With its bold, breathtaking skyline, dizzyingly delicious food scene, and world class attractions, Chicago is a city that constantly dazzles and delights. From touring the impressive architecture to exploring the plethora of exceptional museums, there is plenty to see and do in this brilliant Midwestern metropolis. Visit well-known landmarks like the Cloud Gate and Buckingham Fountain, and take a picture at the iconic red and yellow marquee of Chicago Theater! Enjoy stunning panoramas from the 360 CHICAGO Observation Deck, or embark on a history tour of the city on a Chicago Architecture River Cruise where you’ll learn about renowned buildings like the Willis Tower and the Tribune Tower. Arts aficionados will love checking out the staggering collections in the Art Institute of Chicago, while sports fans won’t want to miss a tour of Wrigley Field, the second-oldest MLB ballpark in the country. No matter where your interests lie, this city is an exciting destination of exceptional attractions. These Airbnb experiences are a great way to see more of the fantastic attractions in Chicago. Read more about them below!
Travel by bicycle to some of the most popular spots across Chicago! On this five-hour, customizable cycling tour, your experienced guide will provide you with a bike and lead you past iconic attractions, and through some of Chicago’s vibrant neighborhoods, including the former “Polish Downtown”, Fulton Market, Chinatown, and Irish Bridgeport. Admire soaring skyscrapers and vivid street murals as you cycle under the historic “L” train, past gangster-related sites from the 1920s, and around Chicago’s dramatic downtown architecture.
Chicago bike adventures
Scout out the best souvenirs and shop at local thrift stores in this 4.5-hour shopping experience tour. Chicago brims with fantastic thrift stores, and your experienced thrifter guide knows all the hidden gems in the city! After a quick coffee and a snack, your guide will take you to three stores and you’ll spend an hour at each scoping out unique finds. Whether you’re scouring the racks for a leather jacket or looking to snag the perfect ornament for your house, this tour may just help you find it.
Hidden thrift shop tour
Take home a unique memento from your trip to Chicago—an original, hand-blown glass ornament that you crafted yourself! This tour of a glassblowing studio will walk you through the process of creating beautiful, one-of-a-kind pieces, and conclude with a hands-on workshop. At the end of the two-hour lesson, you’ll have made a gorgeous paperweight or bowl. Your souvenir has to be picked up two days later, though, as the glass must have a chance to cool fully. You can also arrange for your piece to be shipped to you, if you live in the continental United States.
Chicago brims with gastronomic flair, and you can discover new flavors and favorites in this 3.5-hour tour. There are so many diverse dishes to try on this foodie extravaganza! This tour leads you through two of Chicago’s vibrant neighborhoods, Argyle and Andersonville, and includes 10 different food tastings! As your chef-turned-guide leads you across town, you’ll snack on Vietnamese summer rolls in Chicago’s Southeast Asian community, sip Swedish glögg in a former speakeasy, sample spices from Middle Eastern food traditions, and taste one of the best apple pies in America.
Chicago food tour
One of the best ways to experience Chicago is out on the water. This 2.5-hour cruise takes you along the picturesque Lake Michigan where you can enjoy spectacular panoramas of the city. Escape the hustle and bustle of the downtown as you skim the glassy waves of the lake and glide past landmarks like Navy Pier. In the summer, you might even catch a fireworks display! This laid-back cruise is perfect for taking in the sunshine, the surf, and the skyline.
Sailing Chicago's lakefront
Address: Monroe Harbor, Chicago, IL
The Chicago Distilling Company opened its doors in Logan Square in 2013, and has been serving fantastic craft spirts ever since. On this one-hour tour, you’ll learn the process of how grain makes it into your glass as a top-notch spirit. You’ll also get to sip samples from the products made on-site and enjoy cocktails in the Tasting Room! You must be at least 21 years old to attend the tour.
Craft distillery tour and tasting
Address: 2359 N. Milwaukee Ave Chicago, IL 60647
This unique tour gives you a behind-the-scenes look at an artisan metalsmith’s studio. Over the course of three hours, you’ll learn the basics of the craft, including texturing the metal, using mandrels and hammers to form the metal, soldering, and decorative finishing. By the end of the lesson, you’ll have a stunning handmade ring of your own design and creation! All the tools and metal are provided for you, and you can bring your own alcoholic beverage if you would like to.
Ring making at metalsmith's studio
Whether you’re an expert or a novice musician, this experience is a unique activity to include in your Chicago itinerary. During this hour-long lesson, you’ll get the chance to play and record music with a Chicago musician and producer. This experience gives you a sneak peek into the world of professional musicians, and provides the opportunity to record your performance with professional equipment.
Jam with a professional musician
The Windy City may be home to the world-famous Art Institute of Chicago, but the stunning skyscrapers throughout the downtown are equally remarkable masterpieces! This incredible two-hour tour lets you explore the breathtaking architecture throughout the city and features some of the Chicago’s more overlooked buildings. As you explore both the exterior and interior design of the buildings, your knowledgeable guide will share stories and facts about Chicago’s rich and long architectural heritage.
Interior architecture exploration
This delightful walking tour lets you explore the wonderful attractions and beautiful views within Chicago’s Lincoln Park. Ramble among unique sculptures and peaceful gardens, snack on delicious pastries from a charming cafe, and admire the panoramas of the city. This tour also includes a visit to the Lincoln Park Zoo. This 1.5-2 hour excursion is perfect for a laidback afternoon in the city.
Lincoln Park Nature Walk
The countless charms of Chicago
With some of the country’s best art, entertainment, shopping, and dining experiences, Chicago is a city of unceasing enchantment. There is so much to see and do in this city, from architecture tours to sailing excursions. These Airbnb experiences make unique additions to your trip itinerary! Start planning your trip today, and book a tour with a local guide.
Get Trip101 in your inbox
You can buy and claim online, even after you've left home. Travel insurance from WorldNomads.com is available to people from 140 countries. It’s designed for adventurous travellers with cover for overseas medical, evacuation, baggage and a range of adventure sports and activities.
*5% off when you book with our promo code: TRIP101
*For our Canadian and US travellers, unfortunately due to financial services laws, we cannot provide a discount. This promotional code cannot be used with any other discount offer, including World Nomads Members’ discount for travel insurance policy holders.