Find hotels in Southwest Side, IL from $66
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Our top choices for Southwest Side hotels
1. Holiday Inn Chicago ā Midway Airport S by IHG
Holiday Inn Chicago ā Midway Airport S by IHGWest Lawn
8.2 out of 10, Very Good, (1,002 reviews)
"a great stay"
Ashley
$128 nightly
The price is $148
Aug 9 - Aug 10
Total with taxes and fees
2. Carlton Inn Midway
Carlton Inn MidwayArcher Heights
6.2 out of 10, (1,001 reviews)
"Nice , clean, established."
Kevin
$107 nightly
The price is $126
Aug 3 - Aug 4
Total with taxes and fees
3. Skylark Motel
Skylark MotelGarfield Ridge
4.6 out of 10, (131 reviews)
"The towels were super thin and old, the bedding was stained, the bathtub was sagging, and the water wouldn't drain! Someone always had to let me into the building; it felt like a run-down tenement, not a motel."
Jose Francisco Damas
$99 nightly
The price is $116
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, (2,621 reviews)
"Nice Stay"
Morgan
$215 nightly
The price is $256
Aug 30 - Aug 31
Total with taxes and fees
5. Congress Plaza Hotel
Congress Plaza HotelDowntown Chicago
8.0 out of 10, Very Good, (10,163 reviews)
"Great place to stay"
ERIC
$142 nightly
The price is $169
Aug 31 - Sep 1
Total with taxes and fees
6. Best Western Grant Park Hotel
Best Western Grant Park HotelDowntown Chicago
8.2 out of 10, Very Good, (2,751 reviews)
"Good stay!"
Adit
$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, (2,700 reviews)
"Great location, clean rooms, would stay here again!"
Adam
$121 nightly
The price is $144
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, (1,291 reviews)
"Very helpful front desk staff and friendly cleaners. Very pleasant stay"
Aleace
$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, (2,103 reviews)
"helpful staff, great location, comfortable rooms and great views"
Jordan Leigh
$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, (3,000 reviews)
"Great location, friendly staff, various amenities for the family."
kun
$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, (1,113 reviews)
"Great Stay.
Perfect area for activities, clean room, and wonderful staff member who showed excellent hospitality and convenience."
Erick
$164 nightly
The price is $195
Aug 30 - Aug 31
Total with taxes and fees
12. Le MĆ©ridien Essex Chicago
Le MĆ©ridien Essex ChicagoDowntown Chicago
9.0 out of 10, Wonderful, (1,002 reviews)
"Room was quiet and clean"
Robert
$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, (1,864 reviews)
"Great stay"
Judy
$144 nightly
The price is $172
Aug 31 - Sep 1
Total with taxes and fees
14. Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownDowntown Chicago
9.4 out of 10, Exceptional, (2,328 reviews)
"Fantastic hotel!"
Gillian
$203 nightly
The price is $242
Aug 30 - Aug 31
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, (1,157 reviews)
"It was nice and in the perfect location."
Teresa
$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, (2,541 reviews)
"Loved the pool and the close proximity downtown!"
Macy
$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, (3,795 reviews)
"Great location"
Yolanda
$235 nightly
The price is $279
Aug 30 - Aug 31
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, (1,454 reviews)
"Just really like this stay and location is fantastic!"
Timothy
$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, (4,683 reviews)
"Great stay!"
Jennifer
$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
Travelodge by Wyndham Downtown Chicago
10/10 Excellent
More cheap stays in Southwest Side
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
$59 nightly
The price is $66 total per night from Aug 9 to Aug 10
$66 total
Aug 9 - Aug 10
Total with taxes and fees
6.4/10 (1,217 reviews)
Hotels in Southwest Side with star-rating
5 Star Hotels
9 properties
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