Southwest Side Villas

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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

West Lawn

Paulina

HK$1,285 total

includes taxes & fees

8 Nov - 9 Nov

A van parked in front of a building with a balcony and a sign indicating a parking area.

2. Carlton Inn Midway

Archer Heights

Icaro

HK$965 total

includes taxes & fees

13 Oct - 14 Oct

A two-story brick building with a white door and windows, a tree in front, and a parked truck.

3. Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Brighton Park

Yiu S.

HK$1,850 total

includes taxes & fees

13 Oct - 14 Oct

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

Brighton Park

Damary T.

HK$2,183 total

includes taxes & fees

13 Oct - 14 Oct

A motel with a two-story structure, numbered rooms, and a parking area with a car.

5. Rainbow Motel

Garfield Ridge

Jerry

HK$644 total

includes taxes & fees

12 Oct - 13 Oct

A bathroom with a bathtub, a shower curtain, a towel rack, and a window.

6. Spacious Apt | 4 Queen Beds | Free Parking

Brighton Park

HK$3,194 total

includes taxes & fees

22 Oct - 23 Oct

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

7. Carleton of Oak Park

Oak Park

Brad

HK$1,066 total

includes taxes & fees

12 Oct - 13 Oct

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

Downtown Chicago

John

HK$1,693 total

includes taxes & fees

29 Oct - 30 Oct

9. Hilton Chicago

Downtown Chicago

Anna

HK$1,777 total

includes taxes & fees

30 Oct - 31 Oct

A hotel entrance with a covered parking area, clear signage, and a well-lit facade.

10. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

HK$843 total

includes taxes & fees

21 Oct - 22 Oct

A restaurant with outdoor seating overlooking a city skyline.

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

Downtown Chicago

Shanequa

HK$2,408 total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.

12. Best Western Grant Park Hotel

Downtown Chicago

Shelby Ryann

HK$1,503 total

includes taxes & fees

25 Oct - 26 Oct

A large hotel with a classic architectural style, featuring multiple floors and a prominent entrance.

13. Congress Plaza Hotel

Downtown Chicago

Katimah

HK$1,190 total

includes taxes & fees

1 Nov - 2 Nov

A multi-story hotel with a prominent corner location, large windows, and a red awning.

14. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

HK$1,061 total

includes taxes & fees

2 Nov - 3 Nov

A modern outdoor terrace with multiple dining tables and chairs, surrounded by high-rise buildings.

15. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Jayne

HK$1,697 total

includes taxes & fees

25 Oct - 26 Oct

A Hampton Inn hotel with a modern facade, large windows, and a welcoming entrance.

16. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

Jennifer

HK$1,128 total

includes taxes & fees

1 Nov - 2 Nov

A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

17. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Joel

HK$1,801 total

includes taxes & fees

1 Nov - 2 Nov

A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.

18. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

HK$1,713 total

includes taxes & fees

25 Oct - 26 Oct

A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.

19. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Adhba

HK$1,052 total

includes taxes & fees

3 Nov - 4 Nov

A circular outdoor seating area with a fire feature, surrounded by greenery and a view of a brick building through large windows.

20. The Emily Hotel

Downtown Chicago

Leslie

HK$1,538 total

includes taxes & fees

1 Nov - 2 Nov

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Top Southwest Side Hotel Reviews

Freehand Chicago

8/10 Good

"Great location and staff! I also loved the onsite laundry option and water bottle filler in the gym. The room had an “off” (old? Musty?) smell to it but was otherwise alright."

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"CQ is a reliable brand as this property demonstrated. I was particularly pleased with the size of the room and fitness facility. Best CQ I have stayed at and would return. Two quibbles: No desk lamp, therefore a dark work area and no hand soap (use body gel? I bring my own). Housekeeping excellent."

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