A city skyline at dusk with illuminated buildings reflecting on the water.

Central Chicago Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Central Chicago holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,219 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
The price is RM619
RM847 total
includes taxes & fees
18 Aug - 19 Aug
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (503 reviews)
"Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place."
United States
Serigne abdou
The price is RM1,209
RM1,520 total
includes taxes & fees
20 Aug - 21 Aug
Level Chicago – Old Town
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.8 out of 10, Excellent, (43 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is RM947
RM1,112 total
includes taxes & fees
22 Jul - 23 Jul
Wrigleyville Suites
Breakfast, lunch and dinner served

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.6 out of 10, Exceptional, (165 reviews)
"Love this place. Excellent free breakfast. Friendly staff. Cute rooms :) Would highly recommend and would stay again :)"
United States
Ines
The price is RM605
RM692 total
includes taxes & fees
20 Aug - 21 Aug
The Gem Museum Suites
Lounge

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (11 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is RM987
RM1,584 total
includes taxes & fees
21 Jul - 22 Jul
At Home in Oak Park
Lounge

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is RM879
RM1,461 total
includes taxes & fees
17 Aug - 18 Aug
Historic Oak Park Home
Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is RM744
RM1,307 total
includes taxes & fees
3 Aug - 4 Aug
The Oak Park Loft
Exterior

Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is RM1,135
RM1,754 total
includes taxes & fees
27 Jul - 28 Jul
Historic Oak Park Residence
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.
View all properties
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

8/10 Good
"Hotel room was nice, not very big but still had everything that was needed. AC worked just fine as well. The area was great, lots of things around. The subway is about a 4 minute walk which makes using public transportation a lot easier. Most tourist areas are about a 20 minute walk from this place!"
Jocelyn 4-night trip
Posted less than an hour ago
Eurostars Magnificent Mile

Find out more about Central Chicago

Search for holiday rentals in Central Chicago on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Central Chicago using one of the methods below:

  • View our selection of featured holiday rentals in Central Chicago
  • Use the map to find apartments and other holiday homes in the Central Chicago neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Central Chicago while they last

Look no further and take a look at our great range of rental properties in Central Chicago!

Explore a world of travel with Expedia