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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Southwest Side Vacation Homes

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

6.6 out of 10, (4)
"Very nice place "
The price is CA $204
CA $329 total
includes taxes & fees
Aug 19 - Aug 20
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.4 out of 10, Good, (8)
"Very communicative and good host for sure!"
The price is CA $179
CA $461 total
includes taxes & fees
Aug 19 - Aug 20
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
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, (51)
"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
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi
Fridge, microwave, oven, stovetop

Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi

8.0 out of 10, Very good, (3)
"Only complaint was the fact that the yard was not cut and the grass needed to maintained"
The price is CA $310
CA $626 total
includes taxes & fees
Sep 9 - Sep 10
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi
Cozy Home Sweet Homewood.
Fridge, microwave, oven, stovetop

Cozy Home Sweet Homewood.

9.6 out of 10, Exceptional, (32)
"Nice location outside of Chicago, cozy and clean, good communication, would definitely recommend! "
Cozy Home Sweet Homewood.
Vintage Urban Retreat
Exterior detail

Vintage Urban Retreat

10.0 out of 10, Exceptional, (9)
"Great house,great location,close to a lot of attractions and bars. Owners was egged to help and responded quickly to all our questions "
The price is CA $229
CA $695 total
includes taxes & fees
Aug 20 - Aug 21
Vintage Urban Retreat
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
8 bedrooms, desk, iron/ironing board, travel crib

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

2.0 out of 10, (1)
"When I booked this property it was the intention to have a joyful time with my family for an extended family event. We were unable to access the property the day of causing me to spend an extra 600 for us to stay at another hotel after spending 2 hours on the phone with customer service. To top it off we were harassed by the next door neighbor who attempted to take pictures of our vehicle and report to us that this property was considered an illegal listing. Once we gained entry the property was...
The price is CA $274
CA $1,331 total
includes taxes & fees
Aug 19 - Aug 20
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
Walk to the Beach! Theater-Coffee Bar-Games-Gym
Fridge, microwave, oven, stovetop

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.6 out of 10, Exceptional, (10)
"Everything was as it was described. Very nice "
Walk to the Beach! Theater-Coffee Bar-Games-Gym
LakeHouse
Fridge, microwave, oven, stovetop

LakeHouse

9.2 out of 10, Wonderful, (20)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse
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, (20)
"Comfortable beds and room for everyone. Nice quiet neighborhood and a great home away from home. Would stay there again. Host was very easy to work with and responded quickly to questions. "
Cozy 3-bedroom house in family-oriented Melrose Park.
Clarendon Hills Top Floor
Fridge, microwave, oven, stovetop

Clarendon Hills Top Floor

6.8 out of 10, (8)
"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
Cheerful 3 bedroom. Feels like home.
Fridge, microwave, oven, stovetop

Cheerful 3 bedroom. Feels like home.

3.5 star property
9.8 out of 10, Exceptional, (10)
"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.
Urban Farmhouse near O’Hare Airport
Exterior

Urban Farmhouse near O’Hare Airport

9.4 out of 10, Exceptional, (46)
"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
Home Sweet Home Spacious 4bed house with WiFi & Parking in fantastic Skokie
Fridge, microwave, oven, stovetop

Home Sweet Home Spacious 4bed house with WiFi & Parking in fantastic Skokie

8.0 out of 10, Very good, (4)
"The house was in a nice neighborhood and was very roomy and comfortable. Will be back."
Home Sweet Home Spacious 4bed house with WiFi & Parking in fantastic Skokie
New home w/view & party deck - 2nd Floor
Fridge, microwave, oven, stovetop

New home w/view & party deck - 2nd Floor

3.0 star property
10.0 out of 10, Exceptional, (22)
"Great location. Host was accessible and prompt to respond. "
New home w/view & party deck - 2nd Floor
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Fridge, microwave, oven, stovetop

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

8.6 out of 10, Excellent, (13)
"Great place, nice location and the Hosts are extremely good to work with. Highly recommend this just out of the city stay!"
The price is CA $318
CA $726 total
includes taxes & fees
Sep 8 - Sep 9
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

10.0 out of 10, Exceptional, (5)
The price is CA $137
CA $765 total
includes taxes & fees
Sep 2 - Sep 3
4BR Retreat w/ Theater, Game Room & Backyard
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Microwave, oven, stovetop, coffee/tea maker

13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

2.0 star property
8.4 out of 10, Very good, (5)
"Host was very nice and communicative! Kindly answered all my questions and made our stay amazing. Thanks! "
The price is CA $400
CA $909 total
includes taxes & fees
Aug 14 - Aug 15
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed
Lobby

Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed

9.0 out of 10, Wonderful, (2)
"It was nice and everyone was very friendly!!"
The price is CA $150
CA $197 total
includes taxes & fees
Aug 18 - Aug 19
Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed
Lincoln Park Living - Suite 1
Fridge, microwave, oven, stovetop

Lincoln Park Living - Suite 1

9.6 out of 10, Exceptional, (30)
"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
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 Southwest Side Hotel Reviews

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"Super fun place to stay in the heart of Chicago. The lights and shades are controlled by an IPad. One of the many features is the ability to change the color and intensity of the lights. There are also built in "mood" sound tracks to play to help you unwind, relax, or focus. The location couldn't be better, just steps from shopping, river strolling, and amazing restaurants. "
Laura 3-night trip
Posted 5 hours ago
citizenM Chicago Downtown