Top Chicago Seasonal & Special Occasions

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.

Do you have what it takes to solve puzzles, figure out clues, and flee your escape room—all in just 60 minutes? Find out when you book a Chicago escape room experience. Pick from five themed rooms: The California-themed Gold Rush; Special Ops: Mysterious Market, where you play secret agents; Prison Break, where you escape from a warden; the extraterrestrial-themed Mission: Mars; and the Heist, where you track down an art thief.

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.

Sit back and take in some magic during this outrageous, hilarious show. Show up a few minutes before curtain time to get the best possible general admission seat and start sipping the drinks you brought. Cups and bottle openers are available for your use. Buying your tickets in advance means less waiting for entry; you'll be sure to get the day and time you that fits your schedule.

Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like the Wrigley Building and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).

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 Shedd 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.

Tower above the Windy City’s world-famous skyline with admission to 360 Chicago. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

Experience Chicago like never before on this small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city’s iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.

Experience Chicago like never before on small-group Segway tour. Visit popular Grant Park and see famous Buckingham Fountain, with the Windy City skyline as the backdrop. Glide along the lakefront, taking in views of the Field Museum of Natural History, Shedd Aquarium, Soldier Field, Adler Planetarium and beyond. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toe shoes.

Enjoy a unique creative outlet—and learn the ins and outs of graffiti and street art—during this hands-on urban art workshop. Pick from multiple class times, and make your own way to the Chicago studio. You’ll learn different styles and techniques from your instructors (including guest artists), can try out stenciling and spray-painting, and can even create your own work of art on canvas to bring home at the end of class.

Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see Buckingham Fountain’s breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, then witness Chicago's weekly summer fireworks display at Navy Pier from a secret location. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.

Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Delve into the world of natural history with tickets to the Field Museum in Chicago. Choose general admission, or upgrade to visit one or several special exhibitions. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. You can also take advantage of free daily tours led by Field Museum docents.

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.

The easiest and most affordable way to explore some of Chicago's top attractions, the Chicago Explorer Pass by Go City saves you up to 50 percent off compared to buying individual attraction tickets. Create your own sightseeing itinerary by choosing 2, 3, 4, 5, 6 or 7 attractions, tours, and activities from among more than 25 top sites, including the Skydeck Chicago, a sightseeing cruise, a hop-on hop-off Big Bus tour, Navy Pier, and more.

Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. 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.

The famous Tall Ship Windy sunset sail is truly famous. Used in many world-renown photos, backdrops for special events, weddings, or just an evening out, the sunset sail aboard one of the only four-mast Schooners still in operation will not disappoint. You will enjoy a sail on Lake Michigan and at just the right moment, S/V Windy will gently turn toward the Chicago skyline for a view of our spectacular sunset. Sit back and relax, enjoy some soothing music, and gently complete your day with this dramatic sunset. ** Please note, tickets purchased for sunset sails on Monday evenings will be upgraded from our traditional 75 minute sail to our Monday Night Blues Summer Concert Series, which departs the dock at 7pm and returns at 9pm. Enjoy live Blues music and 45 extra minutes aboard beautiful Tall Ship Windy!

Our flagship vessel boasts a Tiki Chic vibe, two climate controlled decks, two bars, two bathrooms, premium sound system, outdoor and indoor viewing areas. You can upgrade to our upscale "Admirals Lounge"which features top-shelf alcohol, including the captain's private reserve. Your adventure starts on the Chicago Riverwalk when you board vessel. Enjoy a beverage as you complete the unique experience of transiting the Chicago Locks. Once on Lake Michigan take in the stunning views of Chicago's skyline.

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.

Discover many of Chicago’s best-known landmarks—and see the city dressed up in its festive best—on this holiday walking tour of the Windy City. Meet your guide in the afternoon, be sure to come bundled, and set off with a small group. In between admiring sights like Millennium Park, the Chicago Theater, and more, you’ll also visit the city’s Christkindlmarket, see Christmas window displays, and more.

Stroll through Chicago's winter streets, lit up for the holidays, on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk. Seasonal craft beer tastings help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.

This Wine & Cheese 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 tasting wine and cheese pairings. 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.

Most people have to decide between a boozy Sunday and a river cruise. During this special boat ride in Chicago, you get the best of both worlds. Enjoy a range of mimosas and other brunch drinks for purchase as you cruise down the Chicago River. Enjoy front-row seats as you pass by iconic skyscrapers and other downtown landmarks, with staff available to answer your questions.