Top 10 Likely to Sell Out in Chicago

Destination: Chicago.
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.
Known For: Chicago Private Sightseeing Tours, Chicago Likely to Sell Out, Chicago Day Cruises, Chicago Sailing, Chicago Water Tours, Chicago Sightseeing Cruises, Chicago Full-day Tours, Chicago Likely To Sell Out.
Duration: Around 2 hours.

Destination: Chicago.
Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a recent transplant to Chicago or have lived among the Windy City’s ‘others’ for years, you’re about to get a haunted history that may leave you with more memories than you dare to retain.   Tours begin at the haunted Harry Caray’s Italian Steakhouse in downtown Chicago. A costumed guide will lead tour goers on a walking journey exploring the creepy past of one of Chicago’s most famous bootleggers, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home.
Known For: Chicago Private and Luxury, Chicago Historical Tours, Chicago Likely to Sell Out, Chicago Food & Drink, Chicago Small Group, Chicago Walking Tours, Chicago Excellent Quality, Chicago Ghost Tours, Chicago Likely To Sell Out.
Duration: Around 1 hour and a half.

Destination: Chicago.
This is the only tour in Chicago that explores the movie "Ferris Bueller's Day Off" from the perspective of art. It's also the only walking tour that immerses you in the actual artwork featured in the 1986 American teen film. Over the course of the tour, you'll visit 3 floors of the museum, see 16 pieces of art, and leave with an appreciation of the works, their relationship to characters, and their placement in the camera's frame. ⚠️ NOTE: Admission to the Art Institute of Chicago is NOT included in the public walking tour. The tour starts under the stairs in the *Modern Wing* of the Art Institute, Griffin Court. Guests must digitally sign a general waiver of liability. Guardians must sign waivers for children under the age of 18.
Known For: Chicago Likely To Sell Out, Chicago Art Tours, Chicago Private and Luxury, Chicago Walking Tours, Chicago Movie Tours, Chicago Small Group, Chicago Cultural Tours, Chicago Likely to Sell Out, Chicago Seasonal.
Duration: Around 1 hour and a half.

Destination: Chicago.
Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza, Garrett’s Popcorn, and Do-Rite Donuts while exploring top city landmarks such as the Tribune Tower, Wrigley Building, and Buckingham Fountain. Led by a friendly local guide, this experience blends Chicago’s most famous eats, rich culture, and great photo ops — the perfect way to enjoy the best of the Windy City in one delicious day. Tour Ticket Includes: • 1 Portillo’s hot dog • 1 small Garrett’s Popcorn • 6" Al’s Italian Beef Sandwich • 1 slice of authentic Chicago deep dish pizza
Known For: Chicago Food & Drink, Chicago City Tours, Chicago Likely to Sell Out, Chicago Culture, Chicago Likely To Sell Out, Chicago Walking Tours, Chicago Culinary Tours, Chicago Half-day Tours, Chicago Private Sightseeing Tours.
Duration: Around 4 hours.

Destination: Chicago.
With a deep knowledge of Mexican cuisine and a passion for cooking with authentic ingredients, Carla brings the art of Mole-making to your table. Each dish is crafted with care and expertise, resulting in a dining experience that is both flavorful and memorable. Whether you're a fan of Mexican cuisine or simply seeking a new and exciting culinary adventure, Carla's Mole experience is not to be missed. Book your seat at the table today and get ready to savor the authentic taste of Mexico!
Known For: Chicago Restaurants, Chicago Dining Experiences, Chicago Cooking Classes, Chicago Lunch, Chicago Small Group, Chicago Likely To Sell Out, Chicago Food & Drink, Chicago Likely to Sell Out.
Duration: Around 2 hours.

Destination: Chicago.
Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chicago’s Air & Water Show from the Best Seat on the Lake! 10AM SAIL: Our first sail will depart at 10am sharp. Our first event will be the Air and Water Show, and will showcase a wide variety of aircraft, and demonstrations, which will be watched from the *best location, as determined by the Captain. We will return to our dock by 12:30pm. 1PM SAIL: This sail will depart at 1PM sharp. As this is our second sail for the Air and Water Show, this sail will also showcase a wide variety of aircraft, and demonstrations, INCLUDING THE MAIN EVENT. This will be watched from the *best location, as determined by the Captain. We will return to our dock around 3:30pm, but this may be delayed, if the show is delayed, to ensure your viewing of the main event, if it happens.
Known For: Chicago Likely to Sell Out, Chicago Water Tours, Chicago Sailing, Chicago New Product, Chicago Likely To Sell Out.
Duration: Around 2 hours and a half.

