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Aug 29 - Aug 31
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Sep 19 - Sep 21
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Oct 17 - Oct 19

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, (2092)
"Great place to stay!"
The price is CA $226
CA $306 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, (1311)
"He a great time, clean hotel"
The price is CA $125
CA $188 total
includes taxes & fees
Aug 24 - Aug 25
Claridge House
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2229)
"Great stay "
The price is CA $139
CA $188 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 $124
CA $146 total
includes taxes & fees
Aug 21 - Aug 22
Rainbow Motel
Dalia Flat - Sleeps 10 - 10 minutes to Downtown
Dining

Dalia Flat - Sleeps 10 - 10 minutes to Downtown

9.4 out of 10, Exceptional, (13)
"Nice amenities, and centrally located, grocery store near, nice full kitchen, nothing we didn’t like about."
The price is CA $118
CA $392 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, (1001)
"Staff are very friendly:) "
The price is CA $145
CA $170 total
includes taxes & fees
Aug 21 - Aug 22
Carlton Inn Midway
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 21 - Aug 22
Skylark Motel
Ohio House Motel
Reception

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1011)
"Great place to stay!"
The price is CA $151
CA $177 total
includes taxes & fees
Aug 25 - Aug 26
Ohio House Motel
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (9014)
"Very great location & helpful staff"
The price is CA $165
CA $194 total
includes taxes & fees
Aug 24 - Aug 25
Congress Plaza Hotel
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2584)
"Great hotel! "
The price is CA $136
CA $159 total
includes taxes & fees
Sep 2 - Sep 3
Best Western Grant Park Hotel
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1698)
"We loved the price and location of this hotel. "
The price is CA $151
CA $187 total
includes taxes & fees
Aug 24 - Aug 25
Hotel Saint Clair- Magnificent Mile
The Chicago Hotel Collection River North
Building design

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (561)
"It was a wonderful place to stay! "
The price is CA $177
CA $207 total
includes taxes & fees
Aug 24 - Aug 25
The Chicago Hotel Collection River North
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, (1001)
"Great stay"
The price is CA $200
CA $234 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, (193)
"Great place "
The price is CA $135
CA $159 total
includes taxes & fees
Sep 2 - Sep 3
FOUND Hotel Chicago River North
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3608)
"Great place"
The price is CA $199
CA $234 total
includes taxes & fees
Aug 24 - Aug 25
citizenM Chicago Downtown
Millennium Knickerbocker Chicago
Lobby lounge

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1943)
"Great stay"
The price is CA $189
CA $254 total
includes taxes & fees
Aug 26 - Aug 27
Millennium Knickerbocker Chicago
River Hotel
Lobby

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4538)
"Great place to stay, staff was very friendly"
The price is CA $152
CA $178 total
includes taxes & fees
Sep 3 - Sep 4
River Hotel
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1028)
"Great location "
The price is CA $176
CA $206 total
includes taxes & fees
Aug 24 - Aug 25
Best Western River North Hotel
Level Chicago Fulton Market
Executive lounge

Level Chicago Fulton Market

4.0 star property
9.2 out of 10, Wonderful, (272)
"Great place. Good stay for family vacation to Chicago"
The price is CA $219
CA $288 total
includes taxes & fees
Sep 3 - Sep 4
Level Chicago Fulton Market
Central Loop Hotel
Breakfast, lunch, dinner served; American cuisine

Central Loop Hotel

4.0 star property
8.6 out of 10, Excellent, (1808)
"Enjoyed our stay"
The price is CA $135
CA $159 total
includes taxes & fees
Sep 3 - Sep 4
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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

10/10 Excellent
"Great spot, good location, nice rooms. "
John 1-night trip
Posted 10 hours ago
Hotel Felix River North/Magnificent Mile