21 Best Chicago Airbnbs for Your Next Windy City Trip (2022)

A professional-grade kitchen is the main draw of this Airbnb rental, but the collection of rare teas and a Japanese soaking tub are close runners-up. With one bedroom, it’s best for couples looking to cozy up for a long weekend getaway or a solo traveler looking for some peace and quiet. The interiors are full of soft earth tones, wooden accents, and plenty of art. But the dining table is the place to gather, converse, and enjoy a delicious meal at the end of the day.

Situated near the famed Lincoln Park Zoo, this three-bedroom home is located right in the historic Old Town Triangle. Think tons of Victorian buildings, tree-lined streets, cafés, and boutiques to check out. But back to the Airbnb, which is a pristine example of Craftsman-style architecture. There’s also a private chef available on request, for extra special occasions. Speaking of extras, guests also have access to two bicycles to use during their stay, perfect for cruising down the nearby Lake Michigan bike path.

This Airbnb rental is testing the limits of just how high ceilings can be. The airy vibes are only taken further with a floor-to-ceiling window wall leading to an outdoor patio area. The three-bedroom home is located right in the center of an incredible food scene: the West Loop. Write it down, and make sure to plan an entire week of meals in this area’s Restaurant Row.

You can’t go wrong with a stay in Logan Square, thanks to its proximity to Wrigley Field, the 606 Trail, and the downtown neighborhoods. With four bedrooms and six beds, this home has enough room to sleep 16 people—that is, if some don’t mind crashing on a couch. It’s the ideal spot to come down from post-cheering on the home team (the Cubs, of course) or rest your feet after a day of architecture peeping. Amenities include central air conditioning, free parking, a private patio, WiFi, and an on-site washer and dryer.

This three-bedroom rental unit is housed in a building that dates back to 1886. The third-floor walk-up has been renovated, but the old-school charm remains in its hardwood floors, ample windows, and brick façade. This Airbnb has also been applauded for its popular amenities, like a washer and dryer, Wi-Fi, dishwasher, travel crib, bathtub, and patio. Don’t miss the opportunity to walk by one of the only homes to survive the Great Chicago Fire of 1871, located on the same block.

Welcome to the three-bedroom Roscoe House—an updated 1888 Victorian home that effortlessly blends the best of both modern and vintage design. With a stainless-steel kitchen featuring all-star appliances, this Airbnb Chicago rental is the perfect setup for your next city escape. Right by Wrigley Field and Southport Street, this prime location boasts family-friendly restaurants and shops ideal for you and a group. Do note that there is a nearby train track that requires maintenance from time to time. Your hosts, however, will be able to keep you posted on the work schedule so you can prepare for any noise.

Wake up to a sun-drenched space in this Edgewater Glen home. Picturesque windows anchor the thoughtfully-designed living space, and an open concept floor plan nicely contrasts the dark wood tones lining the residence. Conveniently located near plenty of public transportation, loads of neighborhood shops, and even beautiful beaches, this vacation rental provides the best of both worlds for travelers hoping to stay in the thick of Chicago while still finding solace and respite. 

Those with an eye for design will feel right at home in this studio guesthouse. From the trendy seating to the claw-foot bathtub surrounded by plants, walking into this space is like letting out a big exhale. This studio was once a machine shop, but you’d never guess its history thanks to the squeaky-clean color palette and midcentury furniture. Staying here drops you in the heart of the Humboldt Park neighborhood, and Wicker Park is a leisurely stroll away.

Luxury meets ease in this 2,500-square-foot penthouse located in the heart of the vibrant West Loop neighborhood. With three bedrooms, 15-foot ceilings, and brick-lined walls, this rental is ideal for larger groups looking to relax with a sky-high view of all Chicago has to offer. Located on the top floor of a historic 1920s building right by Fulton Market, this prime Airbnb is great for entertaining. With a grand open living space and ample natural light—thanks to a corner unit location—you can’t go wrong opting into a stay at this luxe rental. 

Step inside your next vacation rental and soak up all this home has to offer. From your own rooftop equipped with a jacuzzi, a king bed, and spacious seating area, to an indoor steam shower and cozy entertainment center, this luxurious Airbnb is ready to be booked. Given the property’s great location and endless amenities, it’s no wonder it’s rented by a Superhost—a highly rated and experienced Airbnb host committed to providing the best of the best. Located in one of Chicago’s trendiest neighborhoods, this Wicker Park spot is definitely one to add to your list. 

