Search Holiday Rentals in Central Chicago

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sep - 7 Sep

Top Holiday Rentals in Central Chicago

Our top choices for Central Chicago holiday rentals

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (893)
"great food spots all around and beautiful sites to see "
The price is 3.778.857 ₫
5.208.325 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (481)
"It was a great property to stay at, definitely would book again! "
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (344)
"A lot of good food options walkable distance. "
The price is 5.446.920 ₫
6.981.290 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Level Chicago – Old Town
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (633)
"Loved this apartment style stay near everything we wanted to visit in Chicago. "
The price is 3.393.474 ₫
3.983.781 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Kasa South Loop Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (331)
"Great stay"
Kasa South Loop Chicago
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (177)
"Great location!!!"
The price is 3.919.594 ₫
4.601.211 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (47)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is 3.919.594 ₫
4.601.446 ₫ total
includes taxes & fees
3 Sept - 4 Sept
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
Business centre

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (165)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (132)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is 4.182.654 ₫
4.910.016 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Central Chicago Hotel Reviews

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"Wonderful, close to all the great areas to enjoy Chicago "
clifton 3-night trip
Posted 1 day ago
citizenM Chicago Downtown