
Apartment vacation rentals in Downtown Chicago
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Top-rated apartment rentals in Downtown Chicago
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Popular amenities for Downtown Chicago apartment rentals
Weekly apartment rentals

Condo Near Downtown Chicago
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.

Chic Corner 2BR in Streeterville | Roof Deck | Lak
Location was perfect! Will definitely stay there again! Host was super helpful and accommodating!!

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

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

Sonder Market Hall | King Studio Apartment
great place to stay, really nice comfortable bed and full equipped kitchen

Modern & Spacious Condo Minutes from the Loop
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!

Kasa | Studio, Walk to Grant Park | South Loop
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.

Flor de Luna ~ Little Village Chicago Retreat
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

City-Accessible Basement Retreat
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.

Sunny Penthouse - Oakwood Beach
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!

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

Cozy 1BR in South Loop | Convenience in the City
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.

Great Location Studio in the Gold Coast!!
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!

Old Town Tranquility (+parking)
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!

Urban Chic Apartment by the Magnificent Mile
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

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

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

Spacious Beautiful Condo
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!

Rooftop HotTub As Seen On "Married At First Sight"
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!!

Skyline Oasis: City & Lake Views
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!

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop
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.

Large Studio Apartment with no cleaning fee
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.

Lincoln Park Haven: Balcony, Walk to Whole Foods
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.

Sentral 1 Bedroom Apt in South Loop Chicago
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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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club
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