Top 10 Airbnb Experiences In Chicago, Illinois - Updated 2021

Airbnb Experiences In Chicago, Illinois, USA

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!

1. Chicago bike adventures (from USD 90.0)

Tourists on Bikes
Source: Photo by user Phil Roeder used under CC BY 2.0

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

Duration: 4 hours

130 reviews

2. Hidden thrift shop tour (from USD 20.0)

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.

Shop Hidden Thrift Stores

Duration: 4 hours

190 reviews

3. Glassblowing in an artist studio (from USD 58.0)

Glass Blowing (5075745092)
Source: Photo by user Tulane Public Rel... used under CC BY 2.0

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.

Glassblowing in an artist studio

Duration: 2 hours

346 reviews

4. Chicago food tour (from USD 75.0)

Café by the river - Chicago (3850294479)
Source: Photo by user Serge Melki used under CC BY 2.0

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: Saigon to Stockholm

Duration: 3 hours

193 reviews

5. Sail Chicago's lakefront (from USD 150.0)

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.

Sail Chicago's Lakefront on a Yacht

Duration: 2 hours

197 reviews

6. Jam with a professional musician (from USD 85.0)

Person playing guitar
Source: Pexels

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

Duration: 1 hour

31 reviews

7. Interior architecture exploration (from USD 30.0)

Chicago Architecture
Source: Photo by user Teo Romera used under CC BY-SA 2.0

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.

Explore Dazzling Architecture Interiors

Duration: 2 hours

638 reviews

8. Ring making at a metalsmith's studio (from USD 68.0)

Ring making tools
Source: Photo by Wikimedia Commons user Mauro Cateb used under CC BY-SA 3.0

Photo is only for illustrative purposes

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.

Forge A Ring At A Metalsmith's Studio

Duration: 3.0 hours

9. Lincoln Park Nature Walk (from USD 20.0)

Nature Boardwalk Lincoln Park
Source: Photo by user Alanscottwalker used under CC BY-SA 3.0

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

Duration: 2 hours

12 reviews

10. Craft distillery tour and tasting (from USD 11.0)

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

Duration: 1 hour

141 reviews

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.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

Get Trip101 in your inbox

Unsubscribe in one click. See our privacy policy for more information on how we use your data

Hannah is a freelance writer, list making aficionado, and world traveler currently based in Germany. She is an avid explorer, and believes in creating new experiences to put on her bucket list to...Read more

 Want to contribute as a Local Expert?
Explore Chicago
Good things are meant to be shared!