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Compare 495 Vacation Homes in Chicago with updated reviews, rates, and availability.

Living Room / Dining Room
Lincoln Park Living - Suite 2!
10.0 out of 10, Exceptional, (2)
"Location can't be beat. 15 min drive to Lincoln Park Zoo though (which was our destination) -not 3 min We were so happy with the location and it had all that we needed stocked. Finding free parking was relativrly easy which is a great plus. But if you are looking for a quiet place, this is not for you. You have to sacrifice peace & quiet for the location"
Lincoln Park Living - Suite 2!
Luxury Downtown Penthouse with Private Rooftop!
10.0 out of 10, Exceptional, (4)
"Good host"
Luxury Downtown Penthouse with Private Rooftop!
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, (7)
"This property is huge for a city apartment. Our family of 5 (two parents, three kids) had plenty of space. The newly updated kitchen is very pretty. It is a short walk to many restaurants and Lincoln Park Zoo. The property manager was very responsive to my questions. We would definitely stay here again."
Beautiful, Remodeled Penthouse Unit in Old Town!
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Dining
Your Next Vacation Home
10.0 out of 10, Exceptional, (9)
"This home was very Beautiful and More Spacious than expected with a Beautiful back yard that we sadly didn’t get to enjoy because of the rain. The house location was great with A lot of stores and restaurants nearby. Next time we have a Family gathering I definitely will be rebooking"
The price is SAR 675
SAR 1,212 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Your Next Vacation Home
Breathtaking Downtown Penthouse B - Sleeps 11
10.0 out of 10, Exceptional, (2)
"We booked this property for a stay while I took 2 of my sons to the Twins game at Guaranteed Rate Field. Overall it was a great place to stay, it was close to the Field Museum and Lincoln Park Zoo that we went to, and was easy to get to and from the baseball park as well. I do hope they get the tv on the rooftop patio working though, we didn’t really use that space since the tv wasn’t working while we were there. That was the only real downfall of the trip!"
Breathtaking Downtown Penthouse B - Sleeps 11
Exterior
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
Breathtaking Downtown Penthouse A - Sleeps 11!
8.0 out of 10, Very Good, (1)
"Lots of stairs and they were slippery. Make sure you let your guest know to wear shoes when going up the stairs. Love the view at night on the top deck. Would have like a TV in the master bedroom. Other than that, we had a wonderful stay. Thanks."
Breathtaking Downtown Penthouse A - Sleeps 11!
Dining
LUXE 3 BR, 2 BA + Hot Tub
9.2 out of 10, Wonderful, (9)
"Our team had a one day conference in Chicago. Although it was near the highway it wasn't very loud. Decent neighborhood and the good part is that it was near the highway. Lower level bed is uncomfortable, no other way to say that. I still give it 5-stars as it is as advertised. Communication with owner was timely."
The price is SAR 563
SAR 955 total
includes taxes & fees
21 Jum. I - 22 Jum. I
LUXE 3 BR, 2 BA + Hot Tub
Living area
Relax & enjoy private house, green and quiet
Relax & enjoy private house, green and quiet
Living area
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (30)
"Great place for staying for visiting Wheaton. Very clean."
The price is SAR 638
SAR 1,095 total
includes taxes & fees
20 Jum. I - 21 Jum. I
✽ Charming Cottage ✽ close to College/Town/Station
Interior
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Welcome to our exquisite living room, where luxury meets comfort!
Game room/King Bed /Wi-Fi/Deck + Fire Pit
10.0 out of 10, Exceptional, (13)
"Relaxing, quiet and clean neighborhood. Love the retro decor. Kitchen is well equipped for those that might want to cook. A few branches were down in backyard, furniture wasn't set out yet such as outdoor dining table and chairs or gazebo, but overall property was in good condition. Thank you for a relaxing place to stay."
The price is SAR 770
SAR 1,596 total
includes taxes & fees
20 Jum. I - 21 Jum. I
Game room/King Bed /Wi-Fi/Deck + Fire Pit
Comfortable place to hang out
Free Parking! Designed for Work and Play - Perfect for Any Traveler with 2 Work Spaces and Old Town Charm by RedAwning
8.8 out of 10, Excellent, (28)
"Great property. Amazing location. And a dedicated parking spot!"
Free Parking! Designed for Work and Play - Perfect for Any Traveler with 2 Work Spaces and Old Town Charm by RedAwning
Living area
Freshly Remodeled Cozy Home
10.0 out of 10, Exceptional, (15)
"Place was clean and decor was nice and owner responed very nice to any questions."
Freshly Remodeled Cozy Home
Exterior
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
"Had a great time used space for birthday event!!"
The price is SAR 1,125
SAR 1,296 total
includes taxes & fees
20 Jum. I - 21 Jum. I
national historic home near downtown airports no parties no events
Open main level floor plan makes the space perfect for group & family gatherings
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (70)
"The house and location was perfect for our group trip to Chicago. Ample rooms and beds for everyone, and host was extremely responsive throughout the process and our stay. Walking distance to a bunch of great restaurants and bars. Would definitely stay again!"
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Private kitchen
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
9.0 out of 10, Wonderful, (43)
"We stayed at this property for a weekend family gathering in Chicago. This property had exactly the attributes we needed: separate spaces in which to sleep, a common space to gather, and a central location. It was a bit noisy, but nothing unexpected considering we were in Chicago on a weekend. Would recommend!"
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Living room: 
55” tv w/roku 
Air mattress 
Sectional
Chase
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, (8)
"The proximity to Great Lakes Recruitment Center, Sarge’s Meet & Greet, restaurants, etc. is perfect. We were in town for our son’s boot camp graduation and knew we wanted more room to hang out than a typical hotel room would offer. It was great to be able to relax, watch movies, just hang out with our sailor for the precious two days we had. This place has location, location, location if you’re coming in for boot camp graduation."
The price is SAR 454
SAR 881 total
includes taxes & fees
26 Jum. I - 27 Jum. I
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Private kitchen
Fully Updated home. Great for the entire family!
7.6 out of 10, Good, (10)
"My impression of the inside was good. However the outside needs some work. Maybe some up grades in the furniture would be beneficial. Other then that it was an enjoyable experience Thank u"
Fully Updated home. Great for the entire family!
Private kitchen
Cozy, King bed with heated bathroom!
9.8 out of 10, Exceptional, (8)
"Great"
Cozy, King bed with heated bathroom!
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See all available properties in Chicago
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.

Other property types in Chicago

Garden
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (404)
"Beautiful place to stay in Chicago. Love the area across from the park. Would definitely stay here again!"
The price is SAR 521
SAR 722 total
includes taxes & fees
27 Jum. I - 28 Jum. I
Sentral Michigan Avenue
Living area
Sonder Market Hall
3.5 star property
8.2 out of 10, Very Good, (80)
"Gorgeous rooms. Simple and quiet property. "
The price is SAR 344
SAR 397 total
includes taxes & fees
27 Jum. I - 28 Jum. I
Sonder Market Hall
Room
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (295)
"Overall the stay was amazing. We will definitely be booking here again."
The price is SAR 655
SAR 756 total
includes taxes & fees
10 Jum. II - 11 Jum. II
Sonder South Wabash
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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