Airbnb Chicago, Illinois: Studios, Lofts, Apartments, Condos, Penthouses, Brownstones, Guesthouses, Villas, Mansions & Vacation Rentals

Chicago Airbnbs: 12 Stunning Vacation Rentals!

As the third most populous city in the US, it’s no surprise that Chicago attracts more and more visitors each year. The city has so much to offer all types of travelers! There’s a good reason why Chicago has been voted the best large city in the US for four years in a row by Condé Nast Traveler.

If you’re looking for a culture fix, the Windy City is home to some of the best museums in the US including the Art Institute of Chicago. If history is your thing, head over to Old Town and marvel at the spectacular Victorian-era buildings. And if you’re just looking for a carefree vacation, the city boasts excellent boutique shops, lush parks, and endless entertainment options.  

Chicago has also emerged as an excellent city for foodies. No trip to the city is complete without indulging in its famous deep-dish pizza and Chicago-style hot dogs. And if you want to sample the city’s best restaurants – and there are a lot of them – be sure to pay a visit to “Restaurant Row” and Fulton Market.

Whether you’re planning a memorable family holiday, a romantic retreat, or a celebratory trip with friends, there’s no doubt that you will find a unique Airbnb in Chicago perfect for you. From Victorian homes to swanky penthouses and luxurious estates, the options are plentiful. 

Finding the perfect vacation home might seem overwhelming, so we have picked out 12 of the best Airbnbs in Chicago to make your decision just a little bit easier!

Top 10 Things To Do in Chicago

Chicago Airbnb: Studios, Lofts, Apartments, Condos, Penthouses, Brownstones, Guesthouses, Villas, Mansions & Vacation Rentals
  1. Ride the iconic Ferris wheel at the historic Navy Pier. This is by far the most popular thing to do in Chicago!
  2. Enjoy a bird’s-eye view of the city from the 1,030-high observation deck at 360 CHICAGO (formerly known as the John Hancock Center).
  3. Go running, walking, or cycling along the 2.7-mile Bloomingdale Trail (also known as the 606). 
  4. Eat your way through Restaurant Row. Located on Randolph Street in West Loop, this area is home to Chicago’s best restaurants.
  5. Peruse over 300,000 works of art at the iconic Art Institute of Chicago
  6. Explore the hip boutiques, diverse restaurants, and historic buildings in Logan Square.
  7. Take a stroll along the 18-mile Lakefront Trail where you’ll come across beautiful beaches and massive parks.
  8. Snap a selfie at the Cloud Gate (locally known as “the Bean”) at Millennium Park. 
  9. Catch a Cubs game at the historic Wrigley Field. The baseball stadium was built in 1914!
  10. Go bar hopping along Milwaukee Avenue and Logan Square. Be sure to hit up the local favorite Revolution Brewing.
  11. Take a road trip to nearby Rockford or Milwaukee – a couple of the best day trips from Chicago.

Why Stay in an Airbnb in Chicago

Why Stay in an Airbnb in Chicago, Illinois

There are dozens of cool boutique hotels in Chicago, but staying in an Airbnb comes with lots of perks. First off, you’ll have the chance to stay in a local neighborhood. Also, Chicago is a massive city, so it’s helpful to get travel and dining tips from your friendly Airbnb host.  

The selection of unique Airbnbs in Chicago is extensive. You can opt for modern homes with stunning city views, historic homes in high-end neighborhoods, or luxurious villas in the heart of town.

By choosing to stay in an Airbnb in Chicago, you’ll generally more value compared to a hotel. Most Chicago vacation homes are much nicer and more spacious than your average hotel room. Plus you’ll have a kitchen to prepare home-cooked meals, which saves on dining costs. Although we definitely recommend sampling as many of Chicago’s famous restaurants as possible!

And if you are traveling as a large group, Airbnbs often cost less per person than paying for multiple hotel rooms. This is especially true in the summer months, on holidays, and during annual festivals when tourism is at its height.  

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The 12 Best Airbnbs in Chicago, Illinois

Best Chicago Airbnbs for Couples and Solo Travelers

1. Stylish Studio in the Heart of Logan Square

Best Airbnbs in Chicago, Illinois: Logan Square Modern Studio
Images courtesy of Airbnb

This beautiful studio apartment is located right in the heart of the hip Logan Square neighborhood. With a bedroom nook and tons of extra sleeping space, this cozy Chicago Airbnb can sleep up to six guests. It’s perfect for couples wanting a romantic getaway or small families looking to be right in the heart of the action! 

