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Southwest Side Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Southwest Side holiday rentals

Games room

1. 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$565
HK$2,107 total
includes taxes & fees
13 Oct - 14 Oct
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
A living room with a grey sofa, two chairs, a coffee table, and a small side table.

2. 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
The price is HK$1,059
HK$2,684 total
includes taxes & fees
7 Oct - 8 Oct
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
A compact kitchen with a dining table, a refrigerator, and a trash can.

3. Spacious Apt | 4 Queen Beds | Free Parking

Spacious Apt | 4 Queen Beds | Free Parking
Brighton Park
The price is HK$1,027
HK$3,147 total
includes taxes & fees
22 Oct - 23 Oct
Spacious Apt | 4 Queen Beds | Free Parking
A modern building with the name 'SENIORAL' prominently displayed on the facade.

4. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,353 reviews)
"Nice room, will stay again, highly recommend:)"
United States
Reina
The price is HK$1,249
HK$1,697 total
includes taxes & fees
26 Oct - 27 Oct
Sentral Michigan Avenue
Lake

5. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (50 reviews)
"Location is perfect"
United States
Mary
The price is HK$1,475
HK$2,221 total
includes taxes & fees
4 Nov - 5 Nov
Kasa Lake Shore Chicago
A modern kitchen with a large island, bar stools, and a city view.

6. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (535 reviews)
"Location and facility was very nice"
United States
Brian
The price is HK$1,781
HK$2,285 total
includes taxes & fees
2 Nov - 3 Nov
Level Chicago – Old Town
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

7. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (277 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is HK$1,577
HK$1,806 total
includes taxes & fees
29 Oct - 30 Oct
The Gem Museum Suites
Terrace/patio

8. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is HK$1,504
HK$2,593 total
includes taxes & fees
25 Oct - 26 Oct
At Home in Oak Park
A modern living room with large windows, a flat-screen TV, a sofa, a coffee table, and a dining area with stools and a small table.

9. Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (28 reviews)
"Great location. "
United States
Tom S.
The price is HK$2,087
HK$5,637 total
includes taxes & fees
28 Oct - 29 Oct
Modern West Loop Gem-City Views & Prime Location 6
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

10. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (68 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
The price is HK$1,099
HK$2,004 total
includes taxes & fees
13 Oct - 14 Oct
Chic Urban Retreat Near Wrigley Field w/Parking
A hotel room with a large grey sofa, a small table with a copper pot, a red lamp, and a bed with white linens.

11. LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is HK$1,993
HK$2,660 total
includes taxes & fees
7 Oct - 8 Oct
LIVN Millennium Park Downtown Chicago 1 BR
A modern room with a sofa, a dining table, and a window with a view of buildings.

12. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (12 reviews)
"Great property"
United States
duane
The price is HK$5,219
HK$6,959 total
includes taxes & fees
8 Oct - 9 Oct
LIVN West Loop Chicago 2 BR City View
Private kitchen

13. Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
The price is HK$589
HK$1,690 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

14. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.2 out of 10, Very good, (22 reviews)
"absolutely would stay here again. Great property and great communcation"
United States
Daniel J.
The price is HK$1,475
HK$2,803 total
includes taxes & fees
26 Oct - 27 Oct
3BR Complete and Spacious Apartment in Ideal Spot
A rooftop terrace with a brick wall, large windows, and a metal railing.

15. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (59 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is HK$942
HK$2,617 total
includes taxes & fees
6 Oct - 7 Oct
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A modern living room with a blue sofa, a patterned rug, and a television.

16. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is HK$534
HK$1,672 total
includes taxes & fees
13 Oct - 14 Oct
Great Area Logan Square Apt Games Pets - Sleeps 5
A bedroom with a bed, a wardrobe, a bench, and a floor lamp.

17. Wabash 4BR - Pool, Free In & Out Parking 4

Wabash 4BR - Pool, Free In & Out Parking 4
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Nice place to stay."
United States
William H.
The price is HK$3,029
HK$7,041 total
includes taxes & fees
21 Oct - 22 Oct
Wabash 4BR - Pool, Free In & Out Parking 4
A building with a white exterior and a tree with white blossoms in front.

18. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is HK$1,887
HK$3,032 total
includes taxes & fees
21 Oct - 22 Oct
Historic Oak Park Residence
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

19. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.6 out of 10, Exceptional, (8 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is HK$552
HK$2,366 total
includes taxes & fees
26 Oct - 27 Oct
Sleeps 7 • Huge Projector • Designated Workspace
A rooftop terrace with a fire pit, seating area, and a city skyline view.

20. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
West Town
9.8 out of 10, Exceptional, (6 reviews)
"Very happy with our stay. Loved the rooftop views! The host was very friendly and welcoming."
United States
Jessica C.
The price is HK$846
HK$1,819 total
includes taxes & fees
4 Nov - 5 Nov
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
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 MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"Really nice place"
Yesenia 2-night trip
Posted less than an hour ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

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