Top Chicago Self-guided Tours

Tower above the Windy City’s world-famous skyline with pre-booked admission to 360 Chicago—a great way to avoid long ticket lines. 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.

The Best Way to Discover Chicago: Scavenger Hunt & Self-Guided Tour. Play, learn, and walk! Explore at your own pace with a 100% self-guided activity. Start anytime (24/7) with no guides or schedules. Pause for a photo at Maggie Daley Park or a visit to the Shedd Aquarium and resume whenever you're ready—even the next day. This unique team-building activity is perfect for couples, families, and groups. The "Complete City" Package - Everything you need in one app: Interactive Game: Solve puzzles and discover 10+ major attractions, plus hidden gems revealed along the way. Audio & Text: Listen to our audio guide or read the history/legends of each site. Insider Tips: Access hand-picked local restaurant and shop recommendations. What you will visit: Navy Pier, Franklin Delano Roosevelt Bridge, Maggie Daley Park, Millennium Park, The Art Institute of Chicago, Clarence F. Buckingham Memorial Fountain, Queen’s Landing, Field Museum, Shedd Aquarium, and Adler Planetarium.

Take your shot at completing this Chicago Scavenger Hunt around the Loop and River North neighborhoods including the Riverwalk. Complete this solo or build a ScavSquad of up to 5 people and discover the city like never before! Use clues and hints within the app to complete the objectives (if you get stuck, you can skip and go back later). Some objectives have prizes so do your best to complete as many objectives correctly. Once complete, you can view the Leaderboard to see how you did against others.

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

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.

Enjoy a unique creative outlet—and learn the ins and outs of graffiti and street art—during this hands-on urban art workshop. Learn different styles and techniques from your instructors (including guest artists), try out stenciling and spray-painting, and create your own work of art on canvas to bring home at the end of class.

This self-guided walking tour is perfect for last-minute travelers who love chocolate! Travelers will use the eATLAS app for directions on where to go, and what to do--map included. You can start and pause the Adventure whenever it is convenient for you. Chicago was once the “Candy Capital of the World,” and chocolate has been a rich, decadent part of the city’s culinary history longer than deep-dish pizza and Italian beef. Milton Hershey even learned how to make chocolate in Chicago at the 1893 World’s Fair. Some of the world’s most beloved chocolate treats, including Tootsie Rolls, Baby Ruth, Butterfinger, Snickers, 3 Musketeers and Milky Way, were invented or are manufactured here. There are 8 delicious Loop and River North stops on our tour/scavenger hunt. Simply read the clues and follow the directions to guess the answers. Hints are provided if you need help. You won’t be required to buy anything, but if you need a quick pick-me-up, what’s better than chocolate?

Experience Chicago in a new way on this small-group Segway tour. Visit Chicago’s "front yard," and see more of the sights in less time. Glide along the fragrant floral paths of Grant Park to the famous Buckingham Fountain. Then, travel along the banks of Lake Michigan to the Museum Campus for top-notch views of the city’s iconic skyline. Guided Segway training and helmets are included, making this a beginner-friendly tour.

Discover Chicago in a fun new way—and combine your sightseeing with a lively scavenger hunt—on this two-in-one excursion. With your smartphone in hand, set off at a time that works best for you on this self-led tour. Prompted by the game, explore the Windy City's vibrant Loop neighborhood. You'll spot historic buildings, famous streets, and other local landmarks along the way, all while your party solves clues and challenges.

Immerse yourself in Chicago's thriving craft beer scene—and visit locals-loved breweries you'd be unlikely to stumble across otherwise—on this half-day brewery tour. Travel in style, and get in the spirit, aboard a traditional Prohibition–style barrel bus. Visit several unique breweries, and go on behind-the-scenes production facility tours. Discover the science behind the brewing process, and enjoy plenty of beer samples throughout the tour.

Discover Chicago's many delights from the comfort of two wheels. Simply pick up your full-day bike rental with lock, map and helmet and start exploring, either solo or with friends. Make your way through Millennium Park and to historic Wrigley Field, stop for a visit at Navy Pier or spend a couple hours watching sea turtles, penguins and even a piranha at Shedd Aquarium. You get to tour Chicago independently at your own pace and leisure without having to deal with parking or public transit.

