking tours, this Mob and Crime Tour isn’t affected by the Windy City weather. Learn about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, Terrible Tommy O'Connor, H. H. Holmes, the Chicago Black Sox, Leopold and Loeb, bank heists, Cap George Streeter, and more. Grab your camera for a drive-by shooting of the historic criminal courthouse, a Chicago architectural landmark where some of Chicago's most notorious cases were tried. Stake out crime scenes like the Biograph Theatre, Holy Name Cathedral, Clark ...

    Our guide was great and very informative. His dad jokes were pretty on point too.

  • Chicago: 90-Minute River and Lakefront Cruise at Night

    4. Chicago: 90-Minute River and Lakefront Cruise at Night

    Experience the magic of Chicago at nighttime and watch the city's glorious skyscrapers, historic buildings and modern marvels come to life with millions of twinkling lights. Relax and unwind at the end of the day on a cruise which not only lets you enjoy the scenic Chicago River, but also takes you through the Chicago Harbor Lock and out onto Lake Michigan where you can admire epic views of the sparkling Chicago skyline and shoreline. Throughout the ride, listen to lively narration about Chicago's rich history as the onboard guides point out the many sights of the city including Buckingham Fountain, Willis Tower, Aon Center, John Hancock Building, Museum Campus, Marina City, Wrigley Building, Chicago Tribune Building, Navy Pier, the Lighthouse and more. This tour also gives you the unique experience of passing through the Chicago River Lock System, while learning about the operation an...

    Great activity and perfect timing on the fireworks. The only improvement I would suggest is an expanded food menu.

  • Chicago: Ghosts of Lincoln Park Walking Tour

    5. Chicago: Ghosts of Lincoln Park Walking Tour

    Meet your guide at the meeting point then set off on an unforgettable walking tour through Northside Chicago. Travel back in time as you visit some of the city’s most haunted locations in the mysterious Lincoln Park neighborhood. Learn about the forgotten burial ground that forms the foundation of this bustling district. Check out the bathroom mirrors at Lincoln Park Zoo, home to the ghost of a Victorian woman in white. And, hear about the spirit that haunted Al Capone in his final days.  Throughout the tour, you’ll listen to the strange and disturbing tales of each location. On the standard tour, visit eight historic sites, or opt for the extended tour which includes 12 ghoulish locations. By the end of the tour you’ll have learned about and experienced firsthand the alternative side of Chicago.

    Tammie was an excellent guide, engaging and full of interesting stories. Other people on the tour squealed with delight as she told them tales of ghosts. Also some great history thrown in!!

  • Chicago: 1.5-Hour Open-Top Double-Decker Night Tour

    6. Chicago: 1.5-Hour Open-Top Double-Decker Night Tour

    From the top deck of a double-decker bus, experience Chicago at night. Enjoy a 75-minute, live-guided panoramic tour and take in unique views of the Chicago Skyline, comprised of world-famous skyscrapers and revolutionary architecture. Take a photo overlooking downtown from the Museum Campus in front of the Adler Planetarium. Be amazed by the beautiful water and light display of The Buckingham Fountain as you discover the bustling nightlife of Chicago. Marvel at the magical light show of the one-of-a-kind Art on the Mart, displayed on the facade of the Merchandise Mart. See the city reflect off of The Bean (Cloud Gate) at the famous Millennium Park. Experience the city that built the skyscraper and see architectural marvels like 875 N Michigan Ave (formally the John Hancock Building), the Wrigley Building, the Chicago Tribune Building, and the Willis Tower. End the tour at the Chicago ...

    It was awesome, although we didn't get the complimentary popcorn? People were saving sets for others that were LATE causing others to not get sets up top.

  • Chicago Fireworks Buffet Dinner Cruise

    7. Chicago Fireworks Buffet Dinner Cruise

    Quite simply, a Spirit dinner cruise is the perfect night out. A magical setting enhanced by dazzling city sights and Lakefront lights. An evening filled to the brim with wonderful cuisine, live music, dancing under a canopy of stars and a spectacular fireworks display over the Chicago skyline. This three-hour dinner cruise this is the ultimate Chicago experience. Menu:  Salads: Organic Mixed Field Greens  Grape Tomatoes | English Cucumbers | Carrots | Corn | Kidney Beans | American Cheddar Cheese | Herb Croutons | House-Made Ranch Dressing | Balsamic Vinaigrette | Low-Fat Italian Dressing Organic Spinach & Kale Salad  Aged Reggiano Parmesan Cheese | Red Bell Peppers | Red Onions | Lemon & Oregano Dressing Roasted Red Beet Salad  Pickled Shallots | Fresh Mint | Italian Parsley Mediterranean Couscous & Chickpea Salad  Scallions | Plum Tomatoes ...

  • Chicago Crimes Night Tour

    8. Chicago Crimes Night Tour

    Uncover how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the Windy City. Ride in luxury on a climate-controlled bus, as you explore famous Chicago crime scenes ranging from the 19th century through to modern times. Learn about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, The Lady in Red, Captain George Streeter, Frank "The Enforcer" Nitti, Bugs Moran, Johnny Torrio and more. Grab your camera for a drive-by shooting of historic and architectural landmarks, and stake out crime scenes like the Biograph Theatre, Holy Name Cathedral and St. Valentine's Day Massacre, one of Chicago's most notorious murder sites. Walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnif...

    John was our guide and he was so much fun to have leading us through the whole thing! He’s very knowledgeable and made the whole experience fun & interesting! Highly recommend trying this out!

  • Chicago Fireworks Premiere Dinner Cruise on Lake Michigan

    9. Chicago Fireworks Premiere Dinner Cruise on Lake Michigan

    Dine aboard our unique boat, the Odyssey, which is designed to provide the ultimate viewing of Chicago's sights. Dine on a gourmet three course meal served at your private table, then dance the night away to the live band and watch the beautiful fireworks display with the Chicago skyline as a backdrop. Experience an elegant dining cruise along the Chicago shoreline aboard the luxury cruising vessel, Odyssey. Your evening starts as you are greeted aboard by the Captain and crew and our ship's photographer will take a picture to capture your memory. After being seated at your private table, enjoy your gourmet three-course meal consisting of creative appetizers and entrees prepared fresh onboard daily by our Executive Chef. The wait staff will time your meal according to your preferences so you can savor every moment of your three hour dinner cruise. After dinner dance to the li...

  • Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

    10. Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

    Spend an evening visiting the Chicago speakeasies that have been open since the Prohibition Era in the 1920s, many preserved in their original conditions. With your own private group, enter by way of secret entrances and enjoy the same cocktails ordered by infamous Chicago gangsters and bank robbers at these venues nearly a century ago. Relive the glamor of the 1920s while listening to stories of the rampant racketeering and bootlegging of the era.   Alcohol is available for purchase at the three to four different speakeasy stops. Your private tour guide will make Prohibition Era drink recommendations and tell you the stories behind them. Travel around with your young, professional guide and be chauffeured in luxury transportation, ranging from a luxury SUV to a full-sized luxury motor coach.

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What people are saying about Chicago

Overall rating

4.4 / 5

based on 304 reviews

Amazing and beautiful scenery while on the tour!! To see the beautiful Chicago Skyline as the sun set, was pleasing to my eyes. The tour guide was quite entertaining, which was an added bonus in the learning of Chicago's History. The tour was definitely worth taking!!

It was the best price for a river tour and I know sometimes if you pay less you get less but this star was outstanding. I would highly recommend

Our guide was great and very informative. His dad jokes were pretty on point too.

Wonderfully interesting, engaging guide who kept the group wanting more.

Was an incredible experience!!! I love ❤️ The Windy City