Apartment holiday rentals in West Loop, Chicago

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Popular amenities for West Loop, Chicago apartment rentals

Weekly apartment rentals

Flat in West Loop
4.6 out of 5 average rating, 15 reviews

Modern 1BR in Prime West Loop Location

RossRating, 5 stars1 week ago
We had an incredible stay in Chicago’s West Loop last week! The place was spotlessly clean and perfectly located, just steps away from fantastic restaurants, bars, and the vibrant heart of the West Loop. The digital keypad on the door made getting in and out incredibly easy, and the building felt very safe. The host was exceptional—clear instructions, always reachable, and stayed in touch throughout our trip to ensure everything went smoothly. Highly recommend this spot for anyone visiting Chicago!
Superhost
Flat in Near South Side
4.78 out of 5 average rating, 144 reviews

McCormick Place Studio/parking/sleeps up to 4

KirstenRating, 5 stars6 days ago
Very responsive and helpful hosts. The place was exactly as described. Would definitely recommend!
Guest favourite
Flat in West Loop
4.88 out of 5 average rating, 8 reviews

1BR Captivating Apartment

EvanRating, 5 stars6 days ago
Geo never took longer than 20 minutes to respond when needed, and found workarounds when I was having difficulties with website not working. The place was lovely, and had more than enough space. Location was great, and I didn't struggle to find parking. Thanks again for hosting!
Flat in West Loop
4.8 out of 5 average rating, 320 reviews

Sophisticated River West 2 Bedroom - Near the L

KymRating, 5 stars2 weeks ago
This Airbnb was very clean and comfortable for our group. Check-in was very easy and straightforward, and Drew was very responsive.
Flat in West Loop
4.83 out of 5 average rating, 35 reviews

Level Junior Two Bedroom Suite | Fulton Market

AlannaRating, 5 stars3 weeks ago
Had such a great stay! Everything was very clean and all information given was thorough.
Guest favourite
Flat in Near North Side
4.87 out of 5 average rating, 47 reviews

50th Floor Mag Mile VIEWS, Balcony, Pool, Gym

JoseRating, 5 stars1 month ago
Beautiful view especially at sunset and night time. And great restaurants nearby.
Top guest favourite
Flat in Magnificent Mile
4.99 out of 5 average rating, 88 reviews

Chic 2BR Gem with Fireplace

NatalieRating, 5 stars3 weeks ago
Everything about this stay was incredible. We will definitely stay here again! The location can’t be beat - it’s walkable to so much. The apartment itself is perfect for relaxing in the evenings with the superb common area. We had zero complaints! (And we left some of our belongings and were contacted immediately by the staff to let us know!). The concierge was so helpful as well! One of the best Airbnb’s either of us have stayed in!
Superhost
Flat in West Loop
5 out of 5 average rating, 4 reviews

Million Dollar Views! Luxury Downtown Skyhouse!

AnyaRating, 5 stars1 month ago
Great location nice view amazing host

Private apartment rentals

Guest favourite
Flat in West Town
4.91 out of 5 average rating, 384 reviews

The Craftsman Gallery at OHC - No Cleaning Fee!

HonoraRating, 5 stars3 weeks ago
I had a great time staying here. Not only does it look exactly like the pictures, but it was even more spacious than it seems in photos. The cleanliness of the space was pristine and spotless. The location is great too; there’s a train station basically a few steps out the front door. There were plenty of amenities including kitchenware, laundry, and toiletries. Matthew was very helpful in giving detailed instructions for check in as well as tips for places to check out in Chicago and the surrounding neighborhood. He was responsive and timely when I had any questions regarding my stay. I will definitely be booking with Matthew again as he has a ton of other awesome listings and I thoroughly enjoyed my experience here!
Flat in West Loop
4.83 out of 5 average rating, 18 reviews

Sophisticated 3BR Suite - Modern, and Luxurious

TaylorRating, 5 stars4 days ago
Great place! Brett and team communicated so well!
Flat in The Loop
4.72 out of 5 average rating, 243 reviews

