Apartment holiday rentals in Downtown Chicago

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Popular amenities for Downtown Chicago apartment rentals

Weekly apartment rentals

Guest favourite
Flat in Chicago
4.89 out of 5 average rating, 35 reviews

Spacious w. Pool, gym, free gift. Sleeps 4

FriederikeRating, 5 stars2 weeks ago
Thank you so much. Looking forward to staying at your place again.
Flat in Chicago
5 out of 5 average rating, 3 reviews

Sunny Penthouse - Oakwood Beach

DeannaRating, 5 stars4 days ago
Manny and Veronica have a beautiful apartment and were amazing hosts! They helped with any issues and were more than accommodating of me and the 3 other guests I booked with! Communication was quick and if I needed anything, they were more than ready to assist. The apartment is really spacious, supurb natural lighting, great appliances, and is decorated in such a way that it feels very homey. It's a 5 minute drive from a great grocery store and restaurants are not that far in a very comfortable and safe feeling area. It was a great place to come back to after spending the day out and about, I highly recommended staying here if you want a super nice and comfortable Chicago stay!
Guest favourite
Flat in Chicago
5 out of 5 average rating, 8 reviews

*NEW* West Loop GreenLine 1br w/Backyard-near CTA

UjunwaRating, 5 stars1 week ago
Azam was a great and responsive host. He accommodated all of our needs and always checked in appropriately to make sure we were doing okay. He was kind in his actions and flexible with our requests. I felt safe whenever I walked to the Station or around the neighborhood. A great place, would definitely recommend to my friends and family.
Flat in Chicago
4.69 out of 5 average rating, 132 reviews

Cozy 1BR in South Loop | Convenience in the City

DavidRating, 5 stars3 months ago
Great place to stay! Can get anywhere in the city, its right off the "L". Not far from Michigan Ave, either. Would highly recommend this place to anyone who is traveling to Chicago.
Flat in Chicago
4.83 out of 5 average rating, 249 reviews

Spectacular Corner 2BR Penthouse in the Loop | Roo

MikeRating, 5 stars1 week ago
Fantastic location a block from the riverwalk and two blocks from Millennium park, stunning views from large windows in every room, and very convenient short walks to sites, eats, and drinks. Great apartment with two large bedrooms with queen beds, two large bathrooms, and roomy and brightly-lit living and kitchen areas. Easy access through 24-hour security and a fast elevator to the penthouse. Would love to stay here again.
Flat in Chicago
4.8 out of 5 average rating, 300 reviews

Kasa | Studio, Walk to Grant Park | South Loop

AlekseiRating, 5 stars5 days ago
Great place to stay while visiting inner Chicago with a small dog. Easy check-in and check-out, responsive host. Parking garage and small green space nearby as well. Would definitely recommend.
Flat in Chicago
4.7 out of 5 average rating, 277 reviews

Sonder Onterie | King Studio Apartment

KatieRating, 5 stars2 weeks ago
My boyfriend and I stayed here for two nights, it was the perfect spot if you’re looking to stay close to downtown. Everything was within walking distance, the bed was comfortable and everything was clean. The code was provided with plenty of time and we had no issues. We would definitely stay here again!
Guest favourite
Flat in Chicago
5 out of 5 average rating, 9 reviews

Luxury 2BD/2BA High Rise with Views, Gym, Rooftop

ViyadaRating, 5 stars2 weeks ago
The unit looks better than what we’ve expected. The room is clean and neat. The apartment is also closed to the city center, which allow us to easily access many tourist attractions. Christian is also very friendly host and willing to help you out with anything.

Private apartment rentals

Guest favourite
Flat in Chicago
4.95 out of 5 average rating, 149 reviews

Cute, Clean, Cozy Apartment in Pilsen

EnriqueRating, 5 stars3 weeks ago
I had a wonderful stay at this cozy garden apartment! The space was exactly as described—clean, comfortable, and thoughtfully set up with everything I needed. I especially appreciated how quiet and peaceful the neighborhood was, yet still close to everything. The location made it easy to get around, but it also felt like a relaxing retreat after a busy day. The setting added a nice touch of charm and tranquility. I’d definitely stay here again—highly recommended!
Guest favourite
Flat in Chicago
4.86 out of 5 average rating, 113 reviews

Breathtaking & Chic Oasis Loc in Desirable Old Twn

DeniseRating, 5 stars3 weeks ago
I loved everything about my stay ! Very nice and clean and the host were amazing
Superhost
Flat in Chicago
5 out of 5 average rating, 4 reviews

Modern & Spacious Condo Minutes from the Loop

AlanRating, 5 stars2 weeks ago
Absolutely loved our stay. Great location! Super comfortable beds. Slept like a baby. Felt like home. Parking felt very secure. No problems at all. We will look forward to staying here again!
Guest favourite
Flat in Chicago
4.98 out of 5 average rating, 47 reviews

Old Town Tranquility (+parking)

