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Vacation rentals in Chicago Loop
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Chicago Loop
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Popular amenities for Chicago Loop vacation rentals
Other great vacation rentals in Chicago Loop
Guest favorite
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Home in West Lawn
4.94 out of 5 average rating, 34 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
NoelleRating, 5 stars1 week ago
Loved our stay in Chicago! Johanna was a WONDERFUL host!! Very helpful and very clear instructions for check in and out. When I needed to get ahold of her it was super easy to connect with her. House is adorable and very home like feeling :) would definitely recommend staying here!
Guest favorite

Home in Elmhurst
4.83 out of 5 average rating, 18 reviewsEnamored in Elmhurst
MarieRating, 5 stars3 weeks ago
So happy this was available for a last minute trip to Elmhurst — very comfortable and clean! Easy to get around the area and Mark was easy to communicate with and responsive!
Guest favorite

Apartment in West Town
4.85 out of 5 average rating, 126 reviewsCondo with private terrace, free WIFI and parking
AaronRating, 5 stars6 months ago
Great place, very clear and easy instructions, close to everything you need in the city, made a mistake with booking and they made it extremely easy and very flexible to stay an extra night.
Guest favorite

Home in Chicago
4.92 out of 5 average rating, 12 reviewsA home away from home.
NicoleRating, 5 stars5 months ago
Me my freinds and family enjoyed our stay. The host was very quick to respond to any concerns. The home was clean and spacious. The decor was nice to take pictures. I liked that it had a bathroom downstairs for easy assess. We will come back when we visit Chicago again. Thanks you guy you were awesome.
Guest favorite

Apartment in Albany Park
4.95 out of 5 average rating, 39 reviewsElegant 4Bedroom with Free Parking in Albany Park
MatthewRating, 5 stars1 month ago
Thank you for letting us stay in your beautiful home. Everything was exactly as described! Will definitely stay again
Superhost
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Apartment in Jefferson Park
4.81 out of 5 average rating, 16 reviewsCity Gem: Stylish 3BR for Urban Explorers
MaríaRating, 5 stars2 months ago
Excellent lodging and host, I would come back!
Superhost

Home in Logan Square
4.86 out of 5 average rating, 90 reviewsCalifornia Cottage/4br prime location Logan Square
JoelRating, 5 stars1 month ago
This truly was an excellent deal for all of the space and the location. The beds were comfy. The layout has great communal space. Very clean and well maintained. We would definitely stay here again.
Superhost

Condo in East Rogers Park
4.79 out of 5 average rating, 29 reviewsSpacious condo with open floor plan and fireplace
TatianaRating, 5 stars1 month ago
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.
Quick stats about vacation rentals in Chicago Loop
Total rentals
1K properties
Total number of reviews
28K reviews
Family-friendly rentals
290 properties are a good fit for families
Pet-friendly rentals
580 properties allow pets
Rentals with a pool
450 properties have a pool
Rentals with dedicated workspaces
710 properties have a dedicated workspace
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