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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Countryside holiday rentals

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1014)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is ฿3,711
฿5,278 total
includes taxes & fees
22 Dec - 23 Dec
Sentral Michigan Avenue
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, (402)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
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
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
7.4 out of 10, Good, (3)
"Definitely is a scam of some sort. Very sketchy highly do not recommend. "
United States
Devon
The price is ฿3,392
฿3,982 total
includes taxes & fees
22 Dec - 23 Dec
Chicago luxury home suites
Studio | Exterior
River West, Second Floor Chicago by 747 Lofts

Aparthotel in West Town

River West, Second Floor Chicago by 747 Lofts
2.0 star property
9.6 out of 10, Exceptional, (4)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveller
The price is ฿1,829
฿6,825 total
includes taxes & fees
23 Dec - 24 Dec
River West, Second Floor Chicago by 747 Lofts
Living area
Wrigleyville Suites

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is ฿3,675
฿4,314 total
includes taxes & fees
22 Dec - 23 Dec
Wrigleyville Suites
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior
Historic Oak Park Residence

Apartment in Oak Park

Historic Oak Park Residence
2.0 star property
9.6 out of 10, Exceptional, (12)
"Absolutely awesome "
United States
Erik
The price is ฿6,878
฿11,362 total
includes taxes & fees
22 Dec - 23 Dec
Historic Oak Park Residence
House (3 Bedrooms) | Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Cottage in Forest Park

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
The price is ฿4,962
฿12,955 total
includes taxes & fees
22 Dec - 23 Dec
Classic Forest Park Foursquare < 1 Mi to Blue Line
Comfort Double Room | Desk, laptop workspace, blackout curtains, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Aparthotel in Harvey

Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
4.0 out of 10, (68)
"Good "
United States
Abel
The price is ฿2,390
฿2,700 total
includes taxes & fees
22 Dec - 23 Dec
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Studio | Exterior
Cabin 105 by 747 Lofts

Aparthotel in West Town

Cabin 105 by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is ฿1,861
฿4,210 total
includes taxes & fees
30 Dec - 31 Dec
Cabin 105 by 747 Lofts
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
Chicago Second Floor Studio by 747 Lofts

Aparthotel in West Town

Chicago Second Floor Studio by 747 Lofts
2.0 star property
8.8 out of 10, Excellent, (13)
"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."
United States
Barbara
The price is ฿2,020
฿4,422 total
includes taxes & fees
28 Dec - 29 Dec
Chicago Second Floor Studio by 747 Lofts
Design Apartment, Private Bathroom (The Oak Park Loft) | View from property
The Oak Park Loft

Apartment in Oak Park

The Oak Park Loft
2.0 star property
10.0 out of 10, Exceptional, (5)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ฿6,106
฿10,477 total
includes taxes & fees
23 Dec - 24 Dec
The Oak Park Loft
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 Countryside Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Amazing experience! The rooms were spotless, comfortable, and thoughtfully maintained. All hotel amenities were clean, well-organized, and ready to use. The breakfast was excellent, with a great variety of options to choose from. What truly made this stay extraordinary was the outstanding service. Brad, Vicente, Cruz, Eric, Ruby, and the entire team went above and beyond to ensure a memorable experience. Their professionalism, kindness, and attention to detail were exceptional. Without a doubt, this was a unique and unforgettable stay — truly a hotel that exceeds five-star expectations. ❤️"
Luz Gilmarie Ortiz 3-night trip
Posted 1 day ago
Hilton Chicago

Find out more about Countryside

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

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

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

Frequently asked questions

Can I find holiday rentals in Countryside?

Yes, there are holiday rentals close to the most popular sights in Countryside, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Countryside. Make sure you have time to check out the live music and zoo during your trip.

What can I see and do in Countryside?

Explore the area and family-friendly sights such as Childrens Museum of Oak Lawn, or get out into nature at a spot like Grant Park. In the wider area, you’ll find popular places such as Michigan Avenue and Wrigley Field.

What are holiday rentals like in Countryside?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Countryside. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for small groups.