Search Cheap Flights toCountryside
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Countryside Flights as Low as $75
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Jul 22 - Tue, Jul 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$75 Roundtrip, found 1 hour ago
$75
Roundtrip
found 1 hour ago

Tue, Jul 22 - Wed, Jul 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$92 Roundtrip, found 19 hours ago
$92
Roundtrip
found 19 hours ago

Tue, Jul 15 - Wed, Jul 23
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$92 Roundtrip, found 5 days ago
$92
Roundtrip
found 5 days ago

Wed, Jul 30 - Wed, Aug 6
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 19 hours ago
$100
Roundtrip
found 19 hours ago

Tue, Aug 26 - Sat, Aug 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 10 hours ago
$130
Roundtrip
found 10 hours ago

Sat, Aug 16 - Sat, Aug 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 1 hour ago
$132
Roundtrip
found 1 hour ago

Sat, Aug 16 - Sat, Aug 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 1 hour ago
$132
Roundtrip
found 1 hour ago

Sat, Aug 16 - Sat, Aug 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 1 hour ago
$132
Roundtrip
found 1 hour ago

Tue, Aug 12 - Wed, Aug 13
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$151 Roundtrip, found 19 hours ago
$151
Roundtrip
found 19 hours ago

Mon, Sep 8 - Thu, Sep 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 19 hours ago
$189
Roundtrip
found 19 hours ago

Tue, Sep 9 - Tue, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, found 1 hour ago
$191
Roundtrip
found 1 hour ago

Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 19 hours ago
$197
Roundtrip
found 19 hours ago

Tue, Oct 14 - Tue, Oct 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 19 hours ago
$216
Roundtrip
found 19 hours ago

Mon, Aug 11 - Tue, Aug 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$255 Roundtrip, found 19 hours ago
$255
Roundtrip
found 19 hours ago

Wed, Oct 15 - Wed, Oct 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$273 Roundtrip, just found
$273
Roundtrip
just found

Tue, Dec 23 - Tue, Dec 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$325 Roundtrip, found 19 hours ago
$325
Roundtrip
found 19 hours ago
Destination airport | O'Hare Intl. |
Destination airport IATA code | ORD |
Roundtrip price | $75 |
Last Minute Hotel Deals in Countryside

InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (1,970 reviews)
"Even after renovation rooms are still looking dated"
Reviewed on Jul 4, 2025

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,872 reviews)
"The history of the hotel is amazing and she might be an old girl with old features but she still shines like a diamond. Plus, the lake side view cannot be beat."
Reviewed on Jul 4, 2025

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,397 reviews)
"Staff was amazing, and rooms were clean and comfortable! Overall a great stay"
Reviewed on Jul 6, 2025

Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8/10 Very Good! (2,049 reviews)
"Convenient to airport after flight got cancelled not once but twice ."
Reviewed on Jul 2, 2025

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,357 reviews)
"The location is very convenient, close to the train and easy to get to most attractions. The rokms are spacious and clean. The breakfast and happy hour are very good and a nice convenience."
Reviewed on Jul 5, 2025

citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (3,284 reviews)
"Very nice stay. Looking forward to be back."
Reviewed on Jul 5, 2025

The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl, Chicago, IL
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
8.2/10 Very Good! (3,472 reviews)
"Nice location . Older decor but room was nice and clean You have to call for ice , so I did and they never brought it . Breakfast i wish was different day to day , pretty much the same thing daily ."
Reviewed on Jul 7, 2025

Hotel Felix River North/Magnificent Mile
111 W Huron St, Chicago, IL
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (1,835 reviews)
"I like that it was so close to the nightlife."
Reviewed on Jul 6, 2025
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.
Top Hotels With Free Airport Shuttle

Holiday Inn Chicago SW-Countryside ConfCtr by IHG
6201 Joliet Rd, Countryside, IL
Stay at this 3.5-star business-friendly hotel in Countryside. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the clean rooms ...
7.8/10 Good! (1,003 reviews)
"Service was amazing can’t wait to see how the pool looks after renovations are done! Rooms were nice and everything was clean!"
Reviewed on Jul 5, 2025
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 Hotels
- InterContinental Chicago Magnificent Mile by IHG
- Congress Plaza Hotel
- Hilton Chicago/Magnificent Mile Suites
- Hilton Chicago O'Hare Airport
- Embassy Suites by Hilton Chicago Downtown River North
- The Whitehall Hotel, BW Premier Collection
- Hotel Felix River North/Magnificent Mile
- Swissotel - Chicago
- Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
- The Royal Sonesta Chicago Downtown
- Crowne Plaza Chicago West Loop by IHG
- River Hotel
- Freehand Chicago
- The Westin Michigan Avenue Chicago
- Fairmont Chicago at Millennium Park