Top Chicago Seasonal & Special Occasions

Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided brewery tour. Visit unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy plenty of beer samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.

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!

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.

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 Navy Pier, 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 3 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. Also enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers. Attractions may be required to verify proof of full COVID-19 vaccination (14 days past final vaccine dose) before allowing entry. Please review attraction requirements before visiting Chicago.

Tower above the Windy City’s world-famous skyline with admission to 360 Chicago (John Hancock Observatory). Ascend 94 stories to the observation deck of one of the tallest buildings in North America aboard its lightning-fast elevator. Then check out bird’s-eye views of landmarks like the famous Willis (Sears) Tower and the lakefront shoreline, and enjoy a variety of educational exhibits on site. Upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. With mobile tickets, simply scan your phone for direct entry into 360 Chicago.

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 this guided, 2.5-hour, 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 Michigan Avenue. 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.

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 deep into the world of natural history with this Field Museum admission ticket in Chicago. 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. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the 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 at your own pace, the Chicago Explorer Pass by Go City saves you up to 40 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 SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center.

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.

Our flagship vessel boasts a Tiki Chic vibe, two climate controlled decks, two bars, two bathrooms, premium sound system, outdoor and indoor viewing areas. Our upscale "Admirals Lounge" 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.

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.

We'll explore six (6) 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.

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.

Pedal through Chicago’s scary heritage with a 3-hour Halloween bike tour that includes hauntings, tragedies and overflowing cemeteries. Experience the creepiest parts of the city as you follow your professional actor guides through the Halloween streets, and watch them bring Chicago’s ghosts to life. Learn about the infamous ‘Resurrection Mary,’ figure out why the Levee District is so famously haunted, and hear the story of H.H. Holmes, Chicago’s most notorious serial killer.

Experience Chicago's Magnificent Fireworks from the Water with Navy Seal Adventure Boat Are you ready for an unforgettable evening of breathtaking views and heart-pounding excitement? Look no further than our Navy Seal Adventure Boat, where we bring you front-row seats to the most spectacular firework show in Chicago! Get ready to embark on a journey like no other, as we take you on an adrenaline-fueled adventure that will leave you in awe. The Ultimate Waterfront Spectacle Situated on the glistening waters of Lake Michigan, our Navy Seal Adventure Boat offers an unparalleled vantage point to witness the city's iconic firework extravaganza. As the sun dips below the horizon, the anticipation builds, and our expert crew navigates the boat to prime position for the best views of the show. Feel the thrill as the sky comes alive with a mesmerizing kaleidoscope of colors, perfectly synchronized to an enchanting symphony of music.

Enjoy a one-of-a-kind night at the theatre when you attend Chicago’s irreverent and comedic “Drunk Shakespeare” performance. Pick between two different start times, and choose a seating area that suits your budget and preferences. Then, sit back, relax, and prepare to laugh as an actor downs five shots of whiskey before attempting to perform in one of Shakespeare’s plays.

All Day! Sundays are Fun-Days aboard the floating tiki bar. See the Chicago River the Island Party way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax an enjoy a beverage. Have questions about buildings? Our helpful staff will be happy to answer questions.