Just one neighborhood away from Wrigleyville, otherwise known as home to the infamous Chicago Cubs, sits a cozy Uptown rental with nine bedrooms. Downtown Chicago, Evanston, and Lake Shore Drive are easily accessible by train from this sought-after spot. Right off the shores of Lake Michigan, the Uptown neighborhood boasts an incredibly diverse food scene featuring Vietnamese, Ethiopian, Chinese, and Pakistani gems that are all worth checking out. This renovated century-old home is adorned with parquet flooring, original architectural details, and an inviting ambiance ready to greet you after a long day of sightseeing. 

With four bedrooms, this art-filled home is great for larger groups. A spacious living room makes for a central gathering place, while each bedroom is equipped with memory foam mattresses when the crew splits off to recharge for the night. This rental has everything you’d want when it comes to Chicago vacation rentals—self check-in, free parking on premises, washer and dryer, TV, and a dishwasher. Plus, pets are allowed to stay with you. The location can’t be beat: You’re a 10-minute drive from Lincoln Park, which is home to a zoo, the Chicago History Museum, Lincoln Park Conservatory, North Avenue Beach, and tons of other attractions travelers of all ages will love.

Each room seamlessly transitions to the next in this airy one-bedroom rental. A separate study has been set up for those who need to take a break from vacation to check in on work, while a light-filled dining area gives you a bird’s-eye view over the rest of the neighborhood. Located in the popular Logan Square neighborhood, you’ve got easy access to theaters, parks, restaurants, bars, cafés, shopping, and more. No matter how you choose to fill your day, wind down with a cocktail and a vinyl session in your rental’s living area.

If you’re searching for peace and quiet, look no further than this quaint farmhouse-inspired rental. Although it’s located in an up-and-coming, active neighborhood near Downtown Chicago, you’ll be comfortably tucked away in this walkable and family-friendly locale. Only 20 short minutes away from the O’Hare International Airport, this cozy, two-bedroom oasis is just perfectly secluded while still only moments away from the hustle and bustle of lively Chicago. 

Craving a movie night in a private screening room? What about staying in a former picture frame factory? This three-bedroom Airbnb, hosted by architect Aaron, provides all of the above and more. Situated in the River West neighborhood of Chicago, this rental is a quick walk away from sights like Wicker Park and Buck Town. Plenty of coffee shops, restaurants, and bars await you while an easily manageable subway system is only two minutes from your door. 

You’ll find this studio apartment right between South Old Irving and Kilbourn parks, right off North Milwaukee Avenue, which is known for its craft beer and cocktail scene. Equipped with all of the creature comforts of home (air-conditioning, free parking, Wi-Fi, and a full kitchen, to name a few), you’re less than a 20-minute drive from O’Hare International Airport and Logan Square, which has some of the city’s best nightlife options. The swinging chair adjacent to the queen bed is another great spot to relax and recharge.

If you want to settle into the city’s most energetic neighborhood, check out this two-bedroom pied-à-terre. The Magnificent Mile is one of the best shopping destinations in Illinois and home to restaurants you won’t soon forget. Though there’s plenty to do in the area, you’re also a quick drive, walk, or train ride from Navy Pier, Millennium Park, and the Gold Coast. When you need a break from seeing the sights, your chic apartment has a full-size kitchen, Smart TV, and a cozy living area calling your name for homemade dinner and a movie night.

Fans of rock and roll will love this two-bedroom apartment in the River North neighborhood. Decorated with instruments and memorabilia, it’s almost like walking into your own personal museum. When you’re ready to pry yourself away from the decor, you’re minutes from the Magnificent Mile for shopping, plus the South Loop neighborhood and Millennium Park (if you’re up for a longer stroll). Architecture buffs shouldn’t miss the quick drive or long walk to the Old Town neighborhood—the quaint streets and Victorian architecture shouldn’t be missed. Once you’re ready to wind down for the day, grab a glass of wine and kick back to a soundtrack of vinyl before retreating to the canopy bed to recharge.

The mix of modern and vintage furniture throughout this two-bedroom loft in the Pilsen neighborhood is enough to mark it on your Chicago wishlist. Enjoy your morning coffee or tea on the private back porch, or settle into the living room with a good book. Your reservation also gets you one free parking spot for added convenience. While the home is located near lots of restaurants, cafés, bars, and shopping, you’re also close to plenty of public transit options that can get you downtown in a flash.