Apartment holiday rentals in Chicago Loop

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Popular amenities for Chicago Loop apartment rentals

Weekly apartment rentals

Guest favourite
Flat in South Loop
4.88 out of 5 average rating, 34 reviews

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

AdrianRating, 5 stars2 weeks ago
Location, location, location!! Everything was within a 10-minute walk, with lots of restaurants, coffee spots and stores nearby. The place itself was amazing! Very clean and a very responsive host. Highly recommend!
Top guest favourite
Flat in Bridgeport
5 out of 5 average rating, 11 reviews

Designer Garden Unit in Bridgeport

ChristineRating, 5 stars3 days ago
Beautiful trendy place in the heart of Bridgeport. Went home to visit family and felt at home! Loved our stay and will definitely return. Thank you Wood
Flat in South Loop
4.66 out of 5 average rating, 89 reviews

The Landing @ South Loop

CerriRating, 5 stars1 month ago
This was the perfect location! Trader Joe’s, Bus, cafe with delicious coffee and tea, and restaurant all at your doorstep! I will definitely choose this accommodation again when in Chicago!!!!
Flat in South Loop
4.69 out of 5 average rating, 132 reviews

Cozy 1BR in South Loop | Convenience in the City

DavidRating, 5 stars2 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.
Top guest favourite
Flat in Jefferson Park
5 out of 5 average rating, 11 reviews

Extended Stay Large Studio:New Stylish, Affordable

DarrielRating, 5 stars6 days ago
This place is a 5 star in various areas. The place is spacious, new, clean and safe. The host is great. They take great care of those who book with them. Sometimes it’s hard to find great hosts who treat you the way that they want to be treated. They are a perfect example. They pay attention to the details. My stay was enjoyable and will book again. This was my second stay.
Flat in Chicago Loop
4.82 out of 5 average rating, 245 reviews

Spectacular Corner 2BR Penthouse in the Loop | Roo

KevinRating, 5 stars2 weeks ago
Great space and location to stay. The host is very nice to provide a white noise maker and ear plugs as the subway line is right next to the building and the noise was moderate. My wife and I slept well regardless of the noise.
Flat in South Loop
4.73 out of 5 average rating, 133 reviews

Kasa | Studio Near Museum Campus | South Loop

TaraRating, 5 stars1 week ago
Had an amazing stay! The place was super clean and exactly as described. Great location—would definitely book again
Flat in Streeterville
4.69 out of 5 average rating, 268 reviews

Sonder Onterie | King Studio Apartment

DwayneRating, 5 stars2 weeks ago
I was impressed from the moment I walked in until the very end. Beautiful space, awesome view, very clean and organized, and had everything I needed to maintain a clean space. This would be a great place for an extended vacation with the laundry units and update fridge. Everything you need to cook is there and you can perfectly control heating. Who can be mad at complimentary coffee? My only issue was not being able to cast streaming from my phone to tv. A place like this would do well with a rooftop pool as well however I’m very picky about shared pools/hot tubs in hospitality so I’m not too mad.

Private apartment rentals

Superhost
Flat in West Town
5 out of 5 average rating, 4 reviews

Modern & Spacious Condo Minutes from the Loop

AlanRating, 5 stars6 days 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 Lincoln Park
4.94 out of 5 average rating, 49 reviews

Coach House in Historic Old Town Chicago

CollinRating, 5 stars1 week ago
Great place to stay, it very nice in side, great little get away, would do it again and book with him again. He was very responsive and really made sure the place was nice and comfortable for us before we checked in he quickly throw an ac unit in the window for us it was very nice for him to do. We will be booking again when we come back!
Guest favourite
Flat in West Town
4.88 out of 5 average rating, 91 reviews

Garden on Warren

AlyssaRating, 5 stars6 days ago
Location was incredible and had quick access to almost anything. Area was quiet and peaceful to stroll through. The space was very clean and comfortable. I’d absolutely stay here again!
Flat in West Loop
4.89 out of 5 average rating, 27 reviews

1 Bedroom unit in Heart of Downtown| Skyline view

KathleenRating, 5 stars1 month ago
Good things: Host always responded quickly, fabulous view, very sunny, gorgeous sunsets, comfortable place, easy walks to the riverwalk and Fulton market, grocery store very close. just a fun, active place to be! Challenges: a bad smell randomly came up from the kitchen sink and maintenance could not fix it, so we burned candles; no a/c available bc it gets turned on (switched over from heat) when the whole building switches it which made it quite warm some days in April; only had one key for the two of us which made it hard to split up and do different things; saw 1 cockroach, but pest control took care of it immediately and there were never anymore, and we stayed there 1 month!...just being honest here because some of the 5 star reviews are not completely honest. We would stay here again, despite the challenges!
Guest favourite
Flat in Magnificent Mile
4.94 out of 5 average rating, 253 reviews

