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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan
No exact matches found, but these alternatives could be just right

Recommended hotels in Southwest Side

A Holiday Inn hotel with a parking lot and several cars parked in front.

1. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.2 out of 10, Very good, (1,011 reviews)
"the staff is very friendly and rooms are clean"
United States
Paulina
The price is HK$1,091
HK$1,359 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Chicago – Midway Airport S by IHG
A van parked in front of a building with a balcony and a sign indicating a parking area.

2. Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
6.0 out of 10, (1,014 reviews)
"It’s very Good, good location, good parking, good room and good employees"
United States
Icaro
The price is HK$822
HK$965 total
includes taxes & fees
13 Oct - 14 Oct
Carlton Inn Midway
Exterior

3. Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade

Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
Brighton Park
9.4 out of 10, Exceptional, (13 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
The price is HK$579
HK$2,191 total
includes taxes & fees
13 Oct - 14 Oct
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
A two-story brick building with a white door, a stop sign, and a fire hydrant on the sidewalk.

4. Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
United States
Rachel
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
A bathroom with a bathtub, a shower curtain, a towel rack, and a window.

5. Spacious Apt | 4 Queen Beds | Free Parking

Spacious Apt | 4 Queen Beds | Free Parking
Brighton Park
The price is HK$990
HK$3,101 total
includes taxes & fees
22 Oct - 23 Oct
Spacious Apt | 4 Queen Beds | Free Parking
A motel with a two-story structure, numbered rooms, and a parking area with a car.

6. Rainbow Motel

Rainbow Motel
2.0 star property
Garfield Ridge
5.4 out of 10, (64 reviews)
"Great value for the price. Staff was very friendly."
United States
Jerry
The price is HK$658
HK$772 total
includes taxes & fees
8 Oct - 9 Oct
Rainbow Motel
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

7. Carleton of Oak Park

Carleton of Oak Park
3.0 star property
Oak Park
9.2 out of 10, Wonderful, (1,185 reviews)
"Definitely a boutique hotel, but we'll maintained and in a good area with good eateries close."
United States
Brad
The price is HK$960
HK$1,066 total
includes taxes & fees
21 Oct - 22 Oct
Carleton of Oak Park
A hotel room with a large bed, a nightstand with a lamp, a wall clock, and a window with curtains.

8. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,238 reviews)
"The room was clean and the building was nostalgic."
United States
John
The price is HK$1,349
HK$1,603 total
includes taxes & fees
3 Nov - 4 Nov
Hilton Vacation Club Hotel Blake Chicago
A large, historic building with a central courtyard surrounded by trees.

9. Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,375 reviews)
"Friendly staff, great location"
Canada
Anna
The price is HK$1,301
HK$1,777 total
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
A restaurant with outdoor seating overlooking a city skyline.

10. 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, (2,723 reviews)
"Amazing place to stay"
United States
Shanequa
The price is HK$1,798
HK$2,408 total
includes taxes & fees
1 Nov - 2 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
A hotel entrance with a covered parking area, clear signage, and a well-lit facade.

11. SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard
2.5 star property
Highland Hills
9.0 out of 10, Wonderful, (3,051 reviews)
"I really enjoyed my stay. Will definitely stay here again."
Canada
Blessing
The price is HK$794
HK$881 total
includes taxes & fees
13 Oct - 14 Oct
SureStay Plus Hotel by Best Western Chicago Lombard
A large hotel with a classic architectural style, featuring multiple floors and a prominent entrance.

12. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,198 reviews)
"Nice stay"
United States
Katimah
The price is HK$1,000
HK$1,189 total
includes taxes & fees
1 Nov - 2 Nov
Congress Plaza Hotel
A multi-story hotel with a prominent corner location, large windows, and a red awning.

13. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
Downtown Chicago
7.8 out of 10, Good, (2,889 reviews)
"Great stay"
United States
Sandra
The price is HK$876
HK$1,041 total
includes taxes & fees
2 Nov - 3 Nov
Travelodge by Wyndham Downtown Chicago
A modern outdoor terrace with multiple dining tables and chairs, surrounded by high-rise buildings.

14. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,512 reviews)
"Excellent choice for a weeks stay."
United States
Jayne
The price is HK$1,427
HK$1,697 total
includes taxes & fees
25 Oct - 26 Oct
Homewood Suites by Hilton Chicago Downtown South Loop
A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.

15. 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, (2,180 reviews)
"Great place to stay at"
United States
Aran
The price is HK$1,447
HK$1,721 total
includes taxes & fees
25 Oct - 26 Oct
Hilton Garden Inn Chicago Downtown South Loop
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

16. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,306 reviews)
"A great hotel in a bustling area. We had a great stay."
United States
Joel
The price is HK$1,514
HK$1,801 total
includes taxes & fees
1 Nov - 2 Nov
Hyatt House Chicago/West Loop-Fulton Market
A tall, modern building with a glass facade and the name "Essen Sex Inn" on the top.

17. Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,005 reviews)
"Amazing location, super helpful staff, and clean/comfortable rooms. I stay here every time I am in town."
United States
Kayla Rene
The price is HK$1,938
HK$2,444 total
includes taxes & fees
30 Oct - 31 Oct
Le Méridien Essex Chicago
A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.

18. Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,285 reviews)
"Staff were very friendly and location is perfect"
United States
Adhba
The price is HK$870
HK$1,052 total
includes taxes & fees
2 Nov - 3 Nov
Hotel Saint Clair- Magnificent Mile
A circular outdoor seating area with a fire feature, surrounded by greenery and a view of a brick building through large windows.

19. The Emily Hotel

The Emily Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,350 reviews)
"Great modern hotel in a wonderful location! It’s within walking distance of the train station and surrounded by so many great restaurants and bars. The hotel’s restaurant was soooo yummy and incredibly convenient, too! Would definitely stay here again!"
United States
Leslie
The price is HK$1,342
HK$1,596 total
includes taxes & fees
1 Nov - 2 Nov
The Emily Hotel
A modern hotel with a corner location, large windows, and a green awning.

20. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
3.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,573 reviews)
"Location and great breakfast"
United States
Catherine
The price is HK$1,107
HK$1,316 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Chicago Downtown
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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Great location and there is parking close by in a garage for $40 per night. The hotel itself is nice but the room we stayed in had stained carpets and couch cushions. Assuming all rooms are alike, rooms need a deep clean and some updates. Overall, pretty solid stay if you’re on a budget but want to stay in a quiet and old-money neighborhood"
Yevgeniy 4-night trip
Posted 1 hour ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Southwest Side

Southwest Side Villas information

Number of reviews
25,265
Accommodation
1 Villas
Lowest Price
HK$772
Highest Price
HK$3,101