Chicago Loop vacation rentals

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Popular amenities for Chicago Loop vacation rentals

Stay near Chicago Loop's top sights

Millennium Park1,243 locals recommend
Navy Pier933 locals recommend
University of Illinois at Chicago27 locals recommend
Shedd Aquarium673 locals recommend
Northerly Island45 locals recommend
The Field Museum657 locals recommend

Chicago Loop condo rentals

Superhost
Condo in Evergreen Park
4.81 out of 5 average rating, 115 reviews

Evergreen Park Condo with balcony and Jacuzzi tub

KindallRating, 5 stars2 months ago
The stay was nice and clean and very convenient location.
Guest favorite
Condo in Woodlawn
4.88 out of 5 average rating, 228 reviews

A Stones Throw from U Chicago South Campus!

ThomasRating, 5 stars1 month ago
Great place and very close to Uchicago!
Guest favorite
Condo in Bridgeport
4.95 out of 5 average rating, 123 reviews

Entire 3Bed/2Bath Condo Near McCormick & Metro

AlisonRating, 5 stars4 weeks ago
great stay, very responsive, great place. 100% would stay again
Guest favorite
Condo in Bridgeport
4.9 out of 5 average rating, 109 reviews

Convenient & Spacious 3BR Condo w/Free Parking

DanRating, 5 stars4 weeks ago
Great place in a quite neighborhood. Close to the convention center and really close to some awesome restaurants.
Guest favorite
Condo in Lincoln Park
4.91 out of 5 average rating, 100 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

KendraRating, 5 stars2 months ago
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.
Guest favorite
Condo in Chicago
4.93 out of 5 average rating, 150 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

JazminRating, 5 stars3 days ago
Eugene and the Airbnb were incredible! Eugene was extremely professional and responsive. The Airbnb was spotless and beautiful! A great spot to stay.
Top guest favorite
Condo in Uptown
4.98 out of 5 average rating, 263 reviews

Near Lake Michigan & Wrigley Field

RandalRating, 5 stars5 days ago
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!
Guest favorite
Condo in River North
4.98 out of 5 average rating, 128 reviews

Luxurious River North 3BR/2BA- Free Onsite Parking

DaraRating, 5 stars2 months ago
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

Superhost
Home in West Lawn
4.94 out of 5 average rating, 36 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

AshleyRating, 5 stars1 week ago
Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.
Guest favorite
Home in Elmhurst
4.86 out of 5 average rating, 21 reviews

Enamored in Elmhurst

LatoyaRating, 5 stars1 week ago
This home was perfect. I would highly recommend this place.
Guest favorite
Apartment in West Town
4.85 out of 5 average rating, 127 reviews

Condo with private terrace, free WIFI and parking

OlegRating, 5 stars1 month ago
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.
Top guest favorite
Apartment in Albany Park
4.95 out of 5 average rating, 41 reviews

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars1 month ago
Wonderful stay as always, thank you so much!
Superhost
Apartment in Jefferson Park
4.67 out of 5 average rating, 21 reviews

City Gem: Stylish 3BR for Urban Explorers

BaileeRating, 5 stars3 weeks ago
Was a nice comfortable place.
Superhost
Condo in East Rogers Park
4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars2 months 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.
Superhost
Home in Cicero
4.78 out of 5 average rating, 174 reviews

Spacious whole apt near shopping and city

ChristopherRating, 5 stars1 month ago
The BNB was in a convenient spot and Daniel was very communicative and helpful. I enjoyed my stay!
Top guest favorite
Home in Lombard
5 out of 5 average rating, 23 reviews

Spacious Home in Chicago Suburbs

ClydeRating, 5 stars1 month ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Chicago Loop