Top Chicago Dining Experiences

Make your evening in Chicago one to remember with this luxury sunset cruise featuring dinner, sightseeing and dancing along the shores of Lake Michigan. Feast your eyes on incredible views of iconic Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain and Soldier Field, then fill your belly with a bountiful all-you-can-eat buffet. Continue the celebration with a live DJ who will mix up a selection of dance favorites.

Take a gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago serving as your backdrop. Climb aboard your recently renovated vessel, featuring a sumptuously-appointed rooftop lounge and stylish interior design, for your cruise along Lake Michigan. Then sit down for a 3-course dinner, informed by some of the world’s top celebrity chefs and composed of fresh ingredients cooked right on-board. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks like the Willis (formerly Sears) Tower and Navy Pier, plus musical entertainment provided by the onboard DJ.

Enjoy a memorable, one-of-a-kind night out on Lake Michigan aboard this combination dinner, dancing, and sightseeing cruise. Make your own way to Navy Pier, and set off as the evening begins. You can admire views of Chicago’s picture-perfect skyline as the sun starts to set. While on board, take advantage of the all-you-can-eat buffet dinner, drinks to purchase, a DJ-helmed soundtrack, and even a fireworks display (weather permitting).

Cruise down the Chicago River in style during this 3-hour dinner cruise aboard the Odyssey. Watch the beautiful city and its architecture pass by through the ship’s panoramic windows. Then sit down to delicious 3-course meal accompanied by DJ entertainment to set the mood for your journey. A full-service bar complete with microbrews, creative cocktails, and a wine list is also available for purchase.

Travel down the Chicago River on an architecture cruise aboard the "Odyssey." As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch with salad, a main course such as chicken, salmon, pasta, or short ribs, and a dessert such as cheesecake or sorbet. Listen to onboard narration about the city's architecture along the way.

Valentine's Day is always a stressful time to find plans. Avoid the stress and book tickets to this Chicago Nitti's Supper Club Valentine's Day Show. This musical-comedy performance explores Chicago's gangster era with Broadway songs and top actors, too. Plus, you'll enjoy an included Valentine's Day dinner to combine dinner and a show.

When it's time to refuel in the Windy City, stop into Hard Rock Cafe Chicago for a tasty, filling, and enjoyable meal of classic American fare. Choose from a 2- or 3-course menu that's themed on musical styles all served with dessert and a drink. When ordering from this popular prix-fixe menu, entrees include salmon, steak, chicken, or a half-rack of hickory smoked ribs, and once you've enjoyed each succulent bite, stick around to explore the collection of music-themed memorabilia.

Learn the secrets of making one of Mexico’s most celebrated dishes during this beginner-friendly, local-hosted cooking class. Meet your Michelin-trained chef guide at her home, enjoy a refreshing hibiscus agua fresca upon arrival, and roll up your sleeves. Your guide will break down the steps to make an authentic mole sauce, and share tips as you go. Finally, sit down to enjoy your tasty and traditional meal.

Enjoy an unforgettable sky-high meal during this 2-hour Willis Tower dining experience at the Skydeck, an observation room situated high above Chicago's magnificent urban landscape. This 1,353-foot (412m) viewing area provides the magical setting for your evening, accompanied by a delicious Chicago-style deep dish pizza. Best of all, this special excursion offers VIP after-hours access to the Skydeck, ensuring the ultimate setting for that special occasion. Please see What to Expect section below for menu choices and enter your selections in the special requirements when booking.

Sample three different styles of pizza all in one day: this Chicago tasting tour offers a delicious way to explore. In the evening, meet your guide at the first restaurant, and be sure to come hungry—you’ll sample everything from the city’s iconic deep-dish pizza to Neapolitan and artisan slices. In between, meet the pizza makers and learn more about the Windy City’s culinary history.

Savor the flavors of Mexico’s Yucatan Peninsula, right in Chicago—and feel like a local when you dine in your host’s own home—during this small-group dinner experience. Be sure to come hungry: alongside a small group of diners, you’ll savor a multi-course menu of Yucatan classics, from a tropical starter to pibil tacos and beyond. In between, enjoy cocktails and the chance to converse with your host and fellow guests.

This is a very special and intimate gathering, celebrating anyones birthday, Anniversary, Bachelorette, Date night, or anyone celebrating visit to Chicago or anything at all! Guests will enter our intimate living space, with Spanish music. You will be enjoying a Spanish appetizer, a Spanish dinner all with homemade Sangria. As you finish dinner, you will enjoy a lecture/performance flamenco show with different styles or flamenco "palos"; through dance, sounds, melodies, feelings, emotions and all from our inner soul. Also, before finishing the show, we will combine a little class with a few steps. The experience includes hosting, beverage, dinner and performance.

This Mother’s Day, create family memories that will be treasured forever with an amazing Mother's Day Signature Dinner Cruise on Lake Michigan. While onboard, treat the mom in your life to a special night with our holiday buffet, classic cocktails, and Chicago's most incredible views. Celebrate with dining and dancing from our climate-controlled interior, or soak in the picturesque backdrop from our outdoor decks.

Wendella's Beer & BBQ Cruise is a world class Chicago experience for locals and visitors. Board our famous tour boats at Michigan Avenue, and enjoy the Chicago River and Lake Michigan while sampling a variety of craft beers from local breweries paired with authentic barbecue bites. A different brewery is featured each month. Enjoy these Chicago favorites while cruising Lake Michigan and the Chicago River. Must be 21+. There is also a full service bar and climate controlled cabin on the vessel's lower deck. This activity does not have a narrated tour but features light music during the cruise.

This Mother’s Day, create family memories that will be treasured forever with an amazing night on the water! Treat the mom in your life to a special Mother's Day Premier Dinner Cruise on Lake Michigan. While onboard, your family will enjoy chef-inspired, plated entrees with a selection of wine, Champagne, and classic cocktails. Celebrate with dining and dancing from our climate-controlled interior, or soak in the picturesque backdrop of Chicago's skyline from our outdoor decks. Start a new tradition the whole family will enjoy and celebrate Mother’s Day on the water!