Top Chicago Spring Break in 2026

Get ready to unleash your creativity at the BYOB Candle-Making Class at Chicago Candle Co. This hands-on workshop invites you to craft stunning, personalized candles from upcycled wine bottles, all while enjoying your favorite drinks. Under the guidance of friendly instructors, you’ll learn the art of glass cutting and soy wax pouring, choosing from a variety of cocktail-inspired scents. Bond with friends or make new ones in a welcoming atmosphere as you create unique pieces that reflect your individual style and eco-friendly values. Perfect for a fun night out or a memorable group activity in the heart of Chicago.

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

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.

Immerse yourself in one of Chicago's most vibrant neighborhoods—and head off the tourist trail to discover sights and bites many visitors miss—on this small-group Chinatown food and walking tour. With your guide in the lead, learn about the cuisine of different regions of China, and discover the history of Chicago's Chinatown. Along the way, enjoy a generous array of tastings, from dim sum to Sichuan cuisine and beyond.

See Chicago your way with flexible hop-on hop-off tickets designed to suit every sightseeing style. Explore the Windy City at your own pace, hopping off to visit top attractions such as Millennium Park, Navy Pier, the Magnificent Mile, and the Chicago Riverwalk while enjoying onboard commentary that adds context to what you see. Perfect for first-time visitors or those short on time, this tour offers flexibility and ensures you don’t miss any of Chicago’s highlights. You can also upgrade your experience to enjoy extra sightseeing time and a panoramic sunset tour for unforgettable skyline views.

Discover a dark, spooky side of Chicago that most tours miss on this adults-only ghost walking tour. Keep an eye out for sinister specters and ghastly ghouls as you explore abandoned buildings and shadowy alleyways near some of Chicago’s most popular landmarks, including the Chicago Theatre, Millennium Park, and the Art Institute of Chicago.

Enjoy a food-focused cruise along the Chicago River and Lake Michigan, departing conveniently from Michigan Avenue. This experience combines city views with curated wine and cheese pairings in a relaxed, social setting. Choose between indoor and outdoor seating for comfort in a range of weather conditions, while the absence of narration allows for uninterrupted conversation. A full-service bar is also available for additional drinks throughout the cruise.

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.

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; which used to be the meatpacking district, now becoming the Chicago Brewery District. Here you'll experience the fabulous, intricate world of the art of beer creation. We will all meet at the first one, introduce ourselves and try some delicious appetizers; where Carla will make a special Homemade Guacamole and Homemade Tortilla chips, and here, the first 3 handcrafted beers (3-5oz beers) are on us. Then we'll walk to the other breweries where you'll have a chance to order other beers and serve your own. Here you can stay as long as you want after the tour. During our expedition, we can all share our opinion about the flavors, the creation, etc... All the breweries are within walking distance.

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

"Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!"

Chicago is well known for its architecture and many visitors admire the buildings on a cruise along the Chicago River. Take your river cruise to the next level aboard a floating tiki bar that allows you to take in all the sights with a drink in hand. Your captain also enhances the atmosphere with island tunes as you enjoy your leisurely sail.

Admire up-close views of the Chicago skyline—and a fireworks show over the city—on this tiki bar boat tour. In the evening, make your own way to the departure point at the Chicago Riverwalk, hop aboard, and get comfortable in the air-conditioned seating area or on the deck. Purchase cocktails and food from the on-site tiki bar, watch the city float by, and then sit back and take in the show.

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding a bike. Dive into the atmosphere of the city’s movement and combine it with tasting the most delicious and iconic treats of the Chi after whetting your appetite, absorbing the unique beauty of the city. Discover more sights in a shorter time using a bike Get a true taste of the City by the Lake following the tips of a local guide Discover iconic neighborhoods and be entertained with historical insights. Learn about the peculiarities of local cuisine and its origins.

Set sail for an unforgettable evening aboard the River Star or Island Time, where the drinks are flowing and the views are unmatched. Enjoy a refreshing beverage as you cruise along the Chicago River and take in breathtaking views of the city's iconic skyscrapers.

Milwaukee offers a wide range of sightseeing highlights and cultural attractions—but it can be challenging to find your own way there from Chicago. Instead, leave the logistics and transit to someone else, and enjoy a hassle-free way to explore, on this small-group day trip. Opt for a cost-effective tour-only option to visit key city sights, or upgrade to add admission to the Harley-Davidson Museum and Miller Brewery or Pabst Mansion.