Chicago
Luxury

Enter your dates to find available activities

Our most recommended Chicago Luxury

  • Chicago River: Brunch, Lunch, or Dinner City Cruise

    1. Chicago River: Brunch, Lunch, or Dinner City Cruise

    Admire the unparalleled riverfront views as you enjoy a fine dining experience on the Chicago River. Arrive early for your 2-hour cruise, dressed to impress. Explore the beautiful Chicago Riverwalk when boarding the boat. The crew will welcome you aboard, and the ship's photographer will record the moment. You'll be escorted to your table in the dining area. With its gorgeous glass-enclosed design, you can enjoy Chicago's incredible architecture from your seat. Savor a delicious meal prepared freshly onboard, and choose to buy a cocktail from the bar.   To add to your enjoyment, the dinner cruise includes music provided by an onboard DJ. During the lunch and brunch cruises, occasional onboard narration will be provided about some of the architectural highlights along the river. On Wednesday and Saturday evenings throughout the summer, you'll have amazing views of the Navy Pier firewor...

    Beautiful time and wonderful staff. Well worth the money spent, will definitely book again soon!

  • Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

    2. 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.

  • Chicago: Private 3-Hour Al Capone Gangster Tour

    3. 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.

Other Sightseeing Options in Chicago

Want to discover all there is to do in Chicago? Click here for a full list.

What people are saying about Chicago

Overall rating

4.4 / 5

based on 101 reviews

Food is excellent!!!! I was running late and they still allowed me on! I would most definitely come here again and worth every single penny. A must do!

The best good and service on a lunch cruise. The European style river craft was great! Views all around and up!!!

Beautiful time and wonderful staff. Well worth the money spent, will definitely book again soon!

We sailed around the city, and was introduced to the Chicago skyline, and architecture.

Awesome Cruise! Relaxing very scenic and the food was delicious!