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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 | Shops
Lincoln Park
9.6 out of 10, Exceptional, (45 reviews)
"Great location. Great place to stay. "
United States
Jill L.
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

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)
"Property is a bit worn, however, furnishings are in good shape and nicely appointed for our stay. Clean upon arrival and great location for an extended stay in Chicago. Host has extra supplies that are helpful- umbrellas, games, laundry detergent that made our stay easier and more enjoyable. Would stay again."
United States
Sara C.
4 BR • Theater Room • Gym • Walk to Lincoln Park!

3. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
9.8 out of 10, Exceptional, (8 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is AED 323
AED 1,978 total
includes taxes & fees
15 Nov - 16 Nov
Theater • Game Room • Gym • Firepit • 4BR Home

4. Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveler
The price is AED 558
AED 3,269 total
includes taxes & fees
17 Nov - 18 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater

5. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (45 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
Chicago Riverhouse with private fenced in oasis

6. Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.6 out of 10, Exceptional, (5 reviews)
"Everyone was super happy with the house and the location."
United States
Rhiannon
The price is AED 408
AED 1,804 total
includes taxes & fees
16 Nov - 17 Nov
Game Room • Fire-pit • Playground • Gym • Billiard

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 bed
Maywood
7.8 out of 10, Good, (36 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is AED 545
AED 1,059 total
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

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)
"We enjoyed our stay at Crimson Manor. The property was super clean and well furnished, and kitchen was well-appointed. Stacey was a very responsive and attentive host. Even when we had difficulty getting into the garage, she had it resolved in 10 minutes. The basement game room is awesome - especially if you have a family! We recommend this property!"
United States
Steve H.
Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...

9. Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking

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

10. Spacious Des Plaines Home - Near Airport, Casino & Arena

Spacious Des Plaines Home - Near Airport, Casino & Arena
Des Plaines
8.0 out of 10, Very good, (2 reviews)
"It was a nice area."
United States
Sherice S.
The price is AED 778
AED 1,740 total
includes taxes & fees
23 Nov - 24 Nov
Spacious Des Plaines Home - Near Airport, Casino & Arena

11. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful place to stay!"
United States
Chasity D.
The price is AED 859
AED 2,463 total
includes taxes & fees
16 Nov - 17 Nov
Vibrant House, Walk to Train, Game Room

12. Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard

Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard
Oak Park
10.0 out of 10, Exceptional, (4 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is AED 691
AED 1,422 total
includes taxes & fees
1 Dec - 2 Dec
Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard

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)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is AED 624
AED 946 total
includes taxes & fees
22 Nov - 23 Nov
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

14. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (91 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is AED 426
AED 763 total
includes taxes & fees
15 Nov - 16 Nov
Master qtr close to nature & easy urban facilities

15. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
Forest Park
10.0 out of 10, Exceptional, (2 reviews)
"Great location, great place to stay, host was friendly. Parking was great. Hoping to be able to stay again in the near future."
United States
LEM R.
The price is AED 705
AED 1,694 total
includes taxes & fees
24 Nov - 25 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line

16. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
10.0 out of 10, Exceptional, (1 review)
"Happy with communication, comfort and location"
United States
Kelly K.
The price is AED 492
AED 1,074 total
includes taxes & fees
7 Dec - 8 Dec
Back Unit Patio, Balcony, Yard, Smart TVs, W/D

17. Premier 9BR Art Deco manor with garage.

Premier 9BR Art Deco manor with garage.
Lakeview
7.4 out of 10, Good, (3 reviews)
"Check in seamless, property was clean and very well appointed, and hosts were responsive, professional and polite. Can’t ask for much more. "
United States
Joel D.
The price is AED 1,935
AED 6,746 total
includes taxes & fees
7 Dec - 8 Dec
Premier 9BR Art Deco manor with garage.

18. Cozy Home | King Bed | 10P | Metra |Chicago Suburb

Cozy Home | King Bed | 10P | Metra |Chicago Suburb
Highland Hills
9.4 out of 10, Exceptional, (3 reviews)
"I booked this property because I was told (before I made the reservation) that the bedroom and one of the bathrooms were on the main floor. I specifically inquired whether my mother-in-law would need to use stairs to access a bedroom and bathroom. In the words of the host, "the main living area, kitchen, two bedrooms and a full bathroom are on the main floor. Only the basement requires the use of steps ". This was not the case. The two bedrooms and a full bathroom are up a flight of 5...
United States
Denise G.
The price is AED 444
AED 1,500 total
includes taxes & fees
18 Nov - 19 Nov
Cozy Home | King Bed | 10P | Metra |Chicago Suburb

19. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (65 reviews)
"It was a great home to stay at house was clean, some dirty sheets left on top of washer but other than that everything was good , will definitely come back"
United States
Brenda M
The price is AED 661
AED 1,293 total
includes taxes & fees
18 Nov - 19 Nov
LUXE 3 BR, 2 BA + Hot Tub

20. Your Next Vacation Home

Your Next Vacation Home
Oakton
9.4 out of 10, Exceptional, (84 reviews)
"It was a very clean place, comfortable furniture and beds e.c.t."
United States
Ronald H.
The price is AED 569
AED 1,081 total
includes taxes & fees
30 Nov - 1 Dec
Your Next Vacation Home
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.

A river with a yellow boat, surrounded by tall buildings and a bridge.

Top reviews in Chicago

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