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Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Chicago Vacation Homes

Clarendon Hills Top Floor
Fridge, microwave, oven, stovetop

Clarendon Hills Top Floor

7.2 out of 10, Good, (7)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor
Lincoln Park Living - Suite 2!
Fridge, microwave, oven, stovetop

Lincoln Park Living - Suite 2!

9.4 out of 10, Exceptional, (39)
"Great Place. Super area!"
Lincoln Park Living - Suite 2!
Great 3 bedroom rental unit near Logan Square
Fridge, microwave, oven, stovetop

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (49)
"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "
Great 3 bedroom rental unit near Logan Square
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Microwave, oven, stovetop, dishwasher

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

8.0 out of 10, Very good, (2)
"Very nice place "
The price is CA $205
CA $315 total
includes taxes & fees
Aug 12 - Aug 13
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

10.0 out of 10, Exceptional, (4)
"Great place"
The price is CA $216
CA $864 total
includes taxes & fees
Aug 20 - Aug 21
4BR Retreat w/ Theater, Game Room & Backyard
Cheerful 4 bedroom smart home w/ indoor fireplace
Fridge, microwave, oven, stovetop

Cheerful 4 bedroom smart home w/ indoor fireplace

8.0 out of 10, Very good, (14)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace
Cozy 3-bedroom house in family-oriented Melrose Park.
Property grounds

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

10.0 out of 10, Exceptional, (19)
"The home was clean and Maggie was very responsive in our chat when I needed something. Very lovely. "
Cozy 3-bedroom house in family-oriented Melrose Park.
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
Fridge, microwave, oven, stovetop

SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE

10.0 out of 10, Exceptional, (88)
"Easy to get to and very clean. Also check in and out was easy as well. "
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square
Terrace/patio

Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square

10.0 out of 10, Exceptional, (13)
"Lots of good food and close to transit! Amazing little spot."
Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Fridge, microwave, oven, stovetop

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

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Luxury Home Away From Your Home
Fridge, microwave, oven, stovetop

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (124)
"Property manager was very responsive and the communication was clear and helpful. The house was very clean. Although the neighborhood was very concerning, dirty with a lot of people standing on the block, no one was threatening and nothing happened during our stay. Parking on street was safe. "
Luxury Home Away From Your Home
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Smart TV, stereo

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (31)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Master qtr close to nature & easy urban facilities
Exterior detail

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (58)
"Great spot."
The price is CA $160
CA $280 total
includes taxes & fees
Aug 7 - Aug 8
Master qtr close to nature & easy urban facilities
Lincoln Park Living - Suite 1
Fridge, microwave, oven, stovetop

Lincoln Park Living - Suite 1

9.6 out of 10, Exceptional, (29)
"Ideal location and plenty of beds. Communication was easy. My friends and I kept saying how lucky we were to find this place. Highly recommend! "
Lincoln Park Living - Suite 1
Urban Farmhouse near O’Hare Airport
Exterior

Urban Farmhouse near O’Hare Airport

9.4 out of 10, Exceptional, (44)
"We enjoyed this old house! It was clean & furnished well. Owner very accessible & easy to work with. Would definitely stay here again!"
Urban Farmhouse near O’Hare Airport
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
Fridge, microwave, oven, stovetop

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

4.0 star property
9.4 out of 10, Exceptional, (40)
"The large number of bedrooms provides privacy for a lot of people."
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
Quaint Bungalow, near Great Lakes Naval Base
Dining

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (61)
"Great experience, lots of cooking materials "
The price is CA $186
CA $427 total
includes taxes & fees
Aug 10 - Aug 11
Quaint Bungalow, near Great Lakes Naval Base
South Shore Retreat 5 bedrooms/entertainment
Fridge, microwave, oven, stovetop

South Shore Retreat 5 bedrooms/entertainment

8.0 out of 10, Very good, (3)
"Three weeks later tries to say we didn't pay when we have emails/proof saying otherwise. We checked in at the time, and some guy just comes in the backdoor with towels. Upon checkout, says we didn't leave the key & they had to get a locksmith - we literally saw someone come in with a key (man with towels at check in). Scary neighborhood, misleading advertising, terrible communication. "
South Shore Retreat 5 bedrooms/entertainment
Cheerful 3 bedroom. Feels like home.
Fridge, microwave, oven, stovetop

Cheerful 3 bedroom. Feels like home.

3.5 star property
10.0 out of 10, Exceptional, (9)
"It’s a beautiful home, it had everything we needed. It was nice and comfortable!!! Me and my family enjoyed our stay!!!"
Cheerful 3 bedroom. Feels like home.
Stylish 3bd w/ backyard patio mins from Downtown!
Fridge, microwave, oven, stovetop

Stylish 3bd w/ backyard patio mins from Downtown!

2.0 star property
9.2 out of 10, Wonderful, (5)
"Very comfortable home. Location was great. Owners were very responsive and helpful. A storm on our last day unfortunately left us without power, owner was great at keeping us informed of status. Already went to book for our next trip but someone beat us to it. "
Stylish 3bd w/ backyard patio mins from Downtown!
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 Chicago Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"A most enjoyable stay at this hotel"
Suzanne 2-night trip
Posted 11 hours ago
Hyatt Regency Chicago