Illinois Holiday Rentals

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Top Cities in Illinois

Chicago featuring a skyscraper and a city as well as a family
Holiday RentalsHoliday Rentals

Chicago

Chicago

Our top choices for Illinois holiday rentals

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1026)
"My favorite place to stay hands-down"
United States
Michele
The price is HK$918
HK$1,306 total
includes taxes & fees
5 Jan - 6 Jan 2026
Sentral Michigan Avenue
Front of property
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is HK$1,023
HK$1,201 total
includes taxes & fees
30 Dec - 31 Dec
Chicago luxury home suites
Business centre
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Front of property – evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (406)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Interior
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

Gold Coast Living: Modern Studio Unit
10.0 out of 10, Exceptional, (5)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is HK$536
HK$1,286 total
includes taxes & fees
4 Jan - 5 Jan 2026
Gold Coast Living: Modern Studio Unit
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

Twice as Nice: Chic 2BR Stay with Style & Space
9.8 out of 10, Exceptional, (16)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is HK$536
HK$1,481 total
includes taxes & fees
1 Jan - 2 Jan 2026
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (5)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is HK$490
HK$1,309 total
includes taxes & fees
4 Jan - 5 Jan 2026
West Loop Living – Bright 1BR
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$490
HK$1,309 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Apartment in Downtown Chicago

Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (10)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$490
HK$1,309 total
includes taxes & fees
1 Jan - 2 Jan 2026
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is HK$490
HK$1,309 total
includes taxes & fees
7 Jan - 8 Jan 2026
The One: A 1BR Stay That Feels Like Home
Exterior
Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy

Cabin in Ottawa

Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.8 out of 10, Exceptional, (101)
"Nice place "
United States
roxana
The price is HK$925
HK$1,371 total
includes taxes & fees
4 Jan - 5 Jan 2026
Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy
Private kitchen
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is HK$3,039
HK$5,200 total
includes taxes & fees
30 Dec - 31 Dec
ENVITAE Hotel 4 Bedroom Luxury Apartments
Restaurant
Yugo Guest Suites

Aparthotel in Urbana

Yugo Guest Suites
4.0 star property
8.8 out of 10, Excellent, (135)
"The room was spacious and clean."
United States
Jinghai
Yugo Guest Suites
Desk, iron/ironing board, WiFi, bed sheets
Relaxing Chicago Studio

Apartment in Edgewater

Relaxing Chicago Studio
10.0 out of 10, Exceptional, (43)
"Had a great stay. Great location. "
United States
Justin
The price is HK$544
HK$1,295 total
includes taxes & fees
5 Jan - 6 Jan 2026
Relaxing Chicago Studio
Exterior
Nauvoo Vacation Villas & Condos

Condo in Nauvoo

Nauvoo Vacation Villas & Condos
3.0 star property
9.8 out of 10, Exceptional, (424)
"Very nice comfortable property"
United States
Carie
The price is HK$1,080
HK$1,183 total
includes taxes & fees
30 Dec - 31 Dec
Nauvoo Vacation Villas & Condos
TV
Nice 1BR Spot, Unwind & Relax

Apartment in Lincoln Square

Nice 1BR Spot, Unwind & Relax
9.6 out of 10, Exceptional, (25)
"Great stay"
United States
Kayla K.
The price is HK$490
HK$1,309 total
includes taxes & fees
1 Jan - 2 Jan 2026
Nice 1BR Spot, Unwind & Relax
Terrace/patio
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Apartment in Uptown

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
10.0 out of 10, Exceptional, (48)
"Clean and quiet, perfect for nights to rest after exploring the city"
United States
Joe T.
The price is HK$494
HK$1,989 total
includes taxes & fees
13 Jan - 14 Jan 2026
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Fridge, microwave, oven, coffee/tea maker
Sassafras Ridge Log Cabin by Garden of the Gods in the Shawnee National Forest

Cabin in Elizabethtown

Sassafras Ridge Log Cabin by Garden of the Gods in the Shawnee National Forest
9.8 out of 10, Exceptional, (102)
"We really enjoyed our stay. The cabin was cozy and had everything you need. The fire pit was a nice way to end the day"
United States
Daniel W.
The price is HK$614
HK$1,103 total
includes taxes & fees
30 Dec - 31 Dec
Sassafras Ridge Log Cabin by Garden of the Gods in the Shawnee National Forest
Exterior
A Little Slice Of Heaven

Cabin in Marion

A Little Slice Of Heaven
10.0 out of 10, Exceptional, (70)
"Cozy, comfortable spot to enjoy while exploring the area."
United States
Ariel T.
The price is HK$933
HK$1,423 total
includes taxes & fees
3 Jan - 4 Jan 2026
A Little Slice Of Heaven
Private kitchen
The Gem Museum Suites

Aparthotel in Downtown Evanston

The Gem Museum Suites
3.5 star property
9.4 out of 10, Exceptional, (100)
"Lovely stay with helpful staff excellent location. Breakfast is a wonderful full dining experience -no pre packaged chain hotel offerings. One can easily walk to shopping, dining, cafes and Lake Michigan. Rooms very clean with lots of storage /closet space. Mini kitchens are fully equipped with new appliances that all work! Only comment is that bed and pillows were very firm and made it uncomfortable to sleep-this is the reason for 4 stars and not 5. "
United States
Andrea
The price is HK$1,187
HK$1,359 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Gem Museum Suites
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 Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"I had a great stay at this hotel. It was centrally located around so many things, the staff was incredibly friendly, and the room was exceptionally clean. I really enjoyed my stay and would definitely stay here again! The breakfast food at their restaurant was amazing as well! "
Cierra 1-night trip
Posted 22 hours ago
The Royal Sonesta Chicago Downtown