Chicago is a city of two waterfronts. Both Lake Michigan and the Chicago River offer stunning views of the city skyline, especially at night when Chicago’s most iconic buildings are all lit up. And there’s no better way to experience these breathtaking vistas than on a dinner cruise. Chicago has plenty of options, from sit-down fine dining to casual buffet style. Dine with skyline views on Chicago’s unforgettable dinner cruises.

Odyssey Chicago River

People dining on Odyssey River Cruise with Chicago views

Odyssey is the first cruise line in the city to offer dining cruises along the Chicago River with their Odyssey Chicago River cruise. Dinner is served on their state-of-the-art, European-styled, glass-enclosed vessel — think 360-degree views of the surrounding cityscape.

The experience offers an elegant, white tablecloth dinner while you gaze up at Chicago’s incredible architecture. An onboard DJ and dance floor adds to the fun. The single-level vessel includes outdoor decks and a climate-controlled interior for year-round cruising. Docking space on the north side of the Chicago River lands you mere steps from Michigan Avenue and The Magnificent Mile.

Odyssey Lake Michigan

The atmosphere on Odyssey Lake Michigan is magical. You’ll be dining aboard an elegant tri-deck yacht with an outdoor observation deck where you can watch the sun set over the waters of Lake Michigan. During the summer, opt for a fireworks cruise on Wednesday or Saturday evening for an even more unbelievable view.

If you can pull yourself away from the skyline, you can enjoy a freshly prepared, three-course meal. Enjoy wine, beer, and cocktails from the cash bar. For special occasions, you can enhance your meal with add-ons like jumbo shrimp cocktail, a seafood tower, or lobster tail. Just make sure to reserve a window table for the best view.

Tip: The decks are climate-controlled, so cruises depart year-round. Check out Odyssey’s holiday cruises, like an unforgettable New Year’s Eve dinner.

Mystic Blue Dinner Cruises

Couple enjoying dinner on a Mystic Blue cruise in Chicago

If you’re after a cool and casual vibe, then Mystic Blue is for you. The feel on these lakefront dinner cruises is more of a high-energy party, with comfortable, stylish attire encouraged. Fill up your plate from the seasonal dinner buffet (stocked with veggies, pasta, fish, chicken, dessert, and more), then hit the dance floor helmed by a live DJ spinning the latest hits.

Mystic Blue also offers cocktails, wine, and beer at its cash bar, the option of a guaranteed table for your party size, window tables for the best views, and additional upgrades to customize your experience. Best of all, Mystic Blue’s cabins are climate controlled for year-round cruising.

Tip: In the summer, fireworks are launched off Navy Pier each Wednesday and Saturday evening. Catch a Mystic Blue fireworks cruise to see all the action from the water.

Spirit of Chicago

Couple sharing a drink on A Spirit of Chicago dinner cruise on Lake Michigan

A romantic date, a fun night with friends, a birthday, or special occasion. Spirit of Chicago is the perfect dinner destination for any occasion. Over the course of the night, you’ll dine, dance, and see some of Chicago’s most iconic landmarks (like Navy Pier, Buckingham Fountain, and Willis Tower) from the scenic waters of Lake Michigan.

Everyone in your group will find something at the buffet, which is loaded with freshly prepared dishes made with seasonal ingredients. Plus, there’s loads of onboard entertainment, from a live DJ and dance floor to group games like giant Jenga and shuffleboard. Add extras like drinks from the well-stocked cash bar, a window table, and more. Cruises depart from Navy Pier all year long.