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Vacation rentals in Chicago

Vacation rentals in Chicago

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Sonder | Essex on the Park | Ideal 1BR + Pool
    Entire apartment · 4 guests · 2 beds · 1 bath
    Sonder | Essex on the Park | Ideal 1BR + Pool

    Whether you are just getting away for the weekend or looking for an extended stay, we’re committed to creating comfortable experiences for our guests. We offer contact-free check-in and 24/7 virtual support which limits in-person interaction. In addition to following the guidance of the CDC and the World Health Organization, we’re partnering with sanitization experts at the Cleveland Clinic to ensure that all of our cleaning standards follow the advice of leaders in the field. We’ve put safety seals on high-touch items, stocked all spaces with complimentary hand sanitizer, and added social distancing signage in common areas. Each space is carefully designed and run by us, so you’ll always know what to expect. - Digital check-in - Professionally cleaned - 24/7 virtual concierge via text, email,or phone - Private all-in-one living spaces (ample work space) - Utilities included (even for longer stays) - Coffee, fresh towels, and bathroom essentials provided Sonder has hosted millions of guests in 5,000+ spaces worldwide with an average rating of 4.6 stars. It was named the most innovative travel company by Fast Company in 2019. Note: To protect your safety, building amenities are subject to availability and may be temporarily closed. Please check the “other things to note” section for specific updates about this building.

    What guests are saying:

    “We had a terrific stay in this modern, open apartment. The interior is stylish and super clean and the views from the floor to ceiling windows were amazing, from sunrise to moon rise over the lake. The neighborhood has plenty to offer and was fairly quiet when we were there. It is a walk to the more central parts of the city but we did not mind that. Check in and out couldn't have been easier.”

  • Modern Chicago Loft with a Complimentary Garage Spot
    SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
    Modern Chicago Loft with a Complimentary Garage Spot

    Dine by the natural wood breakfast bar or on the rooftop deck. This classy loft boasts open-plan living, exposed brickwork and stunning artwork. Check out our other available listings within the same building by clicking below on our host profile.

    What guests are saying:

    “This place was perfect for my boyfriend and I on our 2 night stop in Chicago! It’s super stylish and cozy, and the bed is super comfortable. We visited the main sights in Chicago by bike - it was the perfect location!”

  • Hip Chicago Apartment - FREE Parking Spot Included
    SUPERHOSTEntire apartment · 4 guests · 2 beds · 1 bath
    Hip Chicago Apartment - FREE Parking Spot Included

    You’ll love this high-end, newly renovated 2 bedroom apartment located in Chicago’s iconic Logan Square. This bright and modern space has free parking, a fully equipped stainless-steel kitchen and an outdoor sitting area perfect for a sunny meal. Walking distance from a bike rental station and hip Armitage Street where you can find a wide selection of restaurants and bars to suit any palate. You’ll also be close by the 606 Trail, a lovely place to enjoy a walk, bike or go for a run

    What guests are saying:

    “I really enjoyed my stay at Alex and Leo’s place. Check-in was a breeze, great communication from the hosts, the bed was super comfortable, kitchen had all the necessary items, great TV, and comfy sofa, and the location is excellent with lots of fun places to walk. I highly recommend this place.”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chicago vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Chicago

Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment
Best in Chicago, private, amazing garden space
Price:$135 / night
Walk to Lake Michigan From a Contemporary Uptown Haven
SUPERHOSTEntire apartment
Walk to Lake Michigan From a Contemporary Uptown Haven
Price:$70 / night
Logan Square Lookout
SUPERHOSTEntire apartment
Logan Square Lookout
Price:$44 / night
Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots
SUPERHOSTEntire loft
Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots
Price:$137 / night
Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOSTEntire apartment
Basement Studio w/Free St. Parking, Humboldt Park
Price:$45 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:$158 / night
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
SUPERHOSTEntire apartment
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
Price:$46 / night
Spacious Serene En Suite, Incredible Loop Location
SUPERHOSTPrivate room
Spacious Serene En Suite, Incredible Loop Location
Price:$51 / night
Stunning Retro Apartment in Andersonville
SUPERHOSTEntire apartment
Stunning Retro Apartment in Andersonville
Price:$89 / night
Shared Artist Loft Own Private Room
SUPERHOSTPrivate room
Shared Artist Loft Own Private Room
Price:$101 / night
Private Room/Bath Wicker Park, Free Street Parking
SUPERHOSTPrivate room
Private Room/Bath Wicker Park, Free Street Parking
Price:$40 / night
Unwind in the Bath at a Hip, Historic Coach House
SUPERHOSTEntire guesthouse
Unwind in the Bath at a Hip, Historic Coach House
Price:$101 / night
Show all

Learn more about Chicago

What types of vacation rentals are available in Chicago?

Here in Chicago, there are plenty of options for places to stay. Here are a few examples:
  • Apartments (4,696 rentals)
  • Houses (1,150 rentals)
  • Guest suites (242 rentals)

Are there apartments with WiFi?

Who doesn’t want WiFi in their apartment? Here in Chicago, you’ll find 4,531 apartments that have WiFi.

What area should I stay in when traveling to Chicago?

Every area of Chicago is unique. So where should you stay? Let the locals help you decide. These are their top recommendations:
  • Lakeview (418 rentals)
  • Logan Square (340 rentals)
  • River North (325 rentals)
  • Loop (306 rentals)
  • Lincoln Park (258 rentals)

What are the top attractions in Chicago?

Locals agree that these attractions are worth a visit:
  • The Art Institute of Chicago (363 rentals)
  • Lincoln Park (138 rentals)
  • Wrigley Field (750 rentals)
  • Navy Pier (99 rentals)
  • Field Museum of Natural History (144 rentals)

What are some kid-friendly activities in Chicago?

Locals agree—these are all great places to take the kids:
  • Lincoln Park
  • Wrigley Field
  • Shedd Aquarium
  • Field Museum of Natural History
  • Museum of Science and Industry

What are the top places to eat in Chicago?

Whether you’re looking for a tasty treat or a hearty meal, here’s where the locals say to go:
  • Big Star
  • Longman & Eagle
  • Revolution Brewing
  • Parson's Chicken & Fish
  • Au Cheval