Chicago
Luxury

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Our most recommended Chicago Luxury

Chicago: Brunch, Lunch, or Dinner River Cruise

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

Enjoy a fine dining experience on the Chicago River while admiring unparalleled riverfront views on this city cruise trip. Explore the beautiful Chicago Riverwalk when boarding the boat. Be welcomed aboard by the crew as the ship's photographer captures the moment. Arrive early for your cruise, dressed to impress. Be escorted to your table in the dining area. With its gorgeous glass-enclosed design, enjoy Chicago's incredible architecture from your seat. Savor a delicious meal prepared freshly on board. You can also buy a cocktail from the bar. To add to your enjoyment, the dinner cruise includes music by an onboard DJ. During the lunch and brunch cruises, listen to informative commentary on some of the architectural highlights along the river. On Wednesday and Saturday evenings throughout the summer, enjoy the Navy Pier fireworks display. Sample Dinner Menu Choice of starter: Caesar salad, lobster soup Choice of main course: Jumbo lump crab cakes, maple, and mustard glazed chicken breast, braised beef short rib, jumbo forest mushroom ravioli Choice of dessert: Eli’s original cheesecake, duo seasonal sorbet, chocolate decadent cake, odyssey signature warm butter cake Sample Brunch Menu Choice of starter: Caesar salad, Scottish smoked salmon toast, Greek yogurt, and granola parfait, fresh blueberries and strawberries Choice of main course: Cannellini bean shakshuka, maple, and mustard glazed chicken breast, scrambled eggs, raisin and cinnamon french toast Choice of dessert: Eli's New York-style cheesecake, tres con leche flan, triple chocolate mud pie, freshly cut fruit, and fresh strawberries Sample Lunch Menu Starter: Caesar SaladChoice of main course: Jumbo forest mushroom ravioli, maple, and mustard glazed chicken breast, oven-baked Atlantic salmon fillet, braised beef short ribChoice of dessert: Eli's New York-style cheesecake, freshly cut fruit, and fresh strawberries, duo of sorbet

Chicago: Downtown Chicago Helicopter Sightseeing Tour

2. Chicago: Downtown Chicago Helicopter Sightseeing Tour

Discover Chicago from above on this 15-minute helicopter tour. Capture pictures of stunning city views as you fly over downtown Chicago. View sights like Willis Tower, Shedd Aquarium, and Soldier’s field (home of the Bears). Check in at the tour supplier's centrally-located office in Chicago and get ready to take off with a company that is committed to a safety-first policy. Hop aboard a spacious and comfortable helicopter and experience the excitement of lifting off. Feel the thrill of flying north over the Chicago River and past downtown, before looping over iconic Wrigley Field and flying back south along the famous Chicago beaches and Navy Pier. Snap pictures above the Willis Tower, the Chicago River, Wrigley Field (home of the Cubs), Lincoln Park Zoo, Navy Pier, Shedd Aquarium, and Soldier’s field (home of the Bears). End your tour with a smooth landing.

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

3. 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

4. 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.

Frequently asked questions about Chicago Luxury

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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 101 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!

Beautiful activity, highly recommended. The rich food Attire is not so elegant. The only bad thing is that at times the air was very cold.

My daughter is special needs and they handled us with so much care! Will definitely come back if ever I visit Chicago again!

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

It was fabulous, the food, the music, the scenery, 100% recommended!!!