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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, (1,365 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is HK$1,224
HK$1,437 total
includes taxes & fees
10 Nov - 11 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, (61 reviews)
"Location is perfect"
United States
Mary
The price is HK$1,405
HK$2,137 total
includes taxes & fees
2 Nov - 3 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, (539 reviews)
"Beautiful property, great amenities."
United States
Erik
The price is HK$2,230
HK$2,811 total
includes taxes & fees
4 Nov - 5 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, (283 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is HK$2,017
HK$2,309 total
includes taxes & fees
9 Nov - 10 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, (285 reviews)
"Spent my 30th birthday here & loved every moment of it, we will be back . It’s so peaceful , I really got a peace of mind in this place ."
United States
Brittany
The price is HK$1,193
HK$1,672 total
includes taxes & fees
9 Nov - 10 Nov
Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy
Living area

6. The Silo 4 - Cozy Retreat

The Silo 4 - Cozy Retreat
2.5 star property
Morton
10.0 out of 10, Exceptional, (2 reviews)
"Love this property! It is 100% my go to when I am in town for work which is weekly! The staff is super friendly and accommodating for all needs!"
United States
Troy
The price is HK$502
HK$1,151 total
includes taxes & fees
9 Nov - 10 Nov
The Silo 4 - Cozy Retreat
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, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is HK$1,504
HK$2,593 total
includes taxes & fees
25 Oct - 26 Oct
At Home in Oak Park
A row of single-family homes with a well-maintained lawn and a tree in the foreground.

8. 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
11 Oct - 12 Oct
Nauvoo Vacation Villas & Condos
Living area

9. The Silo 6 - Modern Abode

The Silo 6 - Modern Abode
2.0 star property
Morton
8.8 out of 10, Excellent, (3 reviews)
"Great place! Very clean and close to shooting, restaurants, coffee shops, etc. Very helpful host. Would definitely stay here again!!"
United States
Anne
The price is HK$439
HK$1,080 total
includes taxes & fees
1 Nov - 2 Nov
The Silo 6 - Modern Abode
A modern living room with a dining area, a large window, a flat-screen TV, and a piece of abstract art on the wall.

10. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (13 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$3,045
HK$4,078 total
includes taxes & fees
12 Oct - 13 Oct
LIVN Millennium Park Downtown Chicago 2BR
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

11. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (68 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
The price is HK$980
HK$1,868 total
includes taxes & fees
13 Oct - 14 Oct
Chic Urban Retreat Near Wrigley Field w/Parking
A modern bedroom with a bed, a sofa, and a hanging plant.

12. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (102 reviews)
"Great location and amazing space! Perfect for visiting the city to apartment search for an upcoming move."
United States
Audrey A.
The price is HK$494
HK$1,094 total
includes taxes & fees
2 Nov - 3 Nov
Cozy studio in Andersonville Chicago
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

13. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (288 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveller
The price is HK$531
HK$640 total
includes taxes & fees
11 Oct - 12 Oct
King Bed Non-Smoking
A modern room with a sofa, a dining table, and a window with a view of buildings.

14. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (14 reviews)
"Great property"
United States
duane
The price is HK$3,445
HK$4,606 total
includes taxes & fees
12 Oct - 13 Oct
LIVN West Loop Chicago 2 BR City View
A courtyard with a garden, stone building, and wooden house.

15. 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
9.6 out of 10, Exceptional, (113 reviews)
"We really enjoyed the space, and it was perfect for us."
United States
Nate T.
The price is HK$1,124
HK$2,694 total
includes taxes & fees
14 Oct - 15 Oct
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
A kitchen with a white stove, microwave, and refrigerator, wooden flooring, and light gray walls.

16. Quaint 2 bed in Champaign

Quaint 2 bed in Champaign
Champaign Northwest
9.6 out of 10, Exceptional, (50 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
13 Oct - 14 Oct
Quaint 2 bed in Champaign
Interior

17. Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
9.6 out of 10, Exceptional, (10 reviews)
"Great location with large beds which made it amazing for our group. Easy access to public transport and a cute neighborhood"
United States
Kortnee
The price is HK$4,465
HK$8,251 total
includes taxes & fees
23 Oct - 24 Oct
Premium Urban 4BR - Perfect Mix of Comfort & Location
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

18. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (88 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is HK$840
HK$1,631 total
includes taxes & fees
19 Oct - 20 Oct
Master qtr close to nature & easy urban facilities
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

19. 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, (72 reviews)
"Easy access to the Green Line."
United States
Michael
The price is HK$800
HK$1,860 total
includes taxes & fees
2 Nov - 3 Nov
Chic Suite/Mins to L Train /Laundry/Free Parking
A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

20. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.4 out of 10, Exceptional, (33 reviews)
"Super clean great location short drive to everything we wanted to see!"
United States
eric p.
The price is HK$2,472
HK$5,433 total
includes taxes & fees
14 Oct - 15 Oct
ENVITAE Hotel, 4BR Luxury Modern Apartments
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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"The hotel was very nice. The 29th floor bar was cozy and provided a great atmosphere overlooking the streets of Chicago. The room was spacious enough. I loved the wall art and the wall mural behind the bed. I love it had a microwave!! I like the room had a sitting area where you could dress or visitors could sit. Although when I first walked around the room, the bathroom had few hairs on the sink and there was no liquid soap but it had a small bar soap. It was also weird to have a few stairs in the room to get down to the bed area. As a solo traveler, I didn't like that my room was a corner room. I am not sure if that is the standard for this hotel when booked as a individual stay or booked through hotels.com."
Genita 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection - Magnificent Mile