Apartment vacation rentals in Downtown Chicago

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Popular amenities for Downtown Chicago apartment rentals

Weekly apartment rentals

Guest favorite
A modern kitchen features sleek dark cabinetry and a spacious island with high-backed blue chairs. Stainless steel appliances are visible, alongside a decorative arrangement of plants. The open layout allows natural light to illuminate the area, enhancing the overall ambiance.
Apartment in Chicago
4.91 out of 5 average rating, 45 reviews

Condo Near Downtown Chicago

SaeedRating, 5 stars2 weeks ago
This air bnb was very nice! It made you want to spend time in it. Location was 10 min Uber or 20 min train into town.
Apartment in Chicago
4.77 out of 5 average rating, 176 reviews

Chic Corner 2BR in Streeterville | Roof Deck | Lak

ElanaRating, 5 stars1 week ago
Location was perfect! Will definitely stay there again! Host was super helpful and accommodating!!
Guest favorite
A spacious living area features a large sectional sofa set around a modern coffee table with a textured surface. Natural light floods in through large windows, illuminating a neutral color palette. Decorative plants and stylish furniture pieces enhance the contemporary design.
Apartment in Chicago
4.88 out of 5 average rating, 56 reviews

Downtown Penthouse Lake Views #1|Gym, Parking+Pool

AndriiRating, 5 stars3 weeks ago
We had a fantastic stay at this beautiful stay in downtown Chicago. The views were absolutely incredible! The home gave us a breathtaking look at the city skyline, day and night. The location couldn’t have been better, as it was right in the middle of everything, with restaurants, shops, and attractions all within pretty good walking distance. The unit itself was spotless when we arrived and had everything we needed. The bed was super comfortable, and the space felt both modern and welcoming. It was the perfect spot to relax after a day out exploring the city. The host was also very responsive and helpful!! Would definitely recommend this place to anyone looking for a clean, comfortable, and stylish stay in downtown Chicago. We’d happily stay here again!
Guest favorite
A cozy living area showcases orange sofas arranged around a dark wooden coffee table. Large windows with blinds offer natural light, while a vibrant mural of a city skyline adds visual interest. A ceiling fan provides circulation, enhancing comfort in the space.
Apartment in Chicago
4.84 out of 5 average rating, 43 reviews

Dwntown Mins Away/Relax & Stay! Bus/Train Friendly

JadeRating, 5 stars5 days ago
It was amazing , came for my 21 st ! It was clean and cute for a weekend trip ! Comfy bed and couch , the host always answered and checked up on us
A spacious bedroom features a large bed dressed in crisp white linens. Two bedside lamps provide soft illumination on either side. An abstract piece of wall art adds a modern touch, while natural light enters through the window, enhancing the clean lines of the room.
Apartment in Chicago
4.72 out of 5 average rating, 325 reviews

Sonder Market Hall | King Studio Apartment

Fernando & SanneRating, 5 stars1 month ago
great place to stay, really nice comfortable bed and full equipped kitchen
Superhost
A modern living area features exposed brick walls and large windows allowing ample natural light. A dark sofa is complemented by decorative pillows in teal, while a wooden coffee table occupies the center. A stylish bookshelf holds decorative items and a work desk is positioned nearby.
Apartment 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!
The exterior of a modern high-rise building is visible, featuring large glass windows and a curved architectural design. Surrounding trees line the street, creating a blend of urban and natural elements. The image showcases the building's height against a clear blue sky.
Apartment in Chicago
4.8 out of 5 average rating, 300 reviews

Kasa | Studio, Walk to Grant Park | South Loop

AlekseiRating, 5 stars4 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.
Guest favorite
A bright living area features large windows allowing natural light to fill the space. A light brown leather sofa and a cozy armchair are accompanied by a wooden coffee table. A decorative rug adds warmth, while shelves with potted plants and books enhance the inviting atmosphere.
Apartment 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!!

Private apartment rentals

Guest favorite
A spacious living area features a gray sectional sofa arranged around a wooden coffee table. Soft lighting is provided by ceiling fixtures and wall-mounted sconces. The room leads to a set of stairs, while a TV is mounted on the wall for entertainment.
Apartment in Forest Park
4.87 out of 5 average rating, 119 reviews

City-Accessible Basement Retreat

AmyRating, 5 stars2 weeks ago
Christopher’s place was perfect for our needs! The place was very roomy, the kitchen and bathroom was spotless and spacious, and the bed was comfortable. The neighborhood was quiet and calm with more than enough easy and free parking. The metro was less than a 10 minute walk which was perfect for us getting in and out of the city easily. They also allowed us to drop off our luggage before check in hours which we greatly appreciated. Needless to say, we enjoyed our stay and would strongly recommend staying here.
A spacious living area features high ceilings with a skylight and large windows, offering ample natural light. A comfortable green sofa and a black armchair are positioned near a coffee table. A fireplace and a television are visible, with scenic views seen through the glass doors.
Apartment in Chicago
5 out of 5 average rating, 3 reviews

