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Our top choices for Chicago vacation homes

1. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park Cozy 3bd Home near Zoo | Lake | ShopsLincoln Park
9.6 out of 10, Exceptional, (45 reviews)

2. 4 BR • Theater Room • Gym • Walk to Lincoln Park!
4 BR • Theater Room • Gym • Walk to Lincoln Park!Lincoln Park
9.0 out of 10, Wonderful, (2 reviews)

3. Theater • Game Room • Gym • Firepit • 4BR Home
Theater • Game Room • Gym • Firepit • 4BR HomeBelmont Cragin
9.8 out of 10, Exceptional, (8 reviews)
The price is AED 323
AED 1,978 total
includes taxes & fees
15 Nov - 16 Nov

4. Sleeps 18 • 8BR • Game Room • Gym • Theater
Sleeps 18 • 8BR • Game Room • Gym • TheaterPortage Park
10.0 out of 10, Exceptional, (10 reviews)
The price is AED 558
AED 3,269 total
includes taxes & fees
17 Nov - 18 Nov

5. Chicago Riverhouse with private fenced in oasis
Chicago Riverhouse with private fenced in oasisNorth Park
10.0 out of 10, Exceptional, (45 reviews)

6. Game Room • Fire-pit • Playground • Gym • Billiard
Game Room • Fire-pit • Playground • Gym • BilliardBelmont Cragin
9.6 out of 10, Exceptional, (5 reviews)
The price is AED 408
AED 1,804 total
includes taxes & fees
16 Nov - 17 Nov

7. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bedMaywood
7.8 out of 10, Good, (36 reviews)
The price is AED 545
AED 1,059 total
includes taxes & fees
16 Nov - 17 Nov

8. Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...
Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...Brookfield
10.0 out of 10, Exceptional, (1 review)

9. Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage ParkingOak Park
The price is AED 624
AED 1,337 total
includes taxes & fees
15 Nov - 16 Nov

10. Spacious Des Plaines Home - Near Airport, Casino & Arena
Spacious Des Plaines Home - Near Airport, Casino & ArenaDes Plaines
8.0 out of 10, Very good, (2 reviews)
The price is AED 778
AED 1,740 total
includes taxes & fees
23 Nov - 24 Nov

11. Vibrant House, Walk to Train, Game Room
Vibrant House, Walk to Train, Game RoomBrookfield
10.0 out of 10, Exceptional, (13 reviews)
The price is AED 859
AED 2,463 total
includes taxes & fees
16 Nov - 17 Nov

12. Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard
Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly YardOak Park
10.0 out of 10, Exceptional, (4 reviews)
The price is AED 691
AED 1,422 total
includes taxes & fees
1 Dec - 2 Dec

13. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.Westmont
9.6 out of 10, Exceptional, (7 reviews)
The price is AED 624
AED 946 total
includes taxes & fees
22 Nov - 23 Nov

14. Master qtr close to nature & easy urban facilities
Master qtr close to nature & easy urban facilitiesRiverwoods
9.8 out of 10, Exceptional, (91 reviews)
The price is AED 426
AED 763 total
includes taxes & fees
15 Nov - 16 Nov

15. Classic Forest Park Foursquare < 1 Mi to Blue Line
Classic Forest Park Foursquare < 1 Mi to Blue LineForest Park
10.0 out of 10, Exceptional, (2 reviews)
The price is AED 705
AED 1,694 total
includes taxes & fees
24 Nov - 25 Nov

16. Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Back Unit Patio, Balcony, Yard, Smart TVs, W/DWestmont
10.0 out of 10, Exceptional, (1 review)
The price is AED 492
AED 1,074 total
includes taxes & fees
7 Dec - 8 Dec

17. Premier 9BR Art Deco manor with garage.
Premier 9BR Art Deco manor with garage.Lakeview
7.4 out of 10, Good, (3 reviews)
The price is AED 1,935
AED 6,746 total
includes taxes & fees
7 Dec - 8 Dec

18. Cozy Home | King Bed | 10P | Metra |Chicago Suburb
Cozy Home | King Bed | 10P | Metra |Chicago SuburbHighland Hills
9.4 out of 10, Exceptional, (3 reviews)
The price is AED 444
AED 1,500 total
includes taxes & fees
18 Nov - 19 Nov

19. LUXE 3 BR, 2 BA + Hot Tub
LUXE 3 BR, 2 BA + Hot TubElmhurst
8.6 out of 10, Excellent, (65 reviews)
The price is AED 661
AED 1,293 total
includes taxes & fees
18 Nov - 19 Nov

20. Your Next Vacation Home
Your Next Vacation HomeOakton
9.4 out of 10, Exceptional, (84 reviews)
The price is AED 569
AED 1,081 total
includes taxes & fees
30 Nov - 1 Dec
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.
Chicago and related destinations
Towering skyscrapers frame the stunning Millennium Park where 'The Bean' reflects the city's vibrant energy. Cruise along the Chicago River for spectacular architecture views or catch a Cubs game at historic Wrigley Field.

Top reviews in Chicago

Hilton Vacation Club Hotel Blake Chicago
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