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Illinois Holiday Rentals

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Top Cities in Illinois

A city skyline with modern skyscrapers and a river with boats and people in the foreground.
Holiday RentalsHoliday Rentals

Chicago

Chicago

Our top choices for Illinois holiday rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,384 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is HK$1,124
HK$1,319 total
includes taxes & fees
9 Nov - 10 Nov
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (73 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is HK$1,405
HK$2,063 total
includes taxes & fees
1 Nov - 2 Nov
Kasa Lake Shore Chicago
A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (544 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is HK$2,043
HK$2,592 total
includes taxes & fees
1 Nov - 2 Nov
Level Chicago – Old Town
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

4. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (289 reviews)
"Very charming hotel we really enjoyed having breakfast in the morning and ability to have a bottle of wine with dinner at Knight and our bag was very comfortable and nice having the ability to open the window and have some fresh air all in all very charming"
United States
Kathleen
The price is HK$1,570
HK$1,797 total
includes taxes & fees
4 Nov - 5 Nov
The Gem Museum Suites
A rustic cabin with a dining area, a bicycle, and a sign reading "Vangelis".

5. Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy
2.0 star property
Ottawa
9.8 out of 10, Exceptional, (297 reviews)
"Everything was wonderful"
United States
Maria
The price is HK$1,193
HK$1,672 total
includes taxes & fees
19 Nov - 20 Nov
Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

6. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (71 reviews)
"The app isn’t letting me give 5 stars but I would give 5 stars for all categories. It was perfect for our needs. Two adults and two kids. Perfect location and easy to get in and out with our car off the street. Beds were comfy and the main rooms were spacious. They were super responsive for our last minute booking. Would definitely stay here again!"
United States
Bridget
The price is HK$797
HK$1,657 total
includes taxes & fees
4 Nov - 5 Nov
Chic Urban Retreat Near Wrigley Field w/Parking
Terrace/patio

7. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (13 reviews)
"The apartment was clean and had everything we needed for a comfortable stay. Highly recommended!"
Italy
Marco
The price is HK$1,671
HK$2,785 total
includes taxes & fees
25 Oct - 26 Oct
At Home in Oak Park
A modern living room with a dining area, a large window, a flat-screen TV, and a piece of abstract art on the wall.

8. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$1,727
HK$2,317 total
includes taxes & fees
25 Oct - 26 Oct
LIVN Millennium Park Downtown Chicago 2BR
A row of single-family homes with a well-maintained lawn and a tree in the foreground.

9. Nauvoo Vacation Villas & Condos

Nauvoo Vacation Villas & Condos
3.0 star property
Nauvoo
9.8 out of 10, Exceptional, (459 reviews)
"A great place to stay!"
United States
Renae
The price is HK$1,130
HK$1,198 total
includes taxes & fees
22 Oct - 23 Oct
Nauvoo Vacation Villas & Condos
A modern bedroom with a bed, a sofa, and a hanging plant.

10. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (105 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
The price is HK$494
HK$1,094 total
includes taxes & fees
2 Nov - 3 Nov
Cozy studio in Andersonville Chicago
A modern kitchen with a central island, bar stools, and a dining table.

11. River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.8 out of 10, Exceptional, (15 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
The price is HK$1,883
HK$4,671 total
includes taxes & fees
18 Nov - 19 Nov
River North Private Deck With In and Out Parking
A waiting area with two white chairs, a white table, a television mounted on the wall, and an exit door.

12. Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
Downtown Chicago
10.0 out of 10, Exceptional, (13 reviews)
"Best location"
United States
Eric Dallas
The price is HK$1,334
HK$3,710 total
includes taxes & fees
25 Oct - 26 Oct
Downtown Chicago Stay with Free In & Out Parking 3
Communal Lounge

13. 4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.6 out of 10, Exceptional, (31 reviews)
"This was a great property. It was easy to access, easy transportation near by, Whole Foods is right around the corner and the neighborhood is very pleasant. Will definitely stay here again."
United States
Josh
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
A modern bedroom with a brick wall, a large bed, a sofa, a nightstand, and a mirror.

14. LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is HK$1,797
HK$2,420 total
includes taxes & fees
25 Oct - 26 Oct
LIVN West Loop Chicago King Studio
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

15. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (289 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveller
The price is HK$531
HK$641 total
includes taxes & fees
25 Oct - 26 Oct
King Bed Non-Smoking
A courtyard with a garden, stone building, and wooden house.

16. Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.8 out of 10, Exceptional, (116 reviews)
"The host communicated well and the place was great. Fantastic location."
United States
azanayed
The price is HK$1,124
HK$2,694 total
includes taxes & fees
26 Oct - 27 Oct
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

17. Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (73 reviews)
"Easy access to the Green Line."
United States
Michael
The price is HK$720
HK$1,822 total
includes taxes & fees
2 Nov - 3 Nov
Chic Suite/Mins to L Train /Laundry/Free Parking
A kitchen with a white stove, microwave, and refrigerator, wooden flooring, and light gray walls.

18. Quaint 2 bed in Champaign

Quaint 2 bed in Champaign
Champaign Northwest
9.6 out of 10, Exceptional, (54 reviews)
"It was perfect for our small family and had everything we needed - easy access from the highway and a quick ride to campus for the football game."
United States
Allison
The price is HK$883
HK$1,208 total
includes taxes & fees
22 Oct - 23 Oct
Quaint 2 bed in Champaign
A modern kitchen with a dining area, large windows, and a city view.

19. Modern 2BR Retreat Near Old Town & Lincoln Park

Modern 2BR Retreat Near Old Town & Lincoln Park
Near North Side
9.2 out of 10, Wonderful, (23 reviews)
"Such a great apartment! Perfect size for 2 couples and the location was excellent. I’d highly recommend staying here- we’ll definitely stay again when we return to Chicago!"
United States
Josephine P.
The price is HK$1,342
HK$4,736 total
includes taxes & fees
26 Oct - 27 Oct
Modern 2BR Retreat Near Old Town & Lincoln Park
An indoor swimming pool with a hexagonal tiled floor, wooden beams on the ceiling, and a view of the outdoors through large windows.

20. Scenic Galena Retreat | 2 Kings | Golf Course Views | Cozy Fireplace | Pool

Scenic Galena Retreat | 2 Kings | Golf Course Views | Cozy Fireplace | Pool
The Galena Territory
10.0 out of 10, Exceptional, (101 reviews)
"Lovely, quiet place to stay"
United States
Bethanie B.
The price is HK$798
HK$2,197 total
includes taxes & fees
26 Oct - 27 Oct
Scenic Galena Retreat | 2 Kings | Golf Course Views | Cozy Fireplace | Pool
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 Illinois Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Our favorite downtown hotel!!"
Judith 2-night trip
Posted less than an hour ago
Congress Plaza Hotel