Top Chicago Likely To Sell Out in 2026

Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and glide along the Chicago lakefront to view attractions such as Museum Campus, Shedd Aquarium, The Field Museum, and Soldier Field, homefield for the Chicago Bears.

Take in the Chicago skyline from a vantage point most travelers miss on this brunch cruise. Gaze up at the Willis Tower, the Old Chicago Post Office, the Tribune Tower, and much more as you drift along the Chicago River while listening to light commentary and enjoying a curated menu of brunch favorites.

Chicago is famous for its architecture, and the best way to see it is on a cruise down the Chicago River. Glide by historic and modern marvels like the Civic Opera House, Wrigley Building, and Willis Tower from the comfort of an open-deck boat. Live narration reveals each building’s fascinating history, so you'll learn more than you would just observing on your own.

Sample some of the Windy City's tastiest donuts—and head to locals-loved dessert destinations that most visitors miss—on this one-of-a-kind walking tour. With your guide in the lead, head to a number of Chicago’s tastiest donut bakeries, all while exploring the city's vibrant downtown Loop neighborhood. All tastings are included in the tour cost, and vegan, gluten-, and nut-free options are also available upon request.

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Explore Chicago's buzzing food scene—and see some of its best-known landmarks on the way—on this two-in-one walking tour. The small group size offers are more intimate experience as you stroll around the vibrant Loop area, spotting highlights from the Willis Tower to the Rookery building. Indulge in a variety of famous Chicago foods, from deep-dish pizza to the world-famous dipped Italian beef sandwiches.

Immerse yourself in the vibrant flavors of Mexico with a hands-on Tamale cooking class at Su Casa Mexican Restaurant. Guided by experienced chefs, participants will learn the art of crafting authentic Tamales from scratch. This class is tailored for all skill levels, making it an ideal setting for food enthusiasts eager to enhance their culinary repertoire. As you fill your husk with the masa and your choice of filling, anticipate the rewarding moment of tasting your delicious handiwork, complemented by chips and salsa, tacos and a refreshing drink.

Enjoy a quintessential Chicago experience—and see more of the city's highlights in less time—on an architecture-themed boat tour of the Chicago River. Pick from multiple convenient start times, and board your vessel directly from the Chicago Riverwalk. Thanks to your trained docent guide, receive a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

Most Chicago sightseeing tours focus on the city’s key landmarks. But on this unique excursion, you cam dig deeper than surface level, and discover some of the city’s spookiest stories. Pick between private or shared options, and set off to explore the South Loop with your guide. Along the way, see where notorious gangsters like Al Capone operated, hear about their bloody backstories, and even visit several of the state’s most haunted addresses.

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

One of the “original six”, dating way back to 1926, the Chicago Blackhawks are the epitomise NHL history. For an experience filled with tradition and history, look no further than attending a Blackhawks game at the iconic United Center. The Blackhawks are going through somewhat of a transition phase, led by superstar youngster Connor Beard, winner of the 2024 Calder Memorial trophy for the best NHL rookie. The team are looking to return to previous heights that have seen the franchise win 6 Stanley Cup titles. With a capacity of over 23,000, the United Center is designed for maximum fan engagement, featuring excellent sightlines and modern amenities. The giant LED scoreboard ensures that you won't miss a moment of the action, while the state-of-the-art sound system amplifies the crowd's excitement, making every goal feel monumental! Don't miss out on this opportunity of a lifetime to experience the NHL live in a venue that has become synonymous with Chicago’s vibrant sports culture!

Kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks on this scenic lunch cruise along Lake Michigan. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.

Discover Chicago's world-renowned architecture during this sightseeing cruise. Board a comfortable riverboat for a trip down the Chicago River, viewing landmarks like the Willis Tower and the Tribune Tower while listening to in-depth commentary from your guide. Then board a speedboat for an exciting ride up the shore of Lake Michigan for views of Grant Park, the Museum Campus, and other top sights.

Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.

Our "Fluid Art" experience is truly unique. It offers a mesmerizing journey into the world of art unlike any other. Participants are guided through an exciting process using acrylic paints, silicone, a hair dryer, and a gas burner to create captivating patterns on canvas. This dynamic and spontaneous art form is suitable for everyone, whether you're an art enthusiast or a beginner. You'll be amazed by the intricate and unexpected designs that emerge, making each piece one-of-a-kind. It's a therapeutic and enjoyable activity that guarantees a memorable artistic adventure.

Enjoy waterfront views of downtown Chicago on a 2-hour brunch cruise through the heart of the city. Board a luxurious yacht at Navy Pier then relax on deck with a complementary mimosa. Find a comfortable spot on the three climate-controlled observation decks, and enjoy a sumptuous buffet while the onboard DJ spins a leisurely afternoon playlist. Capture unforgettable images of downtown skyscrapers and architectural landmarks as you navigate along the historic shoreline, then loop back and finish your outing at the bustling Navy Pier.

Enjoy a memorable Chicago experience on this haunted pub tour. Your costumed guide, dressed as a Flapper or 1920s Gangster, will lead you on a mile-long journey while telling spooky stories of forgotten cemeteries, lingering spirits, and more. Stop at three different bars for drinks (at own expense) as you learn the secret tales behind Chicago’s haunted past.

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.

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.

Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is as scenic as it is delicious! You'll savor a chef-prepared buffet and bottomless mimosas while in our comfortable indoor areas. Marvel at unparalleled views of Chicago’s iconic landmarks, such as Willis Tower and Navy Pier from inside or enjoy fresh breezes on the open-air decks. This fun-filled brunch cruise experience for all ages is complete with lively DJ entertainment, dancing, games, and a fully stocked cash bar. Elevate your weekend plans with a one-of-a-kind brunch cruise on the water!

In the heart of Chicago, near Wrigley Field, a culinary adventure awaits. Led by Rakhi, a professionally trained chef and Le Cordon Bleu graduate with experience working with Bobby Flay, this private cooking class immerses you in the rich flavors of Italian-American cuisine. Over 2.5 hours, you'll learn to prepare iconic dishes such as Chicken Vesuvio, hot fried chicken, and homemade desserts, all while enjoying a relaxed and interactive atmosphere. With the chance to tailor your menu, every class becomes a unique experience that celebrates Chicago's vibrant food culture. Gather your friends or family for a memorable evening of cooking and dining together.