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Aug 29 - Aug 31
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Oct 17 - Oct 19

Browse Select Southwest Side Vacation Homes

Cozy Room with Rooftop Lounge & City Views in River North
Property grounds

Cozy Room with Rooftop Lounge & City Views in River North

10.0 out of 10, Exceptional, (1)
"The hotel was very nice and the location was excellent. Was able to walk to many locations. Noise wasn't bad for a city experience. Hotel restaurant was very good."
The price is CA $215
CA $318 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Room with Rooftop Lounge & City Views in River North
The One: A 1BR Stay That Feels Like Home
Fridge, microwave, oven, stovetop

The One: A 1BR Stay That Feels Like Home

8.0 out of 10, Very good, (1)
"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."
The price is CA $144
CA $303 total
includes taxes & fees
Sep 2 - Sep 3
The One: A 1BR Stay That Feels Like Home
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is CA $148
CA $308 total
includes taxes & fees
Sep 2 - Sep 3
Stylish 1BR in West Loop
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop

Sun-Drenched 1BR Apartment

The price is CA $148
CA $308 total
includes taxes & fees
Sep 2 - Sep 3
Sun-Drenched 1BR Apartment
2 Connecting Suites at a 4⭐️ Hotel
Banquet hall

2 Connecting Suites at a 4⭐️ Hotel

The price is CA $757
CA $1,022 total
includes taxes & fees
Sep 1 - Sep 2
2 Connecting Suites at a 4⭐️ Hotel
2 Connecting Suites at a 5⭐️ Hotel
Exterior

2 Connecting Suites at a 5⭐️ Hotel

The price is CA $3,653
CA $4,930 total
includes taxes & fees
Sep 1 - Sep 2
2 Connecting Suites at a 5⭐️ Hotel
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Exterior detail

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
10.0 out of 10, Exceptional, (7)
"Very clean in a safe neighborhood. I would stay here again"
The price is CA $198
CA $276 total
includes taxes & fees
Aug 28 - Aug 29
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Cozy house in the city
Outdoor dining

Cozy house in the city

2.0 star property
8.8 out of 10, Excellent, (3)
"it was nice"
The price is CA $245
CA $551 total
includes taxes & fees
Aug 25 - Aug 26
Cozy house in the city
Getaway Near ORD With Great Local Amenities
Fridge, microwave, oven, stovetop

Getaway Near ORD With Great Local Amenities

8.8 out of 10, Excellent, (3)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
The price is CA $104
CA $397 total
includes taxes & fees
Aug 26 - Aug 27
Getaway Near ORD With Great Local Amenities
Chic Studio in Heart of Chicago
Fridge, oven, stovetop, coffee/tea maker

Chic Studio in Heart of Chicago

10.0 out of 10, Exceptional, (1)
The price is CA $123
CA $275 total
includes taxes & fees
Aug 25 - Aug 26
Chic Studio in Heart of Chicago
Spacious 3br home near Chicago, fenced yard for pets
Fridge, microwave, oven, stovetop

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
9.2 out of 10, Wonderful, (10)
"Nice property easy check in. Experience was amazing. Thank you again "
The price is CA $314
CA $628 total
includes taxes & fees
Sep 2 - Sep 3
Spacious 3br home near Chicago, fenced yard for pets
Comfy Studio in Portage Park- Great Value!
Iron/ironing board, travel crib, WiFi

Comfy Studio in Portage Park- Great Value!

The price is CA $123
CA $261 total
includes taxes & fees
Aug 26 - Aug 27
Comfy Studio in Portage Park- Great Value!
Luxury Unit with Rooftop Lounge & Spectacular City Views
Property grounds

Luxury Unit with Rooftop Lounge & Spectacular City Views

The price is CA $179
CA $277 total
includes taxes & fees
Aug 25 - Aug 26
Luxury Unit with Rooftop Lounge & Spectacular City Views
Enamored in Elmhurst
Smart TV

Enamored in Elmhurst

2.0 star property
10.0 out of 10, Exceptional, (12)
"Great stay"
The price is CA $294
CA $682 total
includes taxes & fees
Aug 25 - Aug 26
Enamored in Elmhurst
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)
"The property was very spacious and clean and customer service is very responsive and quick. "
The price is CA $185
CA $468 total
includes taxes & fees
Aug 25 - Aug 26
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Spacious Room with Rooftop Lounge & Scenic Views of Chicago
Property grounds

Spacious Room with Rooftop Lounge & Scenic Views of Chicago

The price is CA $227
CA $335 total
includes taxes & fees
Aug 25 - Aug 26
Spacious Room with Rooftop Lounge & Scenic Views of Chicago
Great Layout – Spacious 2BR Apt
Fridge, microwave, oven, stovetop

Great Layout – Spacious 2BR Apt

10.0 out of 10, Exceptional, (3)
"Clean, comfortable, and would definitely stay again!"
The price is CA $122
CA $294 total
includes taxes & fees
Sep 22 - Sep 23
Great Layout – Spacious 2BR Apt
Modern Suite with Rooftop Lounge & Views of Downtown Chicago
Property grounds

Modern Suite with Rooftop Lounge & Views of Downtown Chicago

The price is CA $262
CA $381 total
includes taxes & fees
Aug 25 - Aug 26
Modern Suite with Rooftop Lounge & Views of Downtown Chicago
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

7.8 out of 10, Good, (6)
"The house was immaculate and very spacious. Beautifully decorated. The neighborhood was easy to get in and out of and close enough to downtown. Would highly recommend."
The price is CA $205
CA $331 total
includes taxes & fees
Aug 25 - Aug 26
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Chic apartment with fitness room and AC in beautiful Chicago
Exterior

Chic apartment with fitness room and AC in beautiful Chicago

7.0 out of 10, Good, (2)
"This was a nice apartment and stay forThe price. Close to train station. However would be nice to add a microwave. I had to reach out by calling the host after no response about check in information on VRBO app. Received the check in information very late the night prior to my stay. Was charged 50 for early check in but when we arrived they were stillCleaning and we had to wait about 15-20minutes outside. Overall with all the inconveniences. It ended up being good stay for the price. "
The price is CA $76
CA $338 total
includes taxes & fees
Aug 26 - Aug 27
Chic apartment with fitness room and AC in beautiful 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.
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Top Southwest Side Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Great location, great hotel, friendly and helpful staff."
Scott 3-night trip
Posted 20 hours ago
The Royal Sonesta Chicago Downtown