Apartment holiday rentals in Chicago River

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Popular amenities for Chicago River apartment rentals

Weekly apartment rentals

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

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

FriederikeRating, 5 stars3 weeks ago
Thank you so much. Looking forward to staying at your place again.
Apartment in Chicago
4.6 out of 5 average rating, 20 reviews

Modern 1BR in Prime West Loop Location

BrodieRating, 5 stars6 days ago
Great spot for a couple nights in the city. Is close to the L though so if you can’t sleep with noises at night that would be a drawback. Was fine for me though.
Apartment 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.
Superhost
Private room in Chicago
4.78 out of 5 average rating, 162 reviews

City Beat Room Amidst Chicago's Downtown Gems

AkiraRating, 5 stars1 month ago
Thank you very much Shammi. I was comfortable and at ease. I was very happy with my stay and I would like to thank you for your hospitality. It is right in front of the entrance to the Red Line Chicago subway station. If you have a big heavy bag, you should try your best to carry it up. However, the main entrance door to the building is self-locking, so you can safely lift them one by one.
Guest favourite
Private room in Chicago
4.91 out of 5 average rating, 210 reviews

ChicagoTreasure, Art Gallery w/Parking

IzabelRating, 5 stars4 days ago
Absolutely amazing all the way around! Beautiful place to stay in an amazing neighborhood! Colby was so incredibly helpful and kind, gave us a rundown of the neighborhood spots and the history. Bed was the most comfortable place I’ve slept in years! A 10/10
Apartment in Chicago
4.78 out of 5 average rating, 78 reviews

Studio w/ Large Terrace & Kitchenette, Lincoln Prk

RachelRating, 5 stars2 weeks ago
Absolutely loved staying here! Coffee on the deck, walking distance to the beach, Lincoln Park, restaurants, grocery stores and even downtown if youre up for a good walk. Ozlem responded to my questions immediately and even sent me a text or two to just check in and see how my stay was going. The place was clean and very comfortable. I would absolutely stay here again!!
Apartment in Chicago
4.77 out of 5 average rating, 142 reviews

Stylish 1BR South Loop Near McCormick & Wintrust

QuintonRating, 5 stars1 month ago
Great property. Host was very extremely responsive and helpful with any questions I had. I will definitely do business here again once I return to Chicago!
Guest favourite
Apartment in Chicago
5 out of 5 average rating, 14 reviews

Panoramic 2BR Penthouse in the Sky | Roof Deck

LukeRating, 5 stars3 days ago
very nice place, just like pictures. nice views of the lake. pool is a great bonus!

Private apartment rentals

Guest favourite
Apartment in Chicago
4.95 out of 5 average rating, 151 reviews

Cute, Clean, Cozy Apartment in Pilsen

AnnetteRating, 5 stars1 week ago
I was very impressed and pleased with all of the thoughtful details and extras like Keurig pods, filtered water and parking stickers. The space was cozy and perfect for our small family. It had every possible amenity needed to make ourselves at home for a week and cooking was a breeze. The location was ideal both due to the proximity to our daughter’s place, but also very quiet and walkable to everything you need including restaurants, stores, light rail and bus lines. Leigh-Anne was super responsive and flexible. The only word of caution would be that guests who are very tall (like over 6’) might find the ceilings too low, though they were perfect for us. We would definitely stay here again on a future trip.
Guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 243 reviews

Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D

TylerRating, 5 stars2 weeks ago
Clemente's place was in a great location central and walkable to many great areas and the train station, it was clean, it was easy to find, and it was comfortable. The beds were comfortable too, the A/C and heat was great, and the kitchen was well equipped. I would definitely recommend his place as a nicely affordable 2 bedroom in close proximity to the sites and restaurants.
Guest favourite
Apartment in Chicago
4.87 out of 5 average rating, 267 reviews

Spectacular Pilsen Studio for 2!

JillRating, 5 stars5 days ago
Nice area. 18th street has cool restaurants. Wish there was a grocery store close by. The place is super cute. Couch is a little hard. Hera was great with clear instructions. Would definitely stay again.
Guest favourite
Apartment in Chicago
4.89 out of 5 average rating, 244 reviews

1BR South Loop Loft I SuperHost + Top Rated!