Destination: Chicago.
Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a little bit of culture, some amazing architecture, & a ton of great photos then this is the tour for you. The morning will start with meeting with your friendly local guide at the meeting point. From there your tour will begin as you start your day walking throughout Chicago and exploring the most famous locations in the city. This half-day tour will be fully packed with famous landmarks, vintage architecture, secretly located spots and much much more! ==== Full schedule 10:00 AM- Meet your Guide at the Grand Subway Station 10:10 AM- Walk along Magnificent Mile 10:20 AM- Stop at Wrigley Building & admire Tribune Tower 10:50 AM- Explore Pioneer Court 11:20 AM- Explore Millennium Park & see Cloud Gate 11:55 AM- Check out an Iconic fountain 12:20 AM- Chicago Riverwalk 1:00 PM- Explore Navy Pier 2:00 PM- Get dropped off by your guide at Millennium station
Known For: Chicago City Tours, Chicago Likely to Sell Out, Chicago Likely To Sell Out, Chicago Walking Tours, Chicago Half-day Tours, Chicago Private Sightseeing Tours.
Duration: Around 4 hours.

Destination: Chicago.
Experience the perfect pairing of fresh pasta and craft spirits in this hands-on cooking class with a talented chef, hosted at a local distillery in Chicago! Learn the time-honored techniques of pasta-making as you mix, knead, roll, and cut your own pasta from scratch using just eggs, flour, and olive oil. Then, prepare a rich marinara sauce with onions, mushrooms, spinach, and tomatoes, with the option to add beef for a meaty variation. Enjoy the lively atmosphere of the distillery, where you can sip on expertly crafted spirits while perfecting your culinary skills. Whether you’re a pasta lover, a food enthusiast, or just looking for a fun and interactive night out, this class is the perfect way to learn, sip, and savor. Book your spot today for an unforgettable pasta-making experience in the heart of Chicago!
Known For: Chicago Likely To Sell Out, Chicago Cooking Classes, Chicago Likely to Sell Out, Chicago Food & Drink.
Duration: Around 2 hours.

Destination: Chicago.
Join us for the most memorable experience you will have while visiting Chicago! For runners from around the world, this is definitely a “bucket list” activity. This casual paced, guided running tour will take you through and around the most iconic sights that Chicago has to offer. We will take you along the Lake Michigan shoreline where you will take in the most spectacular views of the beautiful city skyline, through Downtown and “the Loop” to cross the Chicago River where we will share some of the incredible history that has made Chicago so famous, from gangsters to marine disasters, and finally up Michigan Avenue to enjoy the cultural and architectural highlights of the Chicago Art Institute, famous historical building and so much more! You will not break any personal best running times, though, as we make stops along the way to talk about the sights and take pictures for you to share with friends and loved ones!
Known For: Chicago Seasonal, Chicago Private and Luxury, Chicago Likely to Sell Out, Chicago Small Group, Chicago Likely To Sell Out, Chicago Running Tours.
Duration: Around 1 hour and a half.

Destination: Chicago.
Each dish is crafted with the freshest ingredients and a focus on traditional cooking techniques, resulting in a dining experience that is both authentic and delicious. Whether you're a foodie looking to expand your palate or simply seeking a unique and memorable night out, Carla's Yucatan dinner is not to be missed. Book your seat at the table today and get ready to embark on a culinary journey you won't forget! Ronaldo and Carla also have a thing for Yucatan inspired cocktails so expect some delicious drinks to accompany all that food!
Known For: Chicago Restaurants, Chicago Dinner, Chicago Food & Drink, Chicago Seasonal, Chicago Dining Experiences, Chicago Likely to Sell Out, Chicago Small Group, Chicago Likely To Sell Out.
Duration: Around 2 hours.