Escape the bustle of the city during this one or two-hour kayak rental along Lake Michigan in downtown Chicago. Experience the serene waters of the iconic lake as you paddle at your own pace in a single or tandem kayak, enjoying views of Chicago’s famous skyline. Take breaks along nearby urban beachfronts, with the option to extend your rental time. Stand-up paddleboards are also available for rental.

An immersive clue-solving adventure around the trendy arts neighborhood Fulton Market. Search for real-world clues, solve puzzles, and discover the neighborhood with an experience you'll never forget! Reschedule anytime with no fees. It's a scavenger hunt, escape room, and urban crawl all-in-one. Follow the storyline around town as you find clues and use them to crack codes. Then enter solutions on the app to find out where to go next. Clues can be anywhere - murals, statues, landmarks, and more! Plan on about two hours of playtime, depending on your experience level and how much time you spend exploring along the way. Difficulty level is adjustable - take as many or as few hints as you’d like! Bookings made a week or more in advance receive their kit in the mail. Bookings made less than a week in advance will pick up their kit at the start point on the day of the adventure - exact pickup location is sent after booking.

S. Silvera Charters offers a unique luxury yacht rental for those looking to create unforgettable memories on the water. Perfect for special events or leisurely cruising, this charter allows you to set your own schedule and enjoy a personalized experience. With a minimum rental of three hours, you can relax on board while exploring beautiful coastal views. Captain's fees are separate, ensuring a tailored experience for your group. - Exclusive yacht rental for luxury experiences - Flexible scheduling with afternoon and evening options - Minimum three-hour rental for ample exploration - Personalized service with optional captain at an additional fee

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.

See Chicago your way—and enjoy an active way to explore—with this private, half-day bike rental. Make your own way to the rental facility, choose from a range of bike types (from e-bikes and child bikes to premium road bikes), and set off at your own pace. Accompanied by a map and helmet, you can cycle along the water, explore Millennium Park and the Museum Campus, tour Chicago neighborhoods, and more.

One of the easiest and most affordable ways to explore Chicago's top attractions is through a Chicago Explorer Pass by Go City. Save money compared to buying individual attraction tickets, and create your own sightseeing itinerary by choosing from among more than 35 top sites, including the Skydeck Chicago, a sightseeing cruise, a hop-on hop-off Big Bus tour, Navy Pier, and more.

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.

Experience the adrenaline rush of skydiving without jumping out of a plane at iFly Chicago-Rosemont. With start times available throughout the day, you can easily find a session that fits your busy schedule. Feel confident after a small-group training session, then head into the tunnel for your solo floats. An instructor is present for both 60-second sessions to give you personalized instruction. Afterwards, take home a flight certificate to commemorate your adventure.

The streets of Chicago hold clues to a chilling murder. Can you piece together what happened on this self-guided walking quest? Your smartphone delivers clues, witness statements, and puzzles as you navigate between real-world locations that become your crime scene. Each stop reveals new evidence and suspects. Follow the trail from location to location, piecing together the story while exploring Chicago's streets. The app guides you step by step with an immersive narrative full of twists. This 1–2 hour private detective adventure runs 24/7 — start whenever you want, pause for coffee or photos, and play at your own pace. Available in 5+ languages.

Dive into Chicago’s Magnificent Mile on an interactive scavenger hunt, perfect for families, friends, or team building! Guided by clues on your phone, you’ll solve puzzles, unlock local legends, and discover iconic sites like the Old Water Tower, Tribune Tower, and bustling Riverwalk—plus hidden gems along the way. Go at your own pace, compete for fun, and see the best of Chicago’s lively downtown in a whole new way. Teams of up to six welcome; no local knowledge required—just curiosity and comfy shoes.

Don’t just explore Chicago’s best-known landmarks—put your problem-solving skills and competitive side to the test with this private scavenger hunt experience. The game will be conducted via your smartphone, with a live, remote guide to accompany and assist you. As you go, hunt for clues, discover unusual sights, take part in bonus challenges—and see where you team falls on the national leaderboard.

Discover Chicago's vibrant history through an engaging scavenger hunt in Millennium Park. This interactive experience melds fun and learning as you uncover stories from the city’s founding in 1837 to its iconic landmarks. Explore notable sites like Cloud Gate and the Art Institute, while tackling quizzes that challenge your knowledge. The app-led format allows you to navigate at your own pace, making it perfect for families, friends, or dates. Capture memorable moments as you embark on this unique journey through the Windy City.