EljinRating, 5 stars1 week ago
If it’s open. Book it! You won’t be disappointed. No matter where you’re going in Chicago or surrounding suburbs this location is a winner. Easy access to both CTA and Metra Union Station and the host are the best!
Guest favourite
Apartment in Chicago
4.92 out of 5 average rating, 384 reviews

Bright, Modern Apartment in a Vintage Greystone

MalloryRating, 5 stars1 week ago
Just returned from a stay at one of the most thoughtfully designed Airbnbs I’ve ever experienced. Every detail—from the curated artwork and cozy textures to the seamless layout and soft lighting—was intentionally chosen to create a sense of calm and comfort. It felt like the kind of space that anticipates your needs before you even realize them. A perfect blend of aesthetic beauty and livable design. Grateful for the warmth, care, and creativity that went into making it feel like home. The hosts were truly exceptional—kind, responsive, and incredibly thoughtful. From the moment I booked, they were proactive in ensuring everything was seamless, checking in with just the right balance of presence and privacy. Every message was warm and genuine, and it was clear they cared deeply about creating a welcoming experience. Their attention to detail went beyond the space itself; it extended into how they made me feel—completely at ease, valued, and cared for.
Superhost
Apartment in Chicago
4.86 out of 5 average rating, 407 reviews

Explore the City from an Elegant, Urban Retreat

YvonneRating, 5 stars2 weeks ago
Really enjoyed our stay! We found it easy to get everywhere we wanted. If you get a chance check out Move Along Coffee a few blocks away.
Guest favourite
Apartment in Chicago
4.95 out of 5 average rating, 128 reviews

BRAND NEW Elegant Renovation in Bucktown (Chicago)

CharlotteRating, 5 stars3 days ago
We absolutely loved our time in Dusanka’s flat, it was spotless clean, with everything you might need. The area is very lovely, lots of cafe and restaurants and very easy to get into the city, the airport and the lake.
Superhost
Apartment in Chicago
4.91 out of 5 average rating, 286 reviews

Gorgeous Penthouse with Stunning Views from Private Rooftop

SirtajRating, 5 stars2 weeks ago
Ross was a great host. There was a slight snafu at check in with the cleaners but Ross made an active and urgent effort to resolve the situation. Other than that, we had a great experience at this place. The master bedroom is lovely and the living room is full of light. The house is well equipped with everyone one could need. We had a great time at Ross’s place.

Apartment rentals with a hot tub

Guest favourite
Apartment in Chicago
4.98 out of 5 average rating, 104 reviews

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

AngeliqueRating, 5 stars2 weeks ago
It was a perfect place to stay for a few days. The skylights and all the beautiful plants really stood out. We really enjoyed the coffee bar to start our mornings. Lots of indoor and out door space. The room had the ability to adjust temperatures for each room. Great communication on check in etc.
Superhost
Apartment in Chicago
4.92 out of 5 average rating, 50 reviews

The Areal Oasis

Sheyla MRating, 5 stars2 weeks ago
I absolutely fell in love with this place! The amenities here alone will have you staying in for days because there is so much to do! The views are breathtaking and waking up to the view of the city will never get old! Everything you need is at a walkable distance and with the target right next door you will never be in need of a thing! Stephanie is a great host and very, very easy going. Will be coming back for sure!
Top Guest favourite
Apartment in Chicago
5 out of 5 average rating, 35 reviews

Lux Loop Retreat: Amazing Views, Free Parking

JanRating, 5 stars1 week 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
Apartment 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!!
Top Guest favourite
Apartment in Chicago
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars1 month 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
Apartment in Chicago
4.96 out of 5 average rating, 27 reviews

Skyline Oasis: City & Lake Views

NatalieRating, 5 stars3 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!
Superhost
Apartment 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
Apartment in Chicago
4.83 out of 5 average rating, 120 reviews

Penthouse Near Fulton: Skyline, Spacious

EmadRating, 5 stars4 days ago
Great place nice views , communication with host very smooth !

Destinations to explore