The thoughtful owners have put love and care into every detail of this Airbnb. You’ll find cool amenities all around the studio including a record player with a selection of vinyl, original artwork, and tons of plants.  The hardwood floors, picture-perfect vaulted ceilings, and modern décor all work to give this vacation home its unique character. 

You can have a movie night in the homey living room, catch up on some reading on the comfy futon, or get some work done at the designated workspace. The kitchen is surprisingly spacious and has everything you need to cook at home. Enjoy your meals and morning coffee in the sun-drenched breakfast nook.

If you feel like going out, all of Logan Square’s best restaurants, shops, and cafes are a short stroll away. Be sure to brunch at local favorite Lula Café and grab a beer at the ultra-popular Revolution Brewing!

2. Modern Studio with Private Yard and Hot Tub

Best Chicago Airbnbs and Vacation Rentals: Modern Studio with Hot Tub
Images courtesy of Airbnb

This unique Chicago Airbnb is tucked away in a quiet residential neighborhood near Logan Square. With modern furniture and quirky decor, this hip studio is the perfect mix of comfort and cool. It’s a great option for couples or business travelers looking for a convenient home base during their trip to the Windy City. 

Expect to find funky features throughout this vacation rental – from cow print furniture to an intricately carved bathroom door. You can relax in the padded butterfly chairs, lounge around on the plush sofa, and get a good night’s sleep on the king-sized bed. The kitchenette is compact but fully outfitted in case you want to prepare meals during your stay.

One of the most unique things about this studio is that you’ll have access to a private fenced yard. Be sure to take advantage of the hot tub after a day exploring Chicago! And if you want to get outside for a walk, Humboldt Park is right next door. 

3. 1-Bedroom Suite in Historical Edgewater Glen Home

Best Airbnbs in Chicago, Illinois: Historic Edgewater Glen Suite
Images courtesy of Airbnb

With its homey decor and stylish accents, you’ll feel right at home in this colorful 1-bedroom suite. This Chicago Airbnb is located on the first level of a historic home in the lovely and historic Edgewater Glen neighborhood. 

Step inside and you’ll find a beautiful living space full of modern decor. The living room boasts a tufted sofa, a large flat-screen, and massive picture windows that let in plenty of natural light. The brick masonry wall and rustic wood trimmings add to the historic and charming ambiance of this one-of-a-kind Airbnb. 

The kitchen features high-end stainless steel appliances, marble countertops, and a breakfast bar. The space is equipped with everything you need to make a romantic dinner for two! Head out to the quaint porch, where you can enjoy your morning coffee.  

This Airbnb is conveniently located near public transportation and within walking distance of some of Chicago’s best attractions. You’re just minutes from the restaurants and historical sights on Clark Street. Plus, Loyola University and two lakeside beaches are just blocks away!

4. Division Street Designer Home in Wicker Park

Best Chicago Airbnbs and Vacation Rentals: Division Street Wicker Park Designer Home
Images courtesy of Airbnb

If you’re looking to be right in the heart of the action, this is one of the best Airbnbs in Chicago! This 1-bedroom designer home is nestled right in the middle of Wicker Park and right next to all the bars, restaurants, and cafes on Milwaukee Avenue and Division Street. 

The thoughtful owners have gone the extra mile to ensure that guests have a comfortable stay. With vaulted ceilings, natural wood floors, and a 150-year-old antique gold floor mirror, the living area is just picture-perfect. You can kick back and relax on the leather sofa and watch TV on the large flat-screen.

If you like to cook, you’ll absolutely love the chef’s kitchen, which features top-of-the-line appliances, black granite countertops, and a marble backsplash. You’ll find everything you need to whip up gourmet meals at home. The owners have even installed a reverse osmosis filtered drinking water system in the kitchen so there’s no need to buy bottled water!

Head into the separate bedroom and you’ll find a canopy bed with a Tempur-Pedic memory foam mattress, a floor-to-ceiling library, and a desk in case you need to get some work done. 

Best Chicago Airbnbs for Small Groups and Families

5. Chic 2-Bedroom Apartment in Historic Victorian Home

Best Airbnbs in Chicago, Illinois: Historic Victorian Apartment
Images courtesy of Airbnb

Located on the third story of a Victorian home in downtown Oak Park, this chic 2-bedroom apartment might just be the most adorable Airbnb in Chicago! With funky vaulted ceilings, wooden beams, and exposed brick, this vacation rental just oozes charm. 

The living room is chock full of thoughtful touches – from the classy chandelier to the comfy couch and the artsy sculptures. There is also a smart TV that’s perfect for unwinding with a relaxing movie night. 