SusanRating, 5 stars2 weeks ago
Nicole & Matt were responsive, kind, & timely communicators! Their special oasis was artistically beautiful & comfortable in a walkable, safe & vibrant space! We met a neighbor who taught us all about the neighborhood's unique history! We loved traveling all over Chicago in this home away from home! You will, too!
Guest favourite
Flat in Chicago
4.95 out of 5 average rating, 64 reviews

Flor de Luna ~ Little Village Chicago Retreat

CameronRating, 5 stars2 weeks ago
This place was so cute and felt like home. Had everything you would need! She provided places to eat, visit & more! would recommend for a group of 2-4 friends or even a smaller family! Loved it here!!
Guest favourite
Flat in Chicago
4.91 out of 5 average rating, 209 reviews

The South Loop Reserve I Sleep 6 I Top Rated

DavidRating, 5 stars4 days ago
We had a fantastic stay! The apartment looked exactly like the pictures( even better in person)—clean, stylish, and very spacious. It was comfortable and had everything needed for a relaxing visit. The location was also perfect—just a 10 -12 minute easy trip to downtown Chicago, making it super convenient for exploring the city. I’d definitely stay here again!
Guest favourite
Flat in Chicago
4.91 out of 5 average rating, 23 reviews

City Views from a 2-BR Balcony Apartment

RobertRating, 5 stars1 week ago
Just like description. Great modern place. Host responded right away to all questions and needs. Would highly recommend.
Flat in Chicago
4.77 out of 5 average rating, 35 reviews

Level Studio | Fulton Market

KimRating, 5 stars1 month ago
This was the perfect place to stay in Chicago! Everything was nearby and the hosts were very friendly and responsive. The amenities provided were the best part; I enjoyed the rooftop, hot tub, and the views! I will be staying here again (:

Apartment rentals with a hot tub

Guest favourite
Flat in Chicago
4.98 out of 5 average rating, 103 reviews

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis

BriantRating, 5 stars2 weeks ago
We stayed on the third floor of the complex and enjoyed Matthew's attention to detail. He gave a lot of thought to all components of his property.
Superhost
Flat in Chicago
4.92 out of 5 average rating, 48 reviews

The Areal Oasis

JenniferRating, 5 stars3 weeks ago
What a spectacular stay! We thoroughly enjoyed our time at Stephanie's "Areal Oasis". Apartment was spotless, well decorated, very well furnished, and the view is spectacular. Stephanie was an excellent communicator and always very responsive. We thoroughly recommend staying here and hope to return.
Superhost
Flat in Chicago
4.85 out of 5 average rating, 78 reviews

Spacious Beautiful Condo

SophiaRating, 5 stars2 days ago
We came for our daughter’s graduation and stayed a few extra days to tour the city. This place was perfectly located for both occasions. It was much more spacious than we expected, and everything was very clean. We especially appreciated the fresh towels and beddings. Our only wish is that the beds were a bit larger, especially the double bed, which would be more comfortable for a couple if it were at least a queen size. That said, the beds were very comfortable. Overall, we had a wonderful stay - definitely one of our best Airbnb experiences!
Superhost
Flat in Chicago
4.83 out of 5 average rating, 54 reviews

Rooftop HotTub As Seen On "Married At First Sight"

KimikoRating, 5 stars8 months ago
I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!
Guest favourite
Flat in Chicago
4.96 out of 5 average rating, 27 reviews

Skyline Oasis: City & Lake Views

NatalieRating, 5 stars2 weeks ago
Perfect weeklong stay in Chicago! The apartment is well equipped and makes you feel right at home. The building is connected via sky bridge to Jewel making it easy to grab groceries. The location cannot be beat - easy access to West Loop, Wicker Park, River North. The hosts were fantastic and flexible with our check in times. Looking forward to coming back!
Top guest favourite
Flat in Chicago
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars4 weeks ago
We stayed with my family for 3 days n loved the place it's ambience, cleanliness, very well equipped with all the necessities.....this place definitely feels like home and the hosts are very kind and quick with there response. Wherever in future I am coming to chicago shall book this place.
Superhost
Flat in Chicago
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars1 week ago
David and his co-host were excellent. Our family enjoyed our stay. We used to live in the Bronzeville area and love the new additions to the neighborhood. Everything met or exceeded our expectations.
Superhost
Flat in Chicago
4.69 out of 5 average rating, 49 reviews

Sentral 1 Bedroom Apt in South Loop Chicago

RichardRating, 5 stars1 week ago
Sentral worked great for us going to a graduation for a long weekend. Unit is exactly as described, modern, and clean. Kitchen utensils are reasonable while shelves and refrig are empty save for some coffee so if going to cook/eat be sure to bring everything such as butter, spices, etc. - a Trader Joes is 3 blocks away. Price is not cheap but is very convenient and easy so on balance okay for us. Front desk is very helpful and cheerful.

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