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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Countryside holiday rentals

Indoor pool

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,095 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is 2.857.482 ₫
4.119.136 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (435 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town
Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms

Apartment in Oak Park

The Oak Park Loft
2.0 star property
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is 3.282.787 ₫
6.651.826 ₫ total
includes taxes & fees
2 Mar - 3 Mar
The Oak Park Loft
Lounge

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.4 out of 10, Exceptional, (184 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Comfort Double Room | Desk, laptop workspace, blackout curtains, free WiFi

Aparthotel in Harvey

Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
4.2 out of 10, (73 reviews)
"Under renovations so some rooms have missing appliances, even through an app they require a deposit. Utter wise nice room and workers"
United States
Destin
The price is 2.204.507 ₫
2.490.652 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Living area

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.2 out of 10, Wonderful, (29 reviews)
"Nice place "
United States
Barry
The price is 2.204.507 ₫
2.587.871 ₫ total
includes taxes & fees
3 Mar - 4 Mar
Wrigleyville Suites
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

Apartment in Oak Park

Historic Oak Park Home
2.0 star property
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
Historic Oak Park Home
Interior

Aparthotel in West Town

River West, Third Floor Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (17 reviews)
"Loved the space and location "
United States
Caroline
River West, Third Floor Chicago by 747 Lofts
Apartment, Private Bathroom | Lounge

Apartment in Oak Park

At Home in Oak Park
3.5 star property
9.4 out of 10, Exceptional, (9 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is 3.799.517 ₫
7.243.342 ₫ total
includes taxes & fees
2 Mar - 3 Mar
At Home in Oak Park
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

Apartment in Oak Park

Historic Oak Park Residence
2.0 star property
9.6 out of 10, Exceptional, (12 reviews)
"Absolutely awesome "
United States
Erik
Historic Oak Park Residence
Interior

Aparthotel in West Town

Chicago Third Floor Studio by 747 Lofts
2.0 star property
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
The price is 3.458.678 ₫
11.724.128 ₫ total
includes taxes & fees
15 Mar - 16 Mar
Chicago Third Floor Studio by 747 Lofts
Interior

Aparthotel in West Town

River West, Second Floor Chicago by 747 Lofts
2.0 star property
9.6 out of 10, Exceptional, (4 reviews)
"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 2.088.549 ₫
9.359.783 ₫ total
includes taxes & fees
8 Mar - 9 Mar
River West, Second Floor Chicago by 747 Lofts
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/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"The staff and space in the room was great! Location is outstanding!"
Erin 1-night trip
Posted 1 day ago
Hilton Chicago/Magnificent Mile Suites

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 Parkway Bank Park Entertainment District, 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 Navy Pier.

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.