Top Chicago Likely To Sell Out in 2026

Get to grips with Italian pasta in this Florentine-inspired hands-on class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs. Carpaccio, hand-filled ravioli, a fresh vodka sauce and citrus cookies – four courses, four distinct techniques, one deeply satisfying Italian meal. Your hands-on cooking experience features: - Marinated Vegetable Carpaccio – assorted vegetables, homemade herb dressing and fresh herbs - Beef Ravioli – flour, eggs and seasoned beef - Vodka Sauce – olive oil, tomatoes and vodka - Italian Lemon Drop Cookies – flour, butter and eggs You will leave with real pasta-making skills and a fresh perspective on Italian cuisine, from antipasto to dessert. Guests are welcome to bring wine or beer to enjoy throughout the experience.

Glide through Chicago by moonlight on a haunted Segway tour. Follow your costumed guide and small group as they show you the sites of some of the most gruesome murders and disasters in Chicago's history. See iconic landmarks lit up at night and hear about the mysterious, haunted history of this storied city.

Discover the unique flavor of our Absolutely Chicago E-Bike Tour. Experience the city's rich history, stunning architecture, and breathtaking views as you pedal along on our state-of-the-art electric bikes. From iconic landmarks to hidden gems, this unforgettable adventure combines adventure, warmth, and loads of fun. Immerse yourself in the vibrant atmosphere of Milton Olive Park, the wonder of Soldier Field, and capture unforgettable photos at the majestic Buckingham Fountain. With flexible routes and a focus on hidden treasures, our tour offers a truly unique and memorable experience through the heart of Chicago.

Enjoy an only-in-Chicago night out—and admire views of the city's skyline and evening fireworks shows that most visitors miss—on this Lake Michigan cruise. Make your own way to the departure point at Navy Pier, hop aboard your well-appointed vessel, and set sail. In between marveling at the views, you can purchase drinks and snacks from the on-board cash bar, if you wish.

Enjoy a new perspective on the Windy City—and see more of its sights in less time, all without breaking a sweat—on this small-group, sunset Segway tour. With included instruction and hands-on guidance, get comfortable on your Segway in no time. Then, set off to discover top Chicago highlights from the Museum Campus and Millennium Park to Buckingham Fountain and beyond, all while the city's lights slowly come on.

This is truly an experience like none other. It is combination of a historical walking tour of the Chicago Riverwalk and Yoga. It is a very non-traditional Yoga experience as we incorporate flows along the walking tour, in picturesque locations with beautiful views. No mats are necessary as we incorporate the surrounding elements of the Riverwalk, ie: benches, steps, and grassy lawns. A Fit Tour is the most unique way to "get your steps in" and actively engage with the surrounding city.

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This 2.5 hour small group (12 Guest Maximum) guided walking tour is perfect for busy sidewalks and getting up close to monumental art! Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”

Fresh, vibrant and built on ingredients you can find anywhere – this Mediterranean cooking class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs, teaches three crowd-pleasing dishes that bring the coast straight to your kitchen. Your hands-on cooking experience features: - Hummus with chickpeas, lemon, cumin and olive oil - Greek Chicken With Lemon and Feta with chicken breast, Feta, thyme, lemon and white wine - Balsamic Berries With Greek Yogurt with Greek yogurt, honey, balsamic vinegar and mixed berries You will leave ready to recreate a full Mediterranean spread at home – from hummus to dessert. Guests are welcome to bring wine or beer to enjoy throughout the experience.

Enjoy a hassle-free day trip to one of the Midwest’s highlight cities—and leave all the planning and transit logistics to someone else—on this full-day excursion from Chicago to Milwaukee. Upon arriving in Wisconsin’s biggest city, visit the Harley-Davidson Museum, Public Market, the Milwaukee Art Museum, and more (lunch and admission tickets additional expense). Or, in autumn, choose to enjoy a separate foliage-themed itinerary.