The light-filled kitchen has sleek black appliances and everything you need to prepare gourmet meals at home. You can eat at the 4-person dining table in the living room or head out to the shared patio for alfresco meals. 

The main bedroom boasts a comfy queen-sized bed with luxury linens. You’ll love the eccentric artwork, the stylish basket pendant light, and cathedral ceilings. The second bedroom is located in the turret of the property so it’s actually round! 

6. Emil Bach House: Perfectly Restored Frank Lloyd Wright House

Unique Chicago Airbnbs and Vacation Rentals: Prairie-Style Home Designed by Frank Lloyd Wright
Images courtesy of Emil Bach House

If you’re an architecture buff, then don’t miss out on the chance to stay in a home designed by legendary architect Frank Lloyd Wright! The Emil Bach House was built in 1915 but has been carefully updated with modern amenities while keeping its historical elements and original design intact. 

This 2-bedroom Prairie-style home can sleep up to six. And the study has a sofa bed and can be used as a third bedroom if you need more space. 

With stone and wood trimmings, an inglenook fireplace, and a long wood dining table, the living room is a work of art. The spectacular table was designed by Wright to break up the living room and kitchen. It’s perfect for celebratory meals!

You’ll love all of the unique features this Airbnb has to offer. You sip a glass of wine in the Japanese tea room, enjoy the breeze from nearby Lake Michigan on the screened-in porch, or prepare gourmet meals in the modern kitchen.

Head upstairs and you’ll find an open-air deck with plenty of patio furniture. If you need more space, gather in the large, carefully manicured backyard!

Check Price & Availability on tripadvisor

7. Stunning Condo in Fulton Market

Coolest Airbnbs in Chicago, Illinois: Condo Near Fulton Market
Images courtesy of Airbnb

This stunning 3-bedroom condo is the perfect pick for foodies. It happens to be located on Restaurant Row in the trendy West Loop, a former meatpacking district turned foodie haven. With its amazing location, this unique Chicago Airbnb is a great pick for a fun weekend getaway with friends.

Step into this two-story vacation home and you’ll be wowed by the towering ceilings, massive floor-to-ceiling windows, and beautiful spiral staircase. With one master suite and two cozy guest bedrooms, this Airbnb can accommodate up to eight guests.

The open-plan great room is perfect for gathering with the group. You can relax on the L-shaped couch in the living room, show off your cooking skills in the luxury kitchen, mix up some cocktails at the wet bar, and host a cocktail hour on the spacious outdoor terrace. There is also a cozy reading nook on the second story where you can read or get some work done. 

Definitely take advantage of the location – some of the city’s best bars and restaurants are right outside your door and downtown is just two minutes away! Be sure to pay a visit to nearby Fulton Market and Randolph Street Market for some excellent dining and shopping.

8. Historic 1894 Home Near Wicker Park 

Best Chicago Airbnbs and Vacation Rentals: Historic Home near Wicker Park
Images courtesy of Airbnb

This beautiful Victorian-style mansion was built in 1894 and is situated near Wicker Park and Bucktown historical district. The 3-bedroom guest suite has been fully remodeled into a comfortable and stylish vacation rental.

Each of the bedrooms features luxury mattresses and linens, smart TVs with Apple TV, and a mini-fridge. If you need extra sleeping space, head up the spiral staircase and you’ll find a loft that can be used as another bedroom. This spacious Airbnb can sleep up to eight guests. 

The dining area features funky vaulted ceilings, large picture windows, and plenty of natural light. The kitchenette has a fridge, coffeemaker, dishes, and a dishwasher. You can prepare basic snacks and heat up leftovers with the microwave. If you feel like having a relaxing night at home, you can order in and dine at the 8-person dining table. 

The neighborhood is easy to explore on foot. Make sure to check out the area’s famous Beer Baron Row and the Robey and Flat Iron buildings. And this Chicago Airbnb is located just steps away from the shops and restaurants on Milwaukee Avenue so the location can’t be beat!

Best Chicago Airbnbs for Large Groups and Events

9. Historic Old Town Penthouse with Private Roof Deck

Chicago Airbnbs and Vacation Homes: Old Town Penthouse
Images courtesy of Airbnb

Located in the heart of Old Town in downtown Chicago, this stunning penthouse loft is right in the center of the action. Both Michigan Avenue and Oak Street Beach are just a short stroll away from your front door! And if you’re planning to host a reunion with family and friends, this is one of the best Airbnbs in Chicago.

This 4,000-square-foot space is comprised of two units that are connected via a private staircase. With five bedrooms, two living rooms, and two kitchens, this loft apartment is ideal for large groups of up to 16. 

