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Aug 15 - Aug 17
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Browse Select Hillside Condo Rentals

Experience Chicago living near United Center
Enjoy cooking in this well-equipped kitchen with a central island, white cabinetry, and granite countertop.

Experience Chicago living near United Center

9.0 out of 10, Wonderful, (16)
"Clean and cozy . Great communication . Not the best neighborhood but felt secure with passcode locks ! Would stay again "
Experience Chicago living near United Center
The Chic Urban Oasis Near the Lake!
Overlooking the sandy beach and rocky shoreline, this property offers stunning views of the surrounding lush greenery and distant buildings.

The Chic Urban Oasis Near the Lake!

8.0 out of 10, Very good, (7)
"Everything about the host and stay was amazing this will be my go to spot for my family and me"
The Chic Urban Oasis Near the Lake!
Modern Living 1BR in Warrenville
Classic Condo | Private kitchen

Modern Living 1BR in Warrenville

3.0 star property
8.4 out of 10, Very good, (6)
"My stay was short, but much better than a hotel."
Modern Living 1BR in Warrenville
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Enjoy cooking in this well-equipped kitchen with a central island, microwave, oven, refrigerator, sink, and dishwasher.

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.8 out of 10, Exceptional, (37)
"Fantastic! Great location, parking spot available, very clean! "
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Downtown Mich Ave #7| Park View Penthouse +gym
Relax on the outdoor terrace with a barbecue grill and comfortable seating.

Downtown Mich Ave #7| Park View Penthouse +gym

9.8 out of 10, Exceptional, (6)
"Great location...host quick response..."
Downtown Mich Ave #7| Park View Penthouse +gym
Urban Chicago Escape ~ 1 Mi to Local Beaches!
Kitchen features a microwave, gas stove, and oven, along with a granite countertop and stainless steel sink.

Urban Chicago Escape ~ 1 Mi to Local Beaches!

9.4 out of 10, Exceptional, (20)
"We met friends for the weekend. This was such a fun, comfortable place to stay. Plus it was a 5 minute walk to the train station, which made sight seeing in Chicago so accessible! We would definitely stay again!"
Urban Chicago Escape ~ 1 Mi to Local Beaches!
Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.
Relax in this stylish living room with a sofa, coffee table, and dining area, perfect for unwinding.

Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.

2.5 star property
10.0 out of 10, Exceptional, (1)
"The house was absolutely beautiful ! Very spacious and nice! Comfy beds and clean. "
Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.
Entire 2 bedroom with Office & Deck!
Enjoy panoramic views of the surrounding cityscape from this rooftop terrace.

Entire 2 bedroom with Office & Deck!

9.0 out of 10, Wonderful, (12)
"Good stay"
Entire 2 bedroom with Office & Deck!
Experience Chicago living near United Center
Enjoy cooking in this well-lit kitchen with a dishwasher, microwave, and oven.

Experience Chicago living near United Center

9.2 out of 10, Wonderful, (26)
"overall place is good, the only bad thing is the location!"
Experience Chicago living near United Center
Walking distance to restaurants, shops and Lake Michigan,
Classic corner building with a central entrance, surrounded by a black iron fence and lush greenery.

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (183)
"We enjoyed our stay in Rogers Park. The property was nice and a welcome retreat at the end of the day. "
Walking distance to restaurants, shops and Lake Michigan,
Elizabeth by Coast to Cactus | Chic Artists Loft
Enjoy a formal dining experience with a beautifully set table, complete with teapot and pitcher, in this stylish space.

Elizabeth by Coast to Cactus | Chic Artists Loft

9.2 out of 10, Wonderful, (20)
"Great place, excellent location and close to the trains!!!!"
Elizabeth by Coast to Cactus | Chic Artists Loft
NEW LUXURY CONDO WITH PATIO DECK
Relax on the covered patio with a wooden deck, wicker table, and chair.

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (173)
"This is the perfect place for you to stay when you’re in Chicago. We have stayed here at least four or five times already the place is immaculate. If you need any help someone is there for you ASAP. "
NEW LUXURY CONDO WITH PATIO DECK
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Classic residential building with a brick and stone facade, featuring a prominent entrance and large windows.

Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions

8.0 out of 10, Very good, (8)
"We enjoyed our stay, and the condo was perfect for my daughter and me. Great location, prompt responses to all communication with owner, super clean and very comfy beds! Main building corridor could use some sprucing up, but nothing major. Overall, very satisfied! Thanks, Khoy!"
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Walk to Train: Convenient Skokie Condo!
Enjoy cooking in this fully equipped kitchen with a dining area and convenient washing machine.

Walk to Train: Convenient Skokie Condo!

2.0 star property
10.0 out of 10, Exceptional, (2)
"The condo was spacious and situated in a nice area. Place is located nearby the yellow Skokie CTA line to take you into the city for activities. Host was helpful and quick to respond to any questions we had."
Walk to Train: Convenient Skokie Condo!
Wrigleyville Inn - Unit 1
Relax in this serene outdoor seating area with wicker furniture and a coffee table, surrounded by lush greenery and a brick backdrop.

Wrigleyville Inn - Unit 1

10.0 out of 10, Exceptional, (25)
"This home is beautiful, clean, and very well appointed. The location is great and in walking distance to so much. "
Wrigleyville Inn - Unit 1
Downtown MICH AVE#4 King Beds Grant Park, 2bd/2ba
Smart TV, books

Downtown MICH AVE#4 King Beds Grant Park, 2bd/2ba

9.4 out of 10, Exceptional, (26)
"Location was super close to everything downtown Chicago has to offer! Host was super responsive and was communicative the whole time"
Downtown MICH AVE#4 King Beds Grant Park, 2bd/2ba
Fun Dtown Penthouse #4 | Park, Museums +gym
Relax on the outdoor patio with a deck, table, and chairs, just steps from the interior living space.

Fun Dtown Penthouse #4 | Park, Museums +gym

9.6 out of 10, Exceptional, (11)
"It was a great location, space and host."
Fun Dtown Penthouse #4 | Park, Museums +gym
NEW LUXURY PENTHOUSE CONDO
Relax in a stylish seating area with a wicker sofa, armchair, and coffee table, surrounded by lush greenery and a brick wall.

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (185)
"A perfect place to stay. The rooftop bar has the BEST views of the city, especially around sunset. I would definitely stay here again! "
NEW LUXURY PENTHOUSE CONDO
Fun Downtown Penthouse #3 | Vintage +balcony&gym
Experience the unique wave-like roof structure and expansive glass facades of this contemporary building, perfect for events and gatherings.

Fun Downtown Penthouse #3 | Vintage +balcony&gym

9.6 out of 10, Exceptional, (13)
"The location is fantastic with the red L line popping out across the street. Small markets to get necessities nearby with plenty of restaurants. We had a family of four but it worked great for us. We had a few questions that came up and the management was very quick to respond. A"
Fun Downtown Penthouse #3 | Vintage +balcony&gym
Just remodeled apartment close to airport and mall
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator and ample counter space.

Just remodeled apartment close to airport and mall

10.0 out of 10, Exceptional, (11)
"The location was great for my purposes, nice apartment, great neighborhood and close to the airport."
The price is CA $186
CA $343 total
includes taxes & fees
Aug 9 - Aug 10
Just remodeled apartment close to airport and mall
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hillside Hotel Reviews

Freehand Chicago

Freehand Chicago

10/10 Excellent
"Front desk has a lot of patience and are really nice during the stay when u need anything! Day bartenders make great espresso martini’s! Taxi to airport at a flat fee was convenient."
James 2-night trip
Posted 13 hours ago
Freehand Chicago