Vacation rental apartments in Chicago

Book downtown vacation rental apartments, houses, and more on Airbnb

Top-rated vacation rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

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:
“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.”
From G$14,029 / night
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!”
From G$11,641 / night
SUPERHOSTEntire apartment · 4 guests · 2 beds · 1 bath
Logan Square Lookout
Great top floor apartment along a tree lined street with free street parking. Has a cozy small bedroom with a spacious living room and kitchen. On Site Coin operated laundry. Great back yard with garden area. This is in the super nice Logan Square neighborhood with cool bars and award winning restaurants. Friendly safe neighborhood with lots to do. Quick walk to the Blue Line gets you Downtown or out to O'Hare. I own the building which consists of 3 apartments. So I'm always nearby.
What guests are saying:
“I stayed at Patrick’s place for about 2 weeks while I was in town for work and the apartment couldn’t have been better! I never had to park more than a block away for parking, there’s a cool bar right on the corner of the block, and it is located only a short drive to pretty much anywhere you would want to go in Chicago. Neighborhood is nice and quiet and neighbors are super friendly. Patrick is also extremely responsive with messages and would check in periodically to ensure that everything was still going smoothly or to see if I needed anything. I can’t recommend this place enough! You’d be hard pressed to find a better location for the value!”
From G$9,882 / night