Top Chicago Self-guided Tours & Rentals

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.

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.

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, 2.5-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.

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).

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.

Discover the adrenaline rush of skydiving without setting foot on a plane at iFly Chicago-Rosemont. Offered 9am to 10pm, you can easily find a session that fits with 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.

Explore Chicago's Chinese food scene on this walking tour in the Chinatown district. With a guide, learn about the cuisine of different regions of China and how Chinese culture has influenced Chicago and other areas. Enjoy included tastings from restaurants and other food venues in Chinatown—a great way to start a night out in the city.

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. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two years from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.

Explore Chicago's buzzing food scene with a small group on this small group walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste classic Chicago foods, from deep-dish pizza to dipped Italian beef sandwiches.

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, Skydeck Chicago (Opening with reimagined experience in Spring 2021), and the Field Museum plus your choice of admission to 3 of the following attractions: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Chicago, and the 360 CHICAGO Observation Deck. 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.

Named for the cable car turnarounds and the prominent elevated railway that encircled the area at the end of the 19th century, the Loop is Chicago's commercial and cultural core. On today's epic scavenger hunt of Chicago, you'll uncover the area's best sights and rich history. Along the way, you'll visit Cloud Gate, Art Institute of Chicago, and the Federal Reserve Bank of Chicago. It's time to strap on those walking shoes, round up some friends and book your Chicago Loop scavenger hunt today! What You'll See: Tiffany Dome, The Bean, Crown Fountain, Art Institute of Chicago

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.

Cruise around Lake Michigan and enjoy spectacular views of Chicago on an Aqua Water Trike. This 30-minute rental lets you explore at your own pace and experience the city from the water. There is space for two people per bike and no experience is required—simple hop aboard and pedal your way around the lake.

Alley Kat Adventures is an Austin, TX-based event design company offering city scavenger hunts in 30 cities in the US and Mexico as well as custom events worldwide. Our specially hand-crafted, interactive quests are equal parts tour, cultural experience, creative challenge, detective hunt, & social experiment! Guests get to discover hidden gems off the beaten trail while completing fun missions! Find an obscure repeating theme in various street art around town, marvel at giant digital art curated just for you, hunt down an iconic and locally famous old elevator, and more!

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.

Walk around Chicago while completing the Operation City Quest scavenger hunt! Use an app to find a list of objects around the city in any order you choose and perform fun challenges for points. Collect points and take a look at your score compared to others across the country. All of our scavenger hunts have a remote host via chat to help along the way. Come out and explore with us in Chicago.

Zombie Scavengers takes you on an adventure in Chicago to survive the zombie apocalypse! Use our app and some strategy to find a list of items needed to survive, in any order you'd prefer, around the city. Find the survival items to get points and do fun zombie themed challenges for points as well. Contrive a plan to get your survival team the most points in order to survive the apocalypse! Your remote host will follow along virtually and provide support if you need it. Can you survive the apocalypse in Chicago?

Walk around Chicago while completing the Wacky Walks scavenger hunt. Use an app to find a list of objects around the city and participate in fun challenges for points. Collect points and take a look at your score compared to others around the country! All our Scavenger hunts have a live remote host to help along the way. Come out and explore with us in Chicago.

With Crazy Dash, you'll use an app to explore Chicago in this exciting scavenger hunt! Use an app to find things around the city in any order you want, take photos, and collect points. At the end, take a look at the rankings to see your score compared to others across the country. All scavenger hunts have a live remote host that will help via chat. Crazy Dash is our most easy-going scavenger hunt. Come join us in Chicago today!

Discover Chicago in a fun new way on this 3-hour scavenger hunt. Jump into the middle of an exciting adventure around the Chicago Loop — to the historic buildings, famous streets and plethora of real-life locations around town. Discover both well-known and overlooked sites, solving clues and completing challenges via smartphone while learning the local history of the Windy City. Teams of 2- to 5-people are welcome.

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.

It's an intimate experience for 2 to 6 people. No mass crowds associated with tour boats. They get to enjoy the river with the luxury of having their own private boat with a professional, licensed, captain. Cocktails, and other beverages, are available from the bar for purchase before boarding.

The Chicago 3Quest Challenge is a scavenger hunt done on an app where players will find objects (given in the form of riddles) and complete fun challenges for points. The items & challenges are separated into 3 quests. Complete quest 1, then quest 2, then quest 3 in order to finish the game! Set a time limit for yourself to see if you can do all 3 quests in 2 hours! You'll have a remote host who will chat with you during the game if you need anything! The objective is to see if you can complete all 3 quests! Come play 3Quest Challenge in Chicago today!