Admire views of the Windy City that few other visitors get to experience—and enjoy an efficient way to sightsee—with this small-group helicopter flight. Make your own way to the heliport, meet your pilot, and get settled aboard. Then, take to the skies to admire aerial views of sights ranging from Navy Pier and the Museum Campus to the Willis Tower, Lake Michigan shoreline, and much more.

Join our exclusive cooking workshop series in collaboration with celebrity chef Tony Hu. In the first session, you'll learn to prepare two of his signature dishes—Chef’s Special Dry Chili Chicken and Crispy Lemon Shrimp. Featured on numerous TV shows and interviews, including NBC, ABC, FOX, and WGN, Chef Tony Hu is the founder of the iconic Lao Sze Chuan Restaurants with 14 locations across the country. This hands-on cooking workshop is more than just a culinary lesson—it’s a cultural experience. We invite you to connect with Chinese heritage in a warm, interactive setting where every dish tells a story, and every bite is a celebration of tradition. A minimum of 4 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.

It isn’t a trip to Chicago without tasting deep-dish pizza—and this private tour for food lovers will introduce you to true Chicago-style pizza, plus other Windy City specialties. Meet your guide downtown, and be sure to come hungry: You’ll eat hot dogs, Italian beef sandwiches, pizza, donuts, and more. Along the way, see highlights like the Wrigley Building and Magnificent Mile, and learn more about the city’s history and culture.

Discover the heart of Chicago’s architectural legacy on this guided walking tour through the historic Loop District. Step back in time as you explore some of the world’s first skyscrapers and venture inside a collection of the city’s most influential and iconic buildings. Your expert local guide will share captivating stories about the rise of Chicago, the Great Fire, and the visionary architects whose bold designs shaped the skyline we know today. This tour offers the perfect mix of history, design, and city energy—a must for architecture lovers and curious travelers alike. - Explore the birthplace of the modern skyscraper - Step inside landmark buildings like The Rookery and the Palmer House - Learn about the Great Chicago Fire and its lasting impact on the city - Enjoy a relaxed pace through Chicago’s vibrant downtown Loop

Step into Chicago’s past and explore the story of America’s first model industrial town on this guided walking tour through the Pullman Historic District. Once the heart of George Pullman’s luxury railcar empire, this neighborhood is now a National Monument that beautifully preserves its 19th-century charm and revolutionary history. Wander past rows of red-brick homes, elegant civic buildings, and historic landmarks as your local guide shares the fascinating rise and fall of the Pullman Company—and how a workers’ strike here forever changed labor rights across the country. - Explore a National Monument – Walk through one of the best-preserved 19th-century industrial communities in the United States. - Visit historic landmarks – See the Pullman Administration Building, Hotel Florence, Greenstone Church, and the Pullman Historic Foundation Visitor Center. - Discover labor movement history – Learn how the famous 1894 Pullman Strike shaped the future of workers’ rights in America.

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.

Discover authentic Italian cooking in Chicago during this pasta-making class hosted through Cozymeal. Limited to just 8 guests, this immersive workshop showcases the art of crafting fresh pasta dough and creating a full three-course menu. The menu you will prepare includes: - Starter: Bruschetta with ripe tomatoes and basil on crisp bread - Main course: Handcrafted gnocchi with tomato-basil sauce - Dessert: Classic tiramisù with mascarpone and espresso-soaked ladyfingers With personalized instruction from your pasta chef, this small-group class combines hands-on practice with flavorful dining. Guests are welcome to bring wine or beer to enjoy with their freshly made meal.

Chicago is renowned for its dynamic dining scene—and this private walking tour offers a personalized introduction to its must-eats. Pick a time that works best for you, and head to Gino’s East: one of the city’s classic deep-dish pizzerias. From there, set off on a tour of the Loop, where you’ll taste sweet and savory treats—and learn about the city’s architecture, history, and culture as you go.

See the best of the Windy City, all in just half a day—and learn the stories behind its best-known sights—on this private tour. In the morning, meet your driver at your Downtown hotel, hop aboard your private vehicle, and set off with a tour guide in tow. You can look forward to seeing sights like Grant Park, Navy Pier, and Buckingham Fountain—and stopping for photo opportunities along the way.