Kasa | 1BD, Walk to Grant Park | South Loop

DaniceRating, 5 stars3 days ago
Clean and comfortable apartment in a great location! We enjoyed using the gym and the coffee bar. We found the area to be quiet while also close to everything! We really enjoyed the neighborhood including close access to Target and several great nearby restaurants. Highly recommend!
Top guest favourite
Flat in West Town
5 out of 5 average rating, 28 reviews

Here on Huron—spacious classic Chicago 2flat

TobiasRating, 5 stars1 week ago
The apartment was exactly as described – maybe even better! Everything was very clean and tastefully furnished. The location is fantastic: super central yet quiet, with direct access to the Blue Line and several bus routes – perfect for exploring the city. Host Jon was incredibly friendly, helpful, and always easy to reach. I felt welcome right away. Communication before and during the stay was smooth and uncomplicated. I would definitely stay here again – a great choice for anyone looking for a clean, well-located, and comfortable place to stay!
Flat in West Loop
4.86 out of 5 average rating, 7 reviews

Sun-Drenched 1BR Apartment

MadisonRating, 5 stars1 week ago
My husband and I loved staying at Brad’s place for our honeymoon! It was such a great location. It is right by the train so I appreciate that earplugs were provided to sleep! I would definitely recommend figuring out parking before you get there. We tried to figure it out when we got there, the spot hero app wasn’t working, it was weird! But if you have parking figured out, it’s the best place to stay! We might make this a yearly stop for us!
Top guest favourite
Flat in Lincoln Park
5 out of 5 average rating, 263 reviews

Explore Lincoln Park from a Polished Apartment

KatieRating, 5 stars1 week ago
You can believe the hype of the great reviews. Beth’s place has everything I want in an Airbnb. The decorations were thoughtful, there’s coffee and a full kitchen and a great shower and so many windows - all with black out blinds for night. Plus, the area is fantastic. I went on great neighborhood runs and it’s a quick straight shot to the lake too. Plus, the bus downtown is on the corner and really easy to navigate. Oh! And she left cookies for me! Thank you thank you, Beth!
Top guest favourite
Flat in West Town
4.98 out of 5 average rating, 64 reviews

West Town 1-Bedroom Full Remodel

JessicaRating, 5 stars1 week ago
This spot was absolutely perfect for our trip! The blue line stop was an easy walk away, there were plenty of restaurants and coffee shops less than 5 minutes away, and even a walkable grocery store with a pharmacy. Ubers/Lyfts are also super easy. The space was spotlessly clean from top to bottom, check-in was seamless, and the hosts left a lovely little guidebook with local recommendations and helpful tips.
Top guest favourite
Flat in Irving Park
4.98 out of 5 average rating, 61 reviews

Pine Beam Sloth Apartment next to Blue Line

CalebRating, 5 stars4 days ago
This place was great. Its location is extremely convenient for using public transit. Would highly recommend.

Apartment rentals with a hot tub

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

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

BriantRating, 5 stars1 week 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 West Rogers Park
4.84 out of 5 average rating, 77 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 Near South Side
5 out of 5 average rating, 34 reviews

Lux Loop Retreat: Amazing Views, Free Parking

JanRating, 5 stars1 day ago
Run, don't walk, to book this location for your Chicago stay. The view of the Chicago skyline is perfect, even better than if you stayed in Downtown itself, sometimes all you see is the wall of another building and no view. The instructions how to get there are very clear, if you're a little intimidated like I was about going to a big city never fear. The instructions are clear, easy to follow, and transit is close by to take you wherever you want to go. Overall great trip, thank you!
Superhost
Flat in Chicago
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars1 day 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.
Top guest favourite
Flat in West Town
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars3 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.
Guest favourite
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!!
Guest favourite
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.
Superhost
Flat in The Loop
4.69 out of 5 average rating, 48 reviews

Sentral 1 Bedroom Apt in South Loop Chicago

RichardRating, 5 stars6 days 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.

Quick stats about flat rentals in West Loop, Chicago

  • Total rentals

    360 properties

  • Nightly prices starting at

    $13 SGD before taxes and fees

  • Total number of reviews

    11K reviews

  • Family-friendly rentals

    150 properties are a good fit for families

  • Pet-friendly rentals

    210 properties allow pets

  • Rentals with a pool

    180 properties have a pool

Destinations to explore

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  4. Cook County
  5. Chicago
  6. West Loop
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