Vacation rental apartments in Chicago
Book downtown vacation rental apartments, houses, and more on Airbnb
Top-rated apartments in Chicago
Guests agree: these stays are highly rated for location, cleanliness, and more.
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.
“The place was super clean. Literally the cleanest airbnb I’ve ever stayed at. Super easy to check in and out. The hosts were also easy to get in contact with and they made sure to check in to see if everything was fine after we arrived. Would definitely stay again!”
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
“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.”
This amazing apartment is located in the Little Village community in Chicago. Little Village is the heart of the Mexican community because it's vivid representation of the Mexican culture. In addition, the apartment is close to two Chicago parks where you can enjoy a walk or a bike ride.
“Paul’s place was beautiful! My husband and I loved the neighborhood, and had a wonderful stay. Everything was exceptional. Can’t wait to stay again next time we return to Chicago! We miss our feline friend Abu already!”
Learn more about Chicago
What types of vacation rentals are available in Chicago?
What types of vacation rentals are available in Chicago?
- Apartments (4,696 rentals)
- Houses (1,150 rentals)
- Guest suites (242 rentals)
Are there apartments with WiFi?
Are there apartments with WiFi?
What area should I stay in when traveling to Chicago?
What area should I stay in when traveling to Chicago?
- 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?
What are the top attractions in Chicago?
- 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?
What are some kid-friendly activities in Chicago?
- 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?
What are the top places to eat in Chicago?
- Big Star
- Longman & Eagle
- Revolution Brewing
- Parson's Chicken & Fish
- Au Cheval