Lodging Image

Find hotels in Southwest Side, IL from $64

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 7 - Aug 9
In two weeks
Aug 14 - Aug 16

Filter by

Star rating

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Southwest Side hotels

Hotel
Restaurant

1. Holiday Inn Chicago ā€“ Midway Airport S by IHG

Holiday Inn Chicago ā€“ Midway Airport S by IHG
2.5 star property
West Lawn
8.2 out of 10, Very Good, (1,012 reviews)
"a great stay"
United States
Ashley
$141 nightly
The price is $164
Aug 9 - Aug 10
Total with taxes and fees
Holiday Inn Chicago ā€“ Midway Airport S by IHG
Traditional Room, 2 Queen Beds, Non Smoking | Premium bedding, desk, laptop workspace, soundproofing

2. Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
6.2 out of 10, (1,005 reviews)
"Nice , clean, established."
United States
Kevin
$102 nightly
The price is $120
Aug 18 - Aug 19
Total with taxes and fees
Carlton Inn Midway
Exterior

3. Skylark Motel

Skylark Motel
2.0 star property
Garfield Ridge
4.8 out of 10, (133 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."
United States
Jose Francisco Damas
Skylark Motel
Terrace/patio

4. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,634 reviews)
"Great stay."
United States
Dawn
$234 nightly
The price is $278
Aug 31 - Sep 1
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton
Lobby

5. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very Good, (10,185 reviews)
"Great place to stay"
United States
ERIC
$145 nightly
The price is $172
Aug 30 - Aug 31
Total with taxes and fees
Congress Plaza Hotel
Restaurant

6. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
Downtown Chicago
8.2 out of 10, Very Good, (2,754 reviews)
"Good stay!"
United States
Adit
$143 nightly
The price is $170
Aug 30 - Aug 31
Total with taxes and fees
Best Western Grant Park Hotel
Lobby

7. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
Downtown Chicago
7.6 out of 10, Good, (2,711 reviews)
"Great location, clean rooms, would stay here again!"
United States
Adam
$130 nightly
The price is $154
Aug 31 - Sep 1
Total with taxes and fees
Travelodge by Wyndham Downtown Chicago
Exterior

8. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,294 reviews)
"Very helpful front desk staff and friendly cleaners. Very pleasant stay"
United States
Aleace
$167 nightly
The price is $199
Aug 30 - Aug 31
Total with taxes and fees
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Pool

9. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,112 reviews)
"Family friendly property close to sites."
United States
Heather
$161 nightly
The price is $191
Aug 31 - Sep 1
Total with taxes and fees
Hilton Garden Inn Chicago Downtown South Loop
Exterior

10. Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,012 reviews)
"Great location, friendly staff, various amenities for the family."
Canada
kun
$219 nightly
The price is $261
Aug 30 - Aug 31
Total with taxes and fees
Hilton Chicago
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

11. Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,122 reviews)
"good hotel"
United States
Chimere
$194 nightly
The price is $231
Aug 30 - Aug 31
Total with taxes and fees
Holiday Inn & Suites Chicago - Downtown by IHG
Lobby

12. Le MĆ©ridien Essex Chicago

Le MĆ©ridien Essex Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,007 reviews)
"Easy check in and the room was perfect. Had dinner at the restaurant and had a great time. Room was great. One of the best rooms I've stayed at"
United States
Juvey
$158 nightly
The price is $188
Aug 30 - Aug 31
Total with taxes and fees
Le MĆ©ridien Essex Chicago
Lobby

13. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (1,897 reviews)
"Great stay"
United States
Judy
$152 nightly
The price is $181
Aug 17 - Aug 18
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
Lobby

14. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,332 reviews)
"Fantastic hotel!"
Canada
Gillian
$199 nightly
The price is $236
Aug 25 - Aug 26
Total with taxes and fees
Silversmith Hotel Chicago Downtown
Interior detail

15. Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,163 reviews)
"It was nice and in the perfect location."
United States
Teresa
$214 nightly
The price is $254
Aug 30 - Aug 31
Total with taxes and fees
Staypineapple, An Iconic Hotel, The Loop
Outdoor pool, cabanas (surcharge), pool umbrellas

16. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,545 reviews)
"Loved the pool and the close proximity downtown!"
United States
Macy
$161 nightly
The price is $191
Aug 30 - Aug 31
Total with taxes and fees
DoubleTree by Hilton Chicago - Magnificent Mile
Room service - dining

17. The Wade

The Wade
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,963 reviews)
"Great stay and friendly staff!"
Canada
Richard
$149 nightly
The price is $177
Aug 9 - Aug 10
Total with taxes and fees
The Wade
2 restaurants; breakfast, lunch, and dinner served

18. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,803 reviews)
"Great location"
United States
Yolanda
$232 nightly
The price is $276
Aug 30 - Aug 31
Total with taxes and fees
LondonHouse Chicago, Curio Collection by Hilton
Exterior

19. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,459 reviews)
"Just really like this stay and location is fantastic!"
United States
Timothy
$155 nightly
The price is $184
Aug 30 - Aug 31
Total with taxes and fees
Claridge House Chicago, Tapestry Collection by Hilton
Exterior

20. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,707 reviews)
"Great stay!"
United States
Jennifer
$161 nightly
The price is $191
Aug 30 - Aug 31
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Southwest Side attractions

Marquette Park

9.4/10 (3 reviews)
After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
See properties

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.

See all hotels in Southwest Side
An airport with multiple runways, parked airplanes, and a large terminal building.
Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport

Top Southwest Side Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Breakfast is the best ever experienced at a hotel and included in the room rate. Very clean room and friendly staff"
Anthony 3-night trip
Posted less than an hour ago
Hotel Riu Plaza Chicago

More cheap stays in Southwest Side

Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL
$57 nightly
The price is $64 total per night from Aug 11 to Aug 12
$64 total
Aug 11 - Aug 12
Total with taxes and fees

Hotels in Southwest Side with star-rating

Explore a world of travel with Expedia