Search Cheap Flights to
Countryside

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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.

Spirit Airlines
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
Select Spirit Airlines flight, departing Tue, Jul 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $75 found 1 hour ago
Frontier Airlines
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
Select Frontier Airlines flight, departing Tue, Jul 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jul 23, priced at $92 found 19 hours ago
Frontier Airlines
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
Select Frontier Airlines flight, departing Tue, Jul 15 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Jul 23, priced at $92 found 5 days ago
Spirit Airlines
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
Select Spirit Airlines flight, departing Wed, Jul 30 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $100 found 19 hours ago
Spirit Airlines
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
Select Spirit Airlines flight, departing Tue, Aug 26 from Los Angeles Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $130 found 10 hours ago
United
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
Select United flight, departing Sat, Aug 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $132 found 1 hour ago
Delta
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
Select Delta flight, departing Sat, Aug 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $132 found 1 hour ago
American Airlines
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
Select American Airlines flight, departing Sat, Aug 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $132 found 1 hour ago
Frontier Airlines
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
Select Frontier Airlines flight, departing Tue, Aug 12 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Aug 13, priced at $151 found 19 hours ago
Contour Airlines
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
Select Contour Airlines flight, departing Mon, Sep 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $189 found 19 hours ago
Delta
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
Select Delta flight, departing Tue, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 9, priced at $191 found 1 hour ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 19 hours ago
$197
Roundtrip
found 19 hours ago
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 found 19 hours ago
Alaska Airlines
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
Select Alaska Airlines flight, departing Tue, Oct 14 from Los Angeles Intl. to O'Hare Intl., returning Tue, Oct 28, priced at $216 found 19 hours ago
Delta
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
Select Delta flight, departing Mon, Aug 11 from Los Angeles Intl. to Midway Intl., returning Tue, Aug 12, priced at $255 found 19 hours ago
JetBlue Airways
Wed, Oct 15 - Wed, Oct 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$273 Roundtrip, just found
$273
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Oct 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 22, priced at $273 just found
KEY LIME AIR DBA DENVER AIR CONNECTION
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
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Dec 23 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 30, priced at $325 found 19 hours ago
Countryside Flight Information
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
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
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

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InterContinental Chicago Magnificent Mile by IHG
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
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

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Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
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

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Hilton Chicago/Magnificent Mile Suites
Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
4 out of 5
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

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Hilton Chicago O'Hare Airport
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
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

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Embassy Suites by Hilton Chicago Downtown River North
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
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

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citizenM Chicago Downtown
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection
3.5 out of 5
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

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The Whitehall Hotel, BW Premier Collection
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
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

Get rates
Hotel Felix River North/Magnificent Mile
See all 4,786 properties in Countryside
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
Holiday Inn Chicago SW-Countryside ConfCtr by IHG
3.5 out of 5
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

Get rates
Holiday Inn Chicago SW-Countryside ConfCtr by IHG
See all 4,786 properties in Countryside
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.