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Our top choices for Southwest Side holiday rentals

1. Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$411
includes taxes & fees
9 Nov - 10 Nov

2. Spacious Apt | 4 Queen Beds | Free Parking
Spacious Apt | 4 Queen Beds | Free ParkingBrighton Park
The price is NZ$666
includes taxes & fees
11 Nov - 12 Nov

3. Sentral Michigan Avenue
Sentral Michigan AvenueDowntown Chicago
9.0 out of 10, Wonderful, (1,406 reviews)
The price is NZ$269
includes taxes & fees
7 Dec - 8 Dec

4. Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park Trendy Studio Apartment in Good SpotHyde Park
10.0 out of 10, Exceptional, (1 review)
The price is NZ$272
includes taxes & fees
12 Nov - 13 Nov

5. Kasa Lake Shore Chicago
Kasa Lake Shore ChicagoDowntown Chicago
8.8 out of 10, Excellent, (85 reviews)
The price is NZ$433
includes taxes & fees
22 Nov - 23 Nov

6. Great Area Logan Square Apt Games Pets - Sleeps 5
Great Area Logan Square Apt Games Pets - Sleeps 5Avondale
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$333
includes taxes & fees
9 Nov - 10 Nov

7. 3BR Complete and Spacious Apartment in Ideal Spot
3BR Complete and Spacious Apartment in Ideal SpotWest Town
8.4 out of 10, Very good, (24 reviews)
The price is NZ$344
includes taxes & fees
9 Nov - 10 Nov

8. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Artistic Loft Rooftop | 13 mins DT | 4 mins LakeUptown
10.0 out of 10, Exceptional, (60 reviews)
The price is NZ$449
includes taxes & fees
9 Nov - 10 Nov

9. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSPBerwyn
9.8 out of 10, Exceptional, (35 reviews)
The price is NZ$316
includes taxes & fees
16 Nov - 17 Nov

10. Chic Suite/Mins to L Train /Laundry/Free Parking
Chic Suite/Mins to L Train /Laundry/Free ParkingOak Park
9.6 out of 10, Exceptional, (75 reviews)
The price is NZ$379
includes taxes & fees
17 Nov - 18 Nov

11. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Regal Stylish Loft Rooftop|13 mins DT |4 mins LakeUptown
9.2 out of 10, Wonderful, (32 reviews)
The price is NZ$449
includes taxes & fees
9 Nov - 10 Nov

12. Chic Urban Retreat Near Wrigley Field w/Parking
Chic Urban Retreat Near Wrigley Field w/ParkingLakeview
10.0 out of 10, Exceptional, (79 reviews)
The price is NZ$753
includes taxes & fees
11 Nov - 12 Nov

13. Private Workspace • Sleeps 4 • Modern and Stylish
Private Workspace • Sleeps 4 • Modern and StylishIrving Park
10.0 out of 10, Exceptional, (7 reviews)
The price is NZ$570
includes taxes & fees
21 Nov - 22 Nov

14. Level Chicago – Old Town
Level Chicago – Old TownDowntown Chicago
9.2 out of 10, Wonderful, (559 reviews)
The price is NZ$407
includes taxes & fees
23 Nov - 24 Nov

15. Chic Studio in the Heart of the Gold Coast
Chic Studio in the Heart of the Gold CoastDowntown Chicago
10.0 out of 10, Exceptional, (1 review)
The price is NZ$377
includes taxes & fees
16 Nov - 17 Nov

16. Wrigleyville Suites
Wrigleyville SuitesLakeview
9.4 out of 10, Exceptional, (49 reviews)
The price is NZ$311
includes taxes & fees
9 Nov - 10 Nov

17. 1BR/1BA City Comfort
1BR/1BA City ComfortLincoln Square
8.6 out of 10, Excellent, (13 reviews)
The price is NZ$279
includes taxes & fees
9 Nov - 10 Nov

18. LIVN Millennium Park Downtown Chicago 1 BR
LIVN Millennium Park Downtown Chicago 1 BRDowntown Chicago
10.0 out of 10, Exceptional, (1 review)
The price is NZ$342
includes taxes & fees
9 Nov - 10 Nov

19. Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Stylish Luxe King bed w/Free Parkng near DT Oak PkOak Park
9.6 out of 10, Exceptional, (115 reviews)
The price is NZ$402
includes taxes & fees
17 Nov - 18 Nov

20. Sleeps 7 • Huge Projector • Designated Workspace
Sleeps 7 • Huge Projector • Designated WorkspaceIrving Park
9.2 out of 10, Wonderful, (12 reviews)
The price is NZ$574
includes taxes & fees
17 Nov - 18 Nov
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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Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake ChicagoDowntown Chicago






















































































































