
Find hotels in Southwest Side, IL from $64
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Our top choices for Southwest Side hotels

1. Holiday Inn Chicago – Midway Airport S by IHG
Holiday Inn Chicago – Midway Airport S by IHGWest Lawn
8.2 out of 10, Very Good, (1,007 reviews)
$141 nightly
The price is $164
Aug 9 - Aug 10
Total with taxes and fees

2. Carlton Inn Midway
Carlton Inn MidwayArcher Heights
6.2 out of 10, (1,004 reviews)
$102 nightly
The price is $120
Aug 30 - Aug 31
Total with taxes and fees

3. Skylark Motel
Skylark MotelGarfield Ridge
4.6 out of 10, (131 reviews)
$85 nightly
The price is $100
Aug 25 - Aug 26
Total with taxes and fees

4. Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by HiltonDowntown Chicago
9.4 out of 10, Exceptional, (2,629 reviews)
$230 nightly
The price is $273
Aug 31 - Sep 1
Total with taxes and fees

5. Congress Plaza Hotel
Congress Plaza HotelDowntown Chicago
8.0 out of 10, Very Good, (10,174 reviews)
$145 nightly
The price is $172
Aug 30 - Aug 31
Total with taxes and fees

6. Best Western Grant Park Hotel
Best Western Grant Park HotelDowntown Chicago
8.2 out of 10, Very Good, (2,753 reviews)
$143 nightly
The price is $170
Aug 30 - Aug 31
Total with taxes and fees

7. Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown ChicagoDowntown Chicago
7.6 out of 10, Good, (2,705 reviews)
$123 nightly
The price is $147
Aug 31 - Sep 1
Total with taxes and fees

8. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection HotelDowntown Chicago
9.6 out of 10, Exceptional, (1,293 reviews)
$167 nightly
The price is $199
Aug 30 - Aug 31
Total with taxes and fees

9. Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South LoopDowntown Chicago
8.8 out of 10, Excellent, (2,107 reviews)
$161 nightly
The price is $191
Aug 31 - Sep 1
Total with taxes and fees

10. Hilton Chicago
Hilton ChicagoDowntown Chicago
8.6 out of 10, Excellent, (3,005 reviews)
$219 nightly
The price is $261
Aug 30 - Aug 31
Total with taxes and fees

11. Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHGDowntown Chicago
8.6 out of 10, Excellent, (1,117 reviews)
$181 nightly
The price is $215
Aug 30 - Aug 31
Total with taxes and fees

12. Le Méridien Essex Chicago
Le Méridien Essex ChicagoDowntown Chicago
9.0 out of 10, Wonderful, (1,004 reviews)
$158 nightly
The price is $188
Aug 30 - Aug 31
Total with taxes and fees

13. The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastDowntown Chicago
8.0 out of 10, Very Good, (1,887 reviews)
$152 nightly
The price is $181
Aug 11 - Aug 12
Total with taxes and fees

14. Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownDowntown Chicago
9.2 out of 10, Wonderful, (2,330 reviews)
$199 nightly
The price is $236
Aug 25 - Aug 26
Total with taxes and fees

15. Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopDowntown Chicago
9.4 out of 10, Exceptional, (1,161 reviews)
$176 nightly
The price is $209
Aug 30 - Aug 31
Total with taxes and fees

16. DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileDowntown Chicago
8.8 out of 10, Excellent, (2,544 reviews)
$161 nightly
The price is $191
Aug 30 - Aug 31
Total with taxes and fees

18. LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonDowntown Chicago
9.4 out of 10, Exceptional, (3,799 reviews)
$242 nightly
The price is $288
Aug 23 - Aug 24
Total with taxes and fees

19. Claridge House Chicago, Tapestry Collection by Hilton
Claridge House Chicago, Tapestry Collection by HiltonDowntown Chicago
9.0 out of 10, Wonderful, (1,457 reviews)
$155 nightly
The price is $184
Aug 30 - Aug 31
Total with taxes and fees

20. Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesDowntown Chicago
9.0 out of 10, Wonderful, (4,701 reviews)
$161 nightly
The price is $191
Aug 30 - Aug 31
Total with taxes and fees
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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Stay near popular Southwest Side attractions
Learn more about Southwest Side
Explore attractions like Balzekas Museum of Lithuanian Culture and Ephraim Bajar Cultural Center as you discover things to see and do in Southwest Side.

Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport
Top Southwest Side Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast
10/10 Excellent
More cheap stays in Southwest Side

Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
$57 nightly
The price is $64 total per night from Aug 24 to Aug 25
$64 total
Aug 24 - Aug 25
Total with taxes and fees
6.4/10 (1,220 reviews)
Hotels in Southwest Side with star-rating

5 Star Hotels
9 properties
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