Sitting on the shores of Lake Michigan, Chicago is one of the largest cities in the US, blending high-rise buildings, bold architecture, museums, culture, and art. It wouldn’t be a trip to Chicago without a visit to the Millennium Park, dining, and shopping at Navy Pier, or taking some Instagram-worthy photos on the 103rd floor of The Ledge at Skydeck. But, if we think of something that’s truly iconic to Chicago, that’s music. From blues and jazz to gospel, hip-hop, and indie, the city has long been the home of music. Here are the best places to enjoy live music in Chicago today.
1. Chicago fireworks buffet dinner cruise
A three-hour evening cruise on Lake Michigan is a great way to enjoy live music while admiring the beautiful Chicago skyline. You’ll get to enjoy a delicious dinner, listen to a live guide, watch a spectacular fireworks show, listen to live music, and dance to the sounds of Chicago’s best DJs under the stars. A buffet dinner, coffee, hot and iced tea, and gratuities are included. Alcoholic beverages are available for purchase. The cruise will pass by many famous city landmarks, including Soldier Field, Navy Pier, and Buckingham Fountain.
During the summer season, every Wednesday and Saturday, you can upgrade your cruise to include a spectacular firework display.
Book Tours : Chicago Buffet Dinner Cruise on Lake Michigan
2. Chicago brunch cruise on the Odyssey
A brunch cruise on the Odyssey will take you on a Lake Michigan tour, offering memorable views of the Chicago skyline, access to a lounge area on the observation deck, a buffet brunch, and great live music. The brunch menu will be freshly-prepared and include a variety of appetizers, entrees, salads, and desserts. The cruise will pass by many famous sights, including the Willis Tower, the Shedd Aquarium, the John Hancock, and Aon Center.
Book Tours : Chicago Premier Lake Michigan Brunch Cruise
3. Chicago cruise with buffet lunch
If you’re looking for a different lunch experience, this cruise is a perfect choice. Not only will you enjoy an extensive buffet lunch prepared daily by an Executive Chef, but you’ll get to enjoy lunch while cruising Lake Michigan, and take in the Chicago skyline views from the outdoor observation deck. You’ll get to hear the city’s story from an experienced guide, dance to the sounds of great live music, and enjoy a unique experience.
The cruise lasts for two hours and includes a buffet lunch, coffee, tea, and iced tea. Alcoholic beverages are not included in the cruise price but can be purchased there.
Guests should note that the dress code requires a dressy-casual attire and that smoking is not permitted indoors.
Book Tours : Spirit of Chicago Lunch Cruise
4. Private Chicago mafia and blues evening tour
Take a walk down history lane and learn about life in Chicago from the 1920s to 1940s, when it was all about blues music, mafia, sports teams, and city scandals. This private tour will take you on a historic sightseeing exploration that will end with a dive into the current nightlife scene. Your private guide will take you to the location of the St. Valentine’s Day Massacre, tell you about the Prohibition, how blues became a powerful force, and how the mafia got to expand and grow in Chicago.
End the two-and-a-half-hour tour by experiencing the modern-day nightlife scene, including a stop at Chicago’s landmark bar, previously owned by Al Capone. Enjoy a drink (for a fee) and live music, but make sure you have your ID with you.
Book Tours : Private Chicago Mafia and Blues Evening Tour
5. Chicago fireworks dinner cruise on the Odyssey
If you’d rather cruise the Odyssey at sunset, you can opt for the Chicago fireworks dinner cruise. Just like the name suggests, get ready to dine on board of the ship, watch a spectacular fireworks show, take in the Chicago skyline views in the sunset light, and dance the night away to the live band. After the Captain and crew greet you, the ship’s photographer will take a photo of you, and then you will be seated at your private table, where you’ll get to enjoy a three-course gourmet dinner.
The menu includes a tasting trio, entrees, and dessert. Coffee, tea, and iced tea are also included in the price, while alcoholic beverages are available for purchase. Guests are suggested to wear elegant attire, including jackets for men and cocktail apparel for women.
6. Chicago's premier music tour
Join a three-hour tour, and dive into Chicago’s music history for a chance to learn about the music genres that Chicago is famous for – blues, jazz, gospel, and rhythm and blues. The first part of the tour will be an open discussion about music history, while the second part is dedicated to the Rock N Roll history and how Chicago played a role in shaping this music genre. The tour begins at the Hyatt Regency, inside the main lobby and will take you through the streets of Southside Chicago, following the steps of big music names like Louis Armstrong, Mahalia Jackson, Curtis Mayfield, and many, many more. Continue the tour with a visit at the legendary Chess Records, and other iconic music venues, and join the group for a music-friendly challenge – “Name that tune or artist”.
Book Tours : Chicago's Premier Music Tour
Exploring Chicago with the sounds of music
The Windy City is not only one of the largest cities in the US or a place with spectacular architecture, but also a city that played a big part in the history of music. If you want to learn about Chicago’s music history and listen to some of the best live music, these tours are for you!
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