Chicago
Night Tours

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Our most recommended Chicago Night Tours

Chicago: 90-Minute Mob and Crime Bus Tour

1. 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 from a local expert tour guide giving interactive live commentary 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. You'll also view historic video footage, receive an informative pamphlet with photos, and can even take part in a crime quiz. Stake out crime scenes like the Biograph Theatre, Holy Name Cathedral, Clark Street Bridge, and other Chicago landmarks. See the site of the St. Valentine's Day Massacre, one of Chicago's most notorious murder scenes. Get off the bus and 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 Magnificent Mile neighborhoods.

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Chicago: 1.5-Hour Romantic Sunset Cruise

2. 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 get to admire the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. During your cruise, treat yourself at the full-service cash bar featuring authentic Chicago products. Try local beer and spirits and Garrett’s Popcorn. Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

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Chicago: Gangsters and Ghosts 2-Hour Walking Tour

3. 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.

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Chicago: Ghosts of Lincoln Park Walking Tour

4. 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.

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Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

5. 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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Chicago: Fireworks Premiere Dinner Cruise on Lake Michigan

6. 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 live music or relax on one of three climate controlled decks as you watch the lights of Chicago twinkling in the night. Don't forget to visit the Captains bridge, which is open during most of your cruise. Menu:  Tasting Trio Shrimp & Watermelon  English Cucumbers | Pickled Shallots | Extra Virgin Olive Oil Roasted Summer Vegetable SaladV  Yellow Corn | Zucchini | Caramelized Onions | Heirloom Tomato | Arugula | Herb Vinaigrette Whipped Goat Cheese  Candied Pecan Herb Crust | Balsamic Strawberries | Crostini Entrées Jumbo Lump Crab Cakes  Sweet Corn, Red Pepper & Thyme Succotash | Cajun Cream Sauce Oven Baked Atlantic Salmon Filet  Lemon Orzo with Red Onions & Sun-Dried Tomatoes | Citrus Dill Sauce Maple & Mustard Glazed Chicken Breast  Fingerling Potatoes & Chives | Haricot Verts | Dijon Mustard Cream Sauce Braised Beef Short Rib  Idaho Potato & Horseradish Mash | Baby Carrots | Pearl Onions | English Peas | Cabernet Sauvignon Sauce Greek Zucchini FrittersV  Lemon Orzo with Red Onions & Sun-Dried Tomatoes | Spring Onion & Cucumber Tzatziki Desserts Duo of Sorbet  Seasonal Sorbet | Fresh Fruit Granny Smith Apple Parfait  Cinnamon Spiced Apples | Almond & Oat Crumble | Candied Chili Bacon Salted Caramel Cake  Dark Chocolate Ganache | Raspberry Sauce Odyssey Signature Warm Butter Cake  Vanilla Bean Ice Cream | Blackberry Sauce Menu subject to change without notice.

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Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan

7. Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan

Enjoy a summer or autumn evening on this Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan. This popular 60-minute narrated tour ensures you have the best views of this magnificent fireworks display. Every seat on the Seadog Speedboat Fireworks Cruise has amazing panoramic views of Chicago's historical skyline. Whether you are looking for a romantic evening, a night out with friends, or simply appreciate the art of pyrotechnics, this tour will have everyone of all ages leaving with a smile. Come and visit all of the possibilities that Chicago has to offer by enjoying a magical Fireworks Cruise on Lake Michigan. These memories are made to last a lifetime!

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

8. 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 Riverwalk, with the knowledge that you can continue exploring the city with confidence. From the pioneering skyscrapers, to the Great Chicago Fire, this night tour will take you on a journey you won't soon forget. Be sure to soak up the exciting atmosphere that makes the Windy City such a fascinating and dynamic place.

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Chicago Crimes Night Tour

9. 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 Magnificent Mile neighborhoods.

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Chicago: Private 3-Hour Al Capone Gangster Tour

10. Chicago: Private 3-Hour Al Capone Gangster Tour

Experience amazing stories of true crime coming to life on this three-hour private tour. Visit many of the old venues where gangsters used to operate, including old speakeasies and historic hotels. Your expert historian guide will accompany you and your private group in luxury accommodation to historically significant locations in the city. View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, and the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy guns. See the site of the infamous St. Valentine’s Day Massacre, and sit in Al Capone’s booth at the Green Mill. Finally, visit the location where Public Enemy #1 John Dillinger was assassinated by the FBI.

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

4.4 / 5

based on 304 reviews

Kai was an excellent guide for our activity last night. She had so much knowledge of Chicago history and when we requested more of history/ gangster knowledge vs just the speak easy stops, she made a significant pivot to make our activity specific to our requests. Would highly recommend this tour and Kai!

Our tour guide, Lizzy, was amazing! She was extremely knowledgeable and told us all of the interesting facts! Highly recommend!

Learned some new things, like the sinking in the Chicago River.

Kai knew her facts, quite entertaining yet informative.

Our guide was amazing, so knowledgeable & friendly.