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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.

  • 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:

    “It was nice, stylish, and clean! Unbeatable price! Parking spot was an added bonus! Neighbors can be a bit too loud if you’re trying to find some peace and quiet.”

  • Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots
    SUPERHOSTEntire loft · 4 guests · 2 beds · 2 baths
    Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots

    Luxury Wrigleyville loft in one of the best areas of Chicago. ONE block from public transportation that can take you to the downtown area. Very safe neighborhood that has families and fun. Experience Chicago like a local.

    What guests are saying:

    “Awesome spot! We stayed with 3 adults and it was very comfortable. The area is really safe and the parking spot in the back is super convenient! We were close to public transportation though we ended up not needing to use it since the parking spot allowed us to drive around the city easily. We were within walking distance to many restaurants. We cooked a few meals in the apartment and the kitchen had everything we needed for pots and utensils, etc. As noted in the description, it is a 3rd floor walk-up so keep that in mind if you have anyone traveling with you that may struggle with that (we didn't have any issue with climbing the stairs at all, so if you're in good health, it's not a problem). I think the price is really great for the area. I did a ton of research before booking our trip to Chicago and this place is definitely a great deal!! Communication was great and effortless! Highly recommended!”

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:GYD28,727 / night
Enjoy Chicago’s Nightlife from Studio Apartment
SUPERHOSTEntire apartment
Enjoy Chicago’s Nightlife from Studio Apartment
Price:GYD11,142 / night
Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOSTEntire apartment
Basement Studio w/Free St. Parking, Humboldt Park
Price:GYD9,402 / night
Stunning Retro Apartment in Andersonville
SUPERHOSTEntire apartment
Stunning Retro Apartment in Andersonville
Price:GYD17,723 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:GYD31,617 / night
Shared Artist Loft Own Private Room
SUPERHOSTPrivate room
Shared Artist Loft Own Private Room
Price:GYD20,892 / night
Unwind in the Bath at a Hip, Historic Coach House
SUPERHOSTEntire guesthouse
Unwind in the Bath at a Hip, Historic Coach House
Price:GYD21,241 / night
Bright, Modern Apartment in a Vintage Greystone
SUPERHOSTEntire apartment
Bright, Modern Apartment in a Vintage Greystone
Price:GYD26,116 / night
Eclectic and Colorful Retro Apartment near Logan Square
SUPERHOSTEntire apartment
Eclectic and Colorful Retro Apartment near Logan Square
Price:GYD21,310 / night
Sonder | Essex on the Park | Ideal 1BR + Pool
Entire apartment
Sonder | Essex on the Park | Ideal 1BR + Pool
Price:GYD61,877 / night
Private Room in Bridgeport Home
SUPERHOSTPrivate room
Private Room in Bridgeport Home
Price:GYD13,580 / night
The Buck Stop
SUPERHOSTEntire apartment
The Buck Stop
Price:GYD20,126 / 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