Urban Chic Apartment by the Magnificent Mile

ChristinaRating, 5 stars1 week ago
One of our best Airbnb experiences! Fabulous location and lovely apartment. A perfect home away from home for a week in the city. We really appreciated the extra touches like breakfast items and toiletries. Would love to come back on future visits to Chicago!
Guest favourite
Flat in River West
5 out of 5 average rating, 9 reviews

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

ViyadaRating, 5 stars4 days 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.
Top guest favourite
Flat in Belmont Gardens
4.99 out of 5 average rating, 95 reviews

Plants and Art | Near Trendy Restaurants & Bars

JosephRating, 5 stars1 week ago
My family and I had a great 3-night stay at Lynette and Efrain’s place. As others have said, the photos don’t quite do it justice. Pristinely clean, great layout, comfy beds, cool plants and art, and a kind & responsive host. Highly recommended and will stay again when in Chicago.
Top guest favourite
Flat in West Town
4.98 out of 5 average rating, 105 reviews

Cozy Studio in Perfect Location

AmoryRating, 5 stars1 week ago
This is a really nice spot. Had everything we needed. Lot of small shops and restaurants nearby. If you like to walk (which we do), downtown Chicago is only a couple miles away. It’s also not too expensive to uber there either. Had a great time!

Apartment rentals with a hot tub

Superhost
Flat in Humboldt Park
4.98 out of 5 average rating, 102 reviews

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

JessicaRating, 5 stars2 weeks ago
Thank you so much, Matthew! The beds were comfortable, the BNB was extremely clean, but still felt the coziness of Home. The hot tub definitely was the highlight of our wind down at night. We will be booking again!
Superhost
Flat in Chicago
4.84 out of 5 average rating, 76 reviews

Spacious Beautiful Condo

KristinRating, 5 stars1 week ago
Perfect location for a family to stay that’s close to everything. We did days in the city and a game at Wrigley. Very clean and perfect for our long weekend in Chicago.
Superhost
Flat in South Loop
4.67 out of 5 average rating, 309 reviews

Sentral Premium 2BR Apt South Loop Chicago

YvetteRating, 5 stars2 weeks ago
It was a great place to stay definitely felt like home! I went for the weekend and the restaurants around there were great. They communicated very well when I had questions and responded with good time. Thank you and I’ll see you next year! :)
Superhost
Flat in Bridgeport
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!!
Superhost
Flat in West Loop
4.96 out of 5 average rating, 25 reviews

Skyline Oasis: City & Lake Views

NatashaRating, 5 stars3 months ago
Let me just say, the pictures don’t do this cute, cozy place justice! I’m big on hospitality and customer service, and Johana and Akos were beyond accommodating and communicative. I would dare to say this is the most accommodating place I’ve experienced so far! The space has such a good energy and flow to it — cozy, inviting, and with a beautiful sunset view from the kitchen window that you can enjoy right from the living room sofa. The views are stunning, and the building itself is upscale, clean, and even smells great! I enjoy playing some of the games that were pervaded( Uno and Jenga) and I appreciated that the TVs had all the apps, HBO, Disney, prime, Netflix etc. It’s in a great location, and I felt very safe throughout my stay. The only con would be some city noise, but it didn’t bother me at all. There’s a nearby train that doesn’t pass often, and again, it wasn’t an issue for me. I would definitely recommend this place!!
Superhost
Flat in South Side
4.87 out of 5 average rating, 15 reviews

Large Studio Apartment with no cleaning fee

ErikaRating, 5 stars2 weeks ago
We had a good stay and David communicated very well with help that was needed. Good place to stay with anyone traveling with a small child. Thank you!
Superhost
Flat in River West
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars2 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 Near North Side
4.92 out of 5 average rating, 37 reviews

Lincoln Park Haven: Balcony, Walk to Whole Foods

HoustonRating, 5 stars1 month ago
We had a great stay at this apartment in Lincoln Park. The view was excellent, and the building amenities were a nice bonus. The location was convenient too--Whole Foods was right across the street, with other shops like REI nearby. It was easy to get downtown and explore other parts of Lincoln Park. We were traveling with a toddler and a newborn, and the host helped by providing a pack 'n play. Communication was clear and timely. Overall, a smooth experience.

Quick stats about flat rentals in Chicago Loop

  • Total rentals

    690 properties

  • Nightly prices starting at

    ₹856 before taxes and fees

  • Total number of reviews

    14K reviews

  • Family-friendly rentals

    210 properties are a good fit for families

  • Pet-friendly rentals

    410 properties allow pets

  • Rentals with a pool

    410 properties have a pool

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