Photo by Monica Ferro

Countryside Holiday Rentals

    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
12 Jun - 13 Jun
Tomorrow
13 Jun - 14 Jun
This weekend
13 Jun - 15 Jun
Next weekend
20 Jun - 22 Jun

Holiday Rentals in Countryside

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (783)
"we enjoyed the stay"
The price is S$280
includes taxes & fees
29 Jun - 30 Jun
Sentral Michigan Avenue
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, (530)
" The check in process was smooth and easy. Good location, walkable to many places. This was our 4th stay and we will be back!!!!"
The price is S$214
includes taxes & fees
29 Jun - 30 Jun
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Living room

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.6 out of 10, Excellent, (301)
"Super cool spot in a great part of the city."
The price is S$191
includes taxes & fees
2 Jul - 3 Jul
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (320)
"Hotel was nice"
The price is S$488
includes taxes & fees
15 Jun - 16 Jun
Level Chicago – Old Town
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, (420)
"Great stay "
Kasa Magnificent Mile Chicago
Sonder by Marriott Bonvoy The Burnham Apartments Loop
1 bedroom, premium bedding, individually decorated

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (182)
"Good size room, clean and open."
The price is S$281
includes taxes & fees
29 Jun - 30 Jun
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Full-sized fridge, microwave, oven, stovetop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.4 out of 10, Very good, (106)
"We love staying at Sonder properties. The apartment has a full kitchen with everything you need, the shower is so refreshing, and the in-room washer/dryer is super handy when traveling."
The price is S$165
includes taxes & fees
30 Jun - 1 Jul
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (165)
"Great room, well decorated and appointed. Great location!"
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
View from property

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.4 out of 10, Very good, (162)
"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "
The price is S$229
includes taxes & fees
1 Jul - 2 Jul
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Kasa South Loop Chicago
City view

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (302)
"Nice place to stay"
Kasa South Loop Chicago
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
1 bedroom, desk, laptop workspace, blackout curtains

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

2.5 star property
3.6 out of 10, (35)
"Nice inside room but it’s not safe outside area"
The price is S$121
includes taxes & fees
25 Jun - 26 Jun
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Sonder by Marriott Bonvoy The Opal Apartments River North
42-inch flat-screen TV with digital channels, TV, streaming services

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.8 out of 10, Excellent, (39)
"This is a perfect location to walk around downtown, have dining options at walking distance. Everything was perfect for my family trip. The only issue is the noise its close to walgreens that gets deliveries at like 5am and the noise is so bad it wakes you up."
The price is S$191
includes taxes & fees
29 Jun - 30 Jun
Sonder by Marriott Bonvoy The Opal Apartments River North
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
8.8 out of 10, Excellent, (5)
The price is S$403
includes taxes & fees
14 Jun - 15 Jun
Wrigleyville Suites
Kasa River North Chicago
Library

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (149)
"Great stay, clean room!"
Kasa River North Chicago
Sonder by Marriott Bonvoy Greektown Apartments
40-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.8 out of 10, Excellent, (53)
"Great location, easy stay!"
The price is S$281
includes taxes & fees
29 Jun - 30 Jun
Sonder by Marriott Bonvoy Greektown Apartments
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.6 out of 10, Exceptional, (14)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is S$274
includes taxes & fees
6 Jul - 7 Jul
Ground Floor Studios in 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 Galloping Ghost, or get out into nature at a spot like Grant Park. In the wider area, you’ll find popular places such as Soldier Field and Michigan Avenue.

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.