There are literally a ton of things you can do when you’re visiting Chicago. There are architecture tours, air and helicopter tours, museums and exhibitions, shows and musicals, festivals galore (both for art and for music), family-friendly activities, things to do at sunrise and at sunset, and everything else in between.

Perhaps the most memorable experience you will have is joining a signature dinner cruise that runs from Navy Pier. These cruises typically last between two and three hours, have DJs on board to entertain you with some much-loved songs, you’ll get to see the Chicago skyline, and overall have a swell time aboard with your friends, family, colleagues, and loved ones. But which sunset cruise should you opt for? We explore a few of them so that you can make the best choice for you.

Odyssey Chicago River

Odyssey is renowned for being the first cruise line in Chicago to offer guests dining cruises along the Chicago River. The Odyssey Chicago River cruise serves dinner on a state-of-the-art, European-styled, glass-enclosed vessel. The beauty of all this is that you will be able to enjoy 360-degree views of the surrounding cityscape and amazing architecture. Offering an elegant experience, you’ll also enjoy a white tablecloth dinner. Fun is added to the mix with an onboard DJ. This is a single-level vessel that includes both outdoor decks and air conditioned interior for all-year-round cruising. Because the docking space is just on the north side of the Chicago River, this means you’re literally a few steps away from Michigan Avenue and The Magnificent Mile.

Odyssey Lake Michigan

Odyssey Lake Michigan offers guests an unforgettable experience. When aboard the elegant tri-deck yacht with an outdoor observation deck, you will enjoy a freshly prepared three-course meal. There are also beers, wine, and cocktails at the cash bar. And for very special occasions, you can boost your meal with add-ons including jumbo shrimp cocktail, a seafood tower, or lobster tail. For the best views, make sure you reserve a window table. And for an even more magical experience after watching the sunset, you can take up the fireworks cruise on Wednesday or Saturday evenings. This will add to the sophisticated touch of this cruise and you’ll make amazing memories.

Mystic Blue Dinner Cruises

Mystic Blue offers guests on board a less formal vibe, opting more for the cool and casual. Some describe these cruises as a “high-energy party” although it is encouraged that you dress comfortably yet stylishly. For dinner, you can enjoy a delicious seasonal buffet which is packed with vegetables, pasta, fish, chicken, desserts, and more). Once you’ve had your fill, you can get onto the dance floor that is led by a live DJ playing the latest hits. For drinks, you can enjoy a variety of alcoholic beverages at the cash bar. In addition to all this, the boat’s cabins are air conditioned, making for comfortable all-year-round cruising.

Spirit of Chicago

Whether you’re coming from out of town and want to have a memorable night in Chicago or you live in the city but want to look at it from a different perspective, the Spirit of Chicago offers a romantic, fun experience for everyone involved. Described as the “perfect dinner destination for any occasion”, you’ll be able to enjoy a lovely meal at dinner time, move your body to some smashing hits, see some of the most iconic sights of Chicago all this from the incredible location of being on Lake Michigan. The buffet offers freshly made meals with seasonal ingredients. You can also enjoy games like Jenga and shuffleboard. For alcoholic beverages, don’t hesitate to hit the cash bar. And for the most memorable experience, don’t forget to book a window-side table. These cruises depart from Navy Pier throughout the year, so it doesn’t matter when you find yourself there – you’ll simply have a blast.


Tall Ship Windy

And finally, for those who want the real pirate experience and to roll your sleeves up as the cruise gets sailing, you can help the captain and crew with raising the sail of this incredible vessel and have a night out that will be unforgettable. These sails are both fun and educational, which makes them the perfect way to see Lake Michigan. But what’s more is that Tall Ship Windy offers the most spectacular fireworks experience during the Chicago summer, which are held every Wednesday and Saturday on the shore. Experiencing the breathtaking views from the water is simply magical. Watching the Chicago skyline as the sunsets will add onto this incredible adventure. All while you enjoy deliciously prepared food and a fun night out.

Wrapping up

Ready to hit the water as you embark on your Chicago dinner cruise journey? What better way to ensure your entire trip is as perfect as possible than with the best transportation partner in town? With Bus Connection, you’ll always arrive at your destination on time, every time, all while traveling in comfort and style. We treat each of our passengers as special guests and ensure you have the most memorable experience. Don’t hesitate to get in touch with us for more information. We’re just a click away.