This vacation home was built in 1897 and fully renovated in 2017. You’ll love the exposed brick, the 120-year-old barn wood floors, and artsy decorations throughout. You can cook meals for the group in the deluxe kitchens, have a game night in the rustic living rooms, or play pool at the vintage pool table.

One of the standout features of this unique Airbnb is the private roof deck. With 360-degree views of downtown Chicago, the deck is the perfect place to gather with the group! 

10. Tropical Paradise Penthouse in Wicker Park

Best Chicago Airbnbs and Vacation Rentals: Tropical Wicker Park Penthouse
Images courtesy of Airbnb

If you’re looking for the perfect place to host a bachelorette party or a girls’ getaway, this is the Chicago Airbnb for you! With fun tropical-themed art and colorful accents, this 4-bedroom penthouse is chock full of character and designed for entertaining. Plus, it’s located in the heart of Wicker Park, so some of Chicago’s best nightlife venues are right outside your door!

The massive living room is perfect for large groups that want to dance the night away. From the pink shark wall hanging to the neon palm tree wall art, you’ll love the quirky tropical vibes. The owners will even set up four 6-foot dining tables if you want to host a celebratory dinner party! 

The kitchen has everything you need to cook meals at home or mix up cocktails for the group before heading out for a night on the town. Each of the bedrooms is decorated differently and features bold colors, funky decorations, and ultra-comfy beds.

Be sure to bring your camera, because this Insta-worthy vacation rental is definitely one of the most unique Airbnbs in Chicago!

11. Luxury 6-Bedroom Villa in Lincoln Park

Best Airbnbs in Chicago, Illinois: Large Lincoln Park Villa
Images courtesy of Airbnb

This is hands down one of the best Airbnbs in Chicago if you want to go big during your next vacation. With six bedrooms, this luxurious Lincoln Park villa can sleep up to 14 guests, so it’s the perfect pick for a long-awaited reunion with family and friends! 

This Chicago home has so many cool amenities, you might never want to leave. You can have a movie night in the home theater, play ping-pong in the basement playroom, or shoot hoops in the outdoor “sport court.” There’s even a Peloton if you want to get in a workout. 

With multiple living rooms, this Airbnb is designed for hosting large groups. The main great room features a giant sectional sofa with a retractable TV. Head into the chef’s kitchen where you can whip up delicious dinners for the group. Whole Foods, Trader Joe’s, and the Green City Farmer’s Market are all a short walk away in case you need to shop for supplies. 

Foldable doors open up to the large patio where you can warm up around the fire pit, host a barbecue meal, and dine alfresco under the string lights. Head up the spiral staircase where you can relax on the “green roof.”

12. The Armitage: Chic 8-Bedroom Home in Logan Square

Best Chicago Airbnbs and Vacation Rentals: Chic Logan Square House
Images courtesy of Home In Chicago’s Logan Square

The Armitage in Logan Square boasts 6,000 square feet and eight bedrooms so it can sleep up to 16 people. Part of what makes this Chicago Airbnb so unique is that it consists of both the main house and a guesthouse in the private backyard. Plus, it’s located just off of Armitage Avenue (aka the “Second Restaurant Row”) in Logan Square. 

The great room in the main house features 14-foot floor-to-ceiling windows, a comfy leather couch, and chic decor. The space opens up to the gourmet kitchen which is outfitted with everything you need if you want to cook at home. The large breakfast bar makes it easy to socialize while prepping meals. 

When the weather is nice, you’ll love hanging out in the grassy backyard. There’s plenty of space for the kiddos to run around while the adults sit back and relax with a glass of wine.

The Airbnb hosts will go above and beyond to ensure you have the best trip possible. Not only will they give you a list of restaurants and travel recommendations, but they provide complimentary snacks and coffee. If you’re traveling as a large group, you can’t go wrong with this incredible Airbnb!

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That’s it – 12 of the best Airbnbs in Chicago! Do you have a favorite vacation rental in Chicago? Let us know in the comments below.

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  • Nick Wheatley

    Nick took his first solo trip abroad to Ireland and Scotland when he was just 19. Since then he has visited over 70 countries around the world (plus 45 states in the USA).

    He coupled his passion for travel photography with Val’s passion for writing and thus Wandering Wheatleys was born. He now lives in Asheville with his two rambunctious kids, Humphrey and Wilhelminha.

    Besides photography, Nick loves eating the weirdest food he can find in a country (sheep’s brain currently sits in first place) and making Val get up an hour before sunrise to make sure he gets “the good light”.

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