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Compare 900 Vacation Homes in Chicago with updated reviews, rates, and availability.

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (27)
"We were pleased with our stay. It met our needs. The only issue we had was the hot water in the bathtub/shower. It didn’t get hot, just tepid. The host had it checked out and said it was working. But we never got a hot shower. Parking was also an issue, but that’s the norm in Chicago. "
Great 3 bedroom rental unit near Logan Square

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

10.0 out of 10, Exceptional, (163)
"Great location, lots of space for gathering and hanging out. Tons of sleeping areas, air mattresses couches, futons, etc. Great for large groups of adults. Caution: Lots of stairs."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

9.6 out of 10, Exceptional, (16)
"Perfect location to make training visits to the area. Close to places to eat & grocery stores."
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

Updated Forest Park 3 BR Bungalow

10.0 out of 10, Exceptional, (100)
"The home is warm and inviting just like the pictures. Parking in the back of the house was easy. We cooked several times, pans, spices and dishes are available. The neighborhood is only about 20 minutes from downtown Chicago. The fenced in yard was perfect for our dog. We enjoyed our stay "
Updated Forest Park 3 BR Bungalow

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (5)
"We stayed on Valentine's weekend. Used the fireplace and the hot tub as these were must haves for us. Everything was very clean, so I felt a little bad dirtying the fireplace up. The owner was super responsive and accommodating. Would definitely consider staying again if we find ourselves in that area again."
Cozy 3-bedroom house in family-oriented Melrose Park.

LUXE 3 BR, 2 BA + Hot Tub

9.2 out of 10, Wonderful, (22)
"Hot tub was nice, the house itself was clean and had a great backyard that is big and pretty. Host is very responsive. Recommend!!"
The price is SAR 844
SAR 1,489 total
includes taxes & fees
25 Mar - 26 Mar
LUXE 3 BR, 2 BA + Hot Tub

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (87)
"Spacious property. Plenty of room and great neighborhood. Wish the larger TV was upstairs. "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (20)
"Perfect for what we needed "
Cozy Home Sweet Homewood.

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

9.6 out of 10, Exceptional, (8)
"The house is located in a neighborhood that is easily walkable and has anything you need within walking distance. Metro is located within a few blocks of the house and makes getting around easy."
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Charming ModernRetro Home!

9.2 out of 10, Wonderful, (13)
"Brittany was absolutely amazing. Her home was gorgeous and cozy. Served our needs exact. We will be coming back! "
Charming ModernRetro Home!

Private Home Awaits

The price is SAR 675
SAR 1,625 total
includes taxes & fees
23 Mar - 24 Mar
Private Home Awaits

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.4 out of 10, Exceptional, (10)
"House was clean and the check in process was easy. The gated driveway easily fit 3 cars with room to spare."
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

Riverfront Libertyville Retreat w/ Outdoor Kitchen

9.0 out of 10, Wonderful, (22)
"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Great place to stay in Warrenville

10.0 out of 10, Exceptional, (51)
"2nd stay with Kelly, everything was wonderful."
Great place to stay in Warrenville

The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!

9.8 out of 10, Exceptional, (73)
"We spent a wonderful long weekend enjoying the surrounding area. Plenty of shops, bars and restaurants within easy walking distance. The host was very good with communicating, unit was very spacious and clean. Perfect place to stay in Wrigleyville"
The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!

Chic and Spacious Bi-level 3BD in Bucktown!

2.0 star property
Chic and Spacious Bi-level 3BD in Bucktown!

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

10.0 out of 10, Exceptional, (4)
"Delightful home in charming neighborhood. The host was great to deal with, making sure we had what we needed for our toddler. All we had to bring was ourselves!"
Gorgeous historic mansion on UChicago campus. Renovation with original detail.

Luxury duplex home in Roscoe Village/Wrigley Field with Free Steet Parking

9.8 out of 10, Exceptional, (10)
"This was such a nice place in a great location. Really clean, comfortable, everything we needed. I would stay here again. Thank you!"
Luxury duplex home in Roscoe Village/Wrigley Field with Free Steet Parking

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (58)
"We drove up from Florida for our son’s Navy graduation. After 2 days on the road, the second day mostly in the freezing ice & snow, it was wonderful to come into this cozy, warm home. I loved the details & character of this older home. The floors squeak a little & there’s some clanging as the heater turns on, but I loved those little bits. It made it feel so much more like a home rather than a hotel. The location was perfect for travel to & from Naval Station Great Lakes. There are plenty of...
The price is SAR 506
SAR 1,133 total
includes taxes & fees
13 Apr - 14 Apr
Quaint Bungalow, near Great Lakes Naval Base
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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Other property types in Chicago

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (701)
"Friendly staff "
The price is SAR 507
SAR 705 total
includes taxes & fees
23 Mar - 24 Mar
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (451)
"Nice property, big clean rooms "
The price is SAR 350
SAR 411 total
includes taxes & fees
16 Apr - 17 Apr
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (266)
"Appartement spacieux, super fonctionnel, lit et divan lit très confortables. Très bien situé, à 2 min du metro dans un quartier hyper sécuritaire."
The price is SAR 400
SAR 470 total
includes taxes & fees
16 Apr - 17 Apr
Sonder Market Hall
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.