Southwest Side Hotels

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Top 10 trending Southwest Side hotels

Carlton Inn Midway

2.0 star property
6.4 out of 10, (1008)
"Staff are very friendly:) "
The price is €105
includes taxes & fees
20 Aug - 21 Aug
Carlton Inn Midway

Rainbow Motel

2.5 star property
5.0 out of 10, (9)
"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 €90
includes taxes & fees
20 Aug - 21 Aug
Rainbow Motel

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 €109
includes taxes & fees
20 Aug - 21 Aug
Skylark Motel

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4544)
"Great stay and great location"
The price is €110
includes taxes & fees
2 Sept - 3 Sept
River Hotel

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2003)
"Pool area and deck were great for the family, beds were comfortable, location is great."
The price is €160
includes taxes & fees
26 Aug - 27 Aug
DoubleTree by Hilton Chicago - Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3081)
"Great stay!"
The price is €145
includes taxes & fees
24 Aug - 25 Aug
Eurostars Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very good, (3731)
"Our stay was wonderful."
The price is €153
includes taxes & fees
25 Aug - 26 Aug
Hilton Garden Inn Chicago Downtown/Magnificent Mile

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3602)
"Great hotel"
The price is €144
includes taxes & fees
24 Aug - 25 Aug
citizenM Chicago Downtown

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8994)
"lovely hotel, room was clean with comfy bed and great facilities. would definitely stay here again "
The price is €189
includes taxes & fees
14 Sept - 15 Sept
Congress Plaza Hotel

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 €189
includes taxes & fees
1 Sept - 2 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2221)
"Great stay "
The price is €121
includes taxes & fees
2 Sept - 3 Sept
Freehand Chicago

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2807)
"Clean, helpful staff and in walking distance to most places we visited."
The price is €140
includes taxes & fees
24 Aug - 25 Aug
Aloft Chicago Mag Mile

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2097)
"Awesome hotel, highly recommended."
The price is €166
includes taxes & fees
2 Sept - 3 Sept
Hilton Chicago

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1031)
"Great location "
The price is €127
includes taxes & fees
24 Aug - 25 Aug
Best Western River North Hotel

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
8.4 out of 10, Very good, (1015)
"Friendly staff and close to the places I wanted to go to "
The price is €163
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn & Suites Chicago - Downtown by IHG

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very good, (191)
"Great place "
The price is €98
includes taxes & fees
2 Sept - 3 Sept
FOUND Hotel Chicago River North

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1873)
"Helpful staff, beautiful hotel in a great location!"
The price is €196
includes taxes & fees
2 Sept - 3 Sept
Palmer House a Hilton Hotel

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2488)
"Had a wonderful stay here and staff was super friendly!"
The price is €150
includes taxes & fees
1 Sept - 2 Sept
La Quinta Inn & Suites by Wyndham Chicago Downtown

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2314)
"Beautiful hotel , breakfast was amazing "
The price is €176
includes taxes & fees
2 Sept - 3 Sept
Hotel Riu Plaza Chicago

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very good, (1011)
"Great stay"
The price is €144
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Express Chicago - Magnificent Mile by IHG
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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Explore attractions like Balzekas Museum of Lithuanian Culture and S.S. Peter and Paul Church as you discover things to see and do in Southwest Side.

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Top Southwest Side Hotel Reviews