Sunny Penthouse - Oakwood Beach

DeannaRating, 5 stars3 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 favorite
A spacious bedroom is highlighted by a large bed with soft blue and white linens. Natural light filters through two small windows adorned with navy curtains. A compact desk and bright yellow chair add a pop of color, complemented by abstract wall art.
Apartment 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.
A living area features a brown leather sofa with decorative cushions, complemented by a light-colored armchair. A wooden coffee table rests on a green area rug. A television is positioned nearby, with natural light entering through expansive windows.
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.
Guest favorite
A studio space features a spacious bed with a patterned blanket, complemented by a decorative mirror above the headboard. A small seating area with a chair and woven basket is situated beside a window adorned with privacy blinds. The floor is covered with a textured area rug.
Apartment in Chicago
4.89 out of 5 average rating, 450 reviews

Great Location Studio in the Gold Coast!!

KathrynRating, 5 stars1 week ago
This place was perfect for our stay. It is in a great location with a lot to do nearby. Although the building is older, the unit itself is extremely nice and spacious. It was very clean and Ensavi was so kind and responsive. This is such a steal compared to the prices of hotels nearby. Highly recommend!
Guest favorite
An open living area features a modern kitchen with stainless steel appliances and granite countertops. A dining table with seating for four is positioned next to a cozy seating area, which includes a large sofa and wall-mounted TV. Natural light filters through the windows.
Apartment 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 favorite
The living and dining area is designed with high ceilings and an open layout. A sofa is paired with a modern armchair, while a wooden dining table is surrounded by stylish chairs. Large windows bring in natural light, highlighting warm wood floors and minimal decor.
Apartment in Chicago
4.94 out of 5 average rating, 254 reviews

Urban Chic Apartment by the Magnificent Mile

AndrewRating, 5 stars2 weeks ago
Perfect location near Michigan, the river and the lake. Lovely apartment with great light. Although its located directly above a bar, there were no issues with noise. Would definitely stay here again for future trips back to Chicago
Guest favorite
A bright living area features floor-to-ceiling windows showcasing a skyline view. The muted colors of the comfortable sofa and accent chairs create a calming ambiance. A small side table sits next to an armchair, illuminated by natural light.
Apartment in Chicago
5 out of 5 average rating, 9 reviews

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

ViyadaRating, 5 stars1 week 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.

Apartment rentals with a hot tub

Guest favorite
An elevated outdoor space features multiple levels, including an upper deck with railing. Lush greenery and carefully arranged seating areas create an inviting atmosphere. The exterior of the structure is painted in soft hues, and large windows allow for ample natural light.
Apartment 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
An open-concept living and dining area is showcased with a gray sectional sofa and a wooden coffee table. A modern ceiling fan hangs above, and natural light fills the space. A dining table with six chairs is positioned nearby, adjacent to a sleek kitchen.
Apartment in Chicago
4.85 out of 5 average rating, 78 reviews

Spacious Beautiful Condo

SophiaRating, 5 stars1 day 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
A private hot tub is set on a rooftop deck, featuring bubbling water and a city skyline backdrop. Plush seating with soft cushions is arranged nearby, creating a comfortable space for relaxation. The view includes various high-rise buildings against a colorful sky.
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!!
Guest favorite
A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.
Apartment 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 favorite
The living area features a light-filled open layout with floor-to-ceiling windows. A plush sectional sofa is complemented by two stylish lounge chairs. A low coffee table sits on a modern area rug, with a decorative plant adding a touch of greenery to the space.
Apartment 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
A living area features two sofas and a coffee table centered on a colorful area rug. Warm lighting emanates from two table lamps beside the sofas. Artwork adorns the wall, enhancing the cozy ambiance of the space.
Apartment in Chicago
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars6 days 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.
Guest favorite
A hot tub is positioned on a rooftop terrace, with views of the Chicago skyline in the background. The space is framed by glass railings, allowing for an unobstructed vista of the city. Soft light reflects off the water, creating a serene atmosphere.
Apartment in Chicago
4.92 out of 5 average rating, 38 reviews

Lincoln Park Haven: Balcony, Walk to Whole Foods

KristenRating, 5 stars3 days ago
Loved our stay at The Foundry! The unit was beautiful and comfortable and the views were incredible. We had everything we needed and communication from Cloud9 was clear. There are great places nearby to walk for coffee and food — including an amazing Whole Foods.
Superhost
An indoor pool area is framed by tall windows, allowing natural light to fill the space. Elegant seating arrangements are situated around the pool, complemented by lush vertical greenery hanging from above. Soft lighting creates a serene environment for relaxation.
Apartment 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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