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

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chicago holiday homes

A modern kitchen with white cabinets, a granite countertop, a coffee machine, and a window with blinds.

1. 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.
The price is £511
includes taxes & fees
9 Nov - 10 Nov
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A dining area with a wooden table, dark chairs, and a chandelier. There are large windows with white curtains, and a view of trees and a car outside.

2. Quiet Stay - Perfect for Family

Quiet Stay - Perfect for Family
Belmont Cragin
Quiet Stay - Perfect for Family
A modern building with a glass facade, surrounded by a courtyard with benches and greenery.

3. Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
10.0 out of 10, Exceptional, (2 reviews)
"From booking to leaving, the experience here was amazing and easy to navigate. Great building and I have never had a more communicative host situation. Would gladly book again."
United States
Erin G.
Envitae Hotel, 4BR Modern Sleek Apartment
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

4. 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.
The price is £433
includes taxes & fees
16 Nov - 17 Nov
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern living room with a white sofa, a white armchair, and a floor lamp.

5. 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 £343
includes taxes & fees
9 Nov - 10 Nov
Game Room • Fire-pit • Playground • Gym • Billiard
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

6. 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 traveller
The price is £648
includes taxes & fees
17 Nov - 18 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

7. 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.
The price is £432
includes taxes & fees
19 Nov - 20 Nov
Chicago Riverhouse with private fenced in oasis
A bunk bed with a ladder, a small table, a potted plant, and a window with blinds.

8. Vintage meets Modern 20 min from Chicago.

Vintage meets Modern 20 min from Chicago.
Calumet City
The price is £285
includes taxes & fees
8 Dec - 9 Dec
Vintage meets Modern 20 min from Chicago.
1-13 (1)

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

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is £417
includes taxes & fees
10 Nov - 11 Nov
Theater • Game Room • Gym • Firepit • 4BR Home
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

10. 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, (35 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is £220
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

11. 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.
The price is £316
includes taxes & fees
9 Nov - 10 Nov
Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...
A single-story house with a covered porch, a front door, and a small garden area.

12. Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
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 £308
includes taxes & fees
23 Nov - 24 Nov
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

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 £186
includes taxes & fees
9 Nov - 10 Nov
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A dining room with a wooden table, black chairs, a red placemat, and a ceiling light fixture.

14. 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 £276
includes taxes & fees
12 Nov - 13 Nov
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
A modern kitchen with a marble countertop, stainless steel appliances, and light wood flooring.

15. 3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare

3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
Addison
The price is £280
includes taxes & fees
9 Nov - 10 Nov
3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

16. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is £269
includes taxes & fees
16 Nov - 17 Nov
LUXE 3 BR, 2 BA + Hot Tub
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

17. 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 £332
includes taxes & fees
9 Nov - 10 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

18. 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 £222
includes taxes & fees
7 Dec - 8 Dec
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

19. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
The price is £484
includes taxes & fees
9 Nov - 10 Nov
Vibrant House, Walk to Train, Game Room
A modern kitchen with stainless steel appliances, a built-in oven, and a dining area with bar stools.

20. 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 £1,325
includes taxes & fees
9 Dec - 10 Dec
Premier 9BR Art Deco manor with garage.
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 Chicago Hotel Reviews

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"Our stay started off not the best but the staff went above and beyond to fix the mistakes. When we checked in the room was very tight and not the best kept. Expedia didnt give the best description of the room so it wasnt the fault of the hotel. The first night was awful though due to our ac being broken, the room was extremely hot and it was hard to sleep. We went down to complaint he next morning and the staff was extremely kind and helpful in getting us switched to a new room. The next room had the same issue, the ac was not working. so we got moved to another room. The next room we stayed in they had upgraded us due to the inconvenience. This room was much bigger and the ac finally worked! The staff being so kind and helpful made us want to stay again. The hotel is older so of course its not going to be perfect but i can handle the hotel not being perfect when the staff actually cares enough to try to make the stay as comfortable as possible. because of that i will be staying at this location again!"
Julia 3-night trip
Posted 6 hours ago
Hotel Saint Clair- Magnificent Mile

Find out more about Chicago

Chicago Holiday Homes information

Number of reviews
187
Accommodation
773 Holiday Homes
Lowest Price
£186
Highest Price
£1,325

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