
Chicago Loop vacation rentals
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Top-rated vacation rentals in Chicago Loop
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago Loop vacation rentals
Chicago Loop condo rentals

Evergreen Park Condo with balcony and Jacuzzi tub
The stay was nice and clean and very convenient location.

A Stones Throw from U Chicago South Campus!
Great place and very close to Uchicago!

Entire 3Bed/2Bath Condo Near McCormick & Metro
great stay, very responsive, great place. 100% would stay again

Convenient & Spacious 3BR Condo w/Free Parking
Great place in a quite neighborhood. Close to the convention center and really close to some awesome restaurants.

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
John’s place was clean and cozy. The kitchen was immaculate and we appreciated the nespresso machine and pods. The location was excellent, many food and drink choices right outside the door. It was amazing to have our own parking spot! There are a lot of stairs but that is expected in the city. I would definitely recommend this spot to my friends.

Ultra clean/cozy condo, 10 mins south of Downtown!
Eugene and the Airbnb were incredible! Eugene was extremely professional and responsive. The Airbnb was spotless and beautiful! A great spot to stay.

Near Lake Michigan & Wrigley Field
Brian was a great host very responsive and welcoming. The space is very comfortable, quiet and has everything you need and more. Thank you for the bidets in each bathroom. I still don’t understand how this is not standard in every home. Would definitely stay here again!

Luxurious River North 3BR/2BA- Free Onsite Parking
This place was great and very accommodating for our for our family of 6 (parents & 4 young adult kids). We were able to walk everywhere. Hosts were very communicative and very responsive. And, what a surprise to wake up to a delivery of Stan's Donuts!!! Definitely would recommend this place to anyone visiting Chicago.
Other great vacation rentals in Chicago Loop

Family Friendly Duplex/9 min from MDW/Free Parking
Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.

Enamored in Elmhurst
This home was perfect. I would highly recommend this place.

Condo with private terrace, free WIFI and parking
We have traveled to Chicago with a party of 5 - 3 adults and 2 kids in February 2025. We stayed for 3 nights and really liked Mark's place. It is really bigger than it shows on the pictures, so it really accomodates 6-8 people easily. Host was responsive and provided helpful and timely instructions. Would stay again.

Elegant 4Bedroom with Free Parking in Albany Park
Wonderful stay as always, thank you so much!

City Gem: Stylish 3BR for Urban Explorers
Was a nice comfortable place.

Spacious condo with open floor plan and fireplace
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.

Spacious whole apt near shopping and city
The BNB was in a convenient spot and Daniel was very communicative and helpful. I enjoyed my stay!

Spacious Home in Chicago Suburbs
The space was well decorated, spacious and perfect for our family. I really appreciated the fact that the house was nice and warm once we arrived considering the Chicago winter. Our family was able to be comfortable and enjoy our stay with no major issues.
Quick stats about vacation rentals in Chicago Loop
Total rentals
1.1K properties
Total number of reviews
27K reviews
Family-friendly rentals
290 properties are a good fit for families
Pet-friendly rentals
610 properties allow pets
Rentals with a pool
510 properties have a pool
Rentals with dedicated workspaces
670 properties have a dedicated workspace
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