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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Southwest Side Cottages

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Recommended hotels in Southwest Side

Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2087)
"Great place to stay!"
The price is CA $226
CA $305 total
includes taxes & fees
Sep 1 - Sep 2
Sable at Navy Pier Chicago, Curio Collection by Hilton
Claridge House
Cocktail bar

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1323)
"Great stay highly recommend!! "
The price is CA $115
CA $175 total
includes taxes & fees
Aug 25 - Aug 26
Claridge House
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2233)
"Great stay "
The price is CA $146
CA $195 total
includes taxes & fees
Sep 2 - Sep 3
Freehand Chicago
Rainbow Motel
Interior detail

Rainbow Motel

2.5 star property
5.0 out of 10, (10)
"It was a good stay the rooms are small tho but if you are going to have fun and just have somewhere to sleep then it’s perfect for a couple people "
The price is CA $121
CA $143 total
includes taxes & fees
Aug 26 - Aug 27
Rainbow Motel
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Fridge, microwave, oven, stovetop

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

9.0 out of 10, Wonderful, (18)
"It was great for our needs! Definitely hear EVERYTHING though as usual for most older places in the city."
The price is CA $97
CA $296 total
includes taxes & fees
Aug 25 - Aug 26
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Fridge, microwave, oven, stovetop

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

9.6 out of 10, Exceptional, (4)
"It was great it had the basic amenities for a family to enjoy the stay"
The price is CA $115
CA $381 total
includes taxes & fees
Aug 27 - Aug 28
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Dalia Flat - Sleeps 10 - 10 minutes to Downtown
Dining

Dalia Flat - Sleeps 10 - 10 minutes to Downtown

9.4 out of 10, Exceptional, (14)
"Nice amenities, and centrally located, grocery store near, nice full kitchen, nothing we didn’t like about."
The price is CA $118
CA $393 total
includes taxes & fees
Aug 26 - Aug 27
Dalia Flat - Sleeps 10 - 10 minutes to Downtown
Carlton Inn Midway
Coffee and/or coffee maker

Carlton Inn Midway

2.0 star property
6.4 out of 10, (1002)
"Staff are very friendly:) "
The price is CA $145
CA $170 total
includes taxes & fees
Aug 24 - Aug 25
Carlton Inn Midway
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Interior

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

The price is CA $111
CA $375 total
includes taxes & fees
Aug 26 - Aug 27
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Skylark Motel
Exterior

Skylark Motel

2.0 star property
4.6 out of 10, (114)
"A dump. Next time im forced to choose this place or a floor in the airport, I'll choose the floor."
The price is CA $151
CA $177 total
includes taxes & fees
Aug 24 - Aug 25
Skylark Motel
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1688)
"Very nice hotel. "
The price is CA $124
CA $154 total
includes taxes & fees
Aug 24 - Aug 25
Hotel Saint Clair- Magnificent Mile
Ohio House Motel
Reception

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Great place to stay!"
The price is CA $156
CA $183 total
includes taxes & fees
Aug 25 - Aug 26
Ohio House Motel
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2594)
"Great hotel! "
The price is CA $135
CA $159 total
includes taxes & fees
Sep 2 - Sep 3
Best Western Grant Park Hotel
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8985)
"Family had a great stay. "
The price is CA $149
CA $175 total
includes taxes & fees
Aug 24 - Aug 25
Congress Plaza Hotel
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1032)
"Great location "
The price is CA $169
CA $199 total
includes taxes & fees
Aug 24 - Aug 25
Best Western River North Hotel
Holiday Inn Express Chicago - Magnificent Mile by IHG
Exterior

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very good, (1008)
"Great hotel! "
The price is CA $192
CA $226 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Chicago - Magnificent Mile by IHG
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very good, (203)
"Great place "
The price is CA $129
CA $151 total
includes taxes & fees
Sep 1 - Sep 2
FOUND Hotel Chicago River North
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Exterior

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4.0 star property
9.6 out of 10, Exceptional, (1015)
"Great hotel To stay at :)"
The price is CA $242
CA $284 total
includes taxes & fees
Sep 22 - Sep 23
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
The Chicago Hotel Collection River North
Building design

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (567)
"It was a wonderful place to stay! "
The price is CA $164
CA $193 total
includes taxes & fees
Aug 24 - Aug 25
The Chicago Hotel Collection River North
Central Loop Hotel
Breakfast, lunch, dinner served; American cuisine

Central Loop Hotel

4.0 star property
8.6 out of 10, Excellent, (1812)
"Enjoyed our stay"
The price is CA $142
CA $167 total
includes taxes & fees
Sep 14 - Sep 15
Central Loop Hotel
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

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Property very nice, staff are very pleasant. Check in quick and easy."
Elaine 1-night trip
Posted 9 hours ago
InterContinental Chicago Magnificent Mile by IHG