Search Cheap Flights to
Countryside

Photo by Monica Ferro

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Countryside Flights as Low as $90

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Thu, Nov 6 - Fri, Nov 7
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$90 Roundtrip, found 3 days ago
$90
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Nov 6 from Charlotte-Douglas Intl. to O'Hare Intl., returning Fri, Nov 7, priced at $90 found 3 days ago
Frontier Airlines
Mon, Sep 29 - Mon, Oct 6
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$92 Roundtrip, found 5 days ago
$92
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Sep 29 from Charlotte-Douglas Intl. to O'Hare Intl., returning Mon, Oct 6, priced at $92 found 5 days ago
Frontier Airlines
Mon, Sep 15 - Thu, Sep 18
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$96 Roundtrip, found 2 days ago
$96
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Sep 15 from Charlotte-Douglas Intl. to O'Hare Intl., returning Thu, Sep 18, priced at $96 found 2 days ago
Frontier Airlines
Sun, Sep 14 - Thu, Sep 18
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$96 Roundtrip, found 2 days ago
$96
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Sep 14 from Charlotte-Douglas Intl. to O'Hare Intl., returning Thu, Sep 18, priced at $96 found 2 days ago
Frontier Airlines
Thu, Sep 11 - Thu, Sep 18
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Sep 11 from Charlotte-Douglas Intl. to O'Hare Intl., returning Thu, Sep 18, priced at $98 found 2 days ago
Frontier Airlines
Sun, Sep 14 - Mon, Sep 15
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 2 days ago
$102
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Sep 14 from Charlotte-Douglas Intl. to O'Hare Intl., returning Mon, Sep 15, priced at $102 found 2 days ago
Frontier Airlines
Mon, Sep 29 - Fri, Oct 10
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$104 Roundtrip, found 5 days ago
$104
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Sep 29 from Charlotte-Douglas Intl. to O'Hare Intl., returning Fri, Oct 10, priced at $104 found 5 days ago
Frontier Airlines
Thu, Sep 11 - Mon, Sep 15
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$104 Roundtrip, found 2 days ago
$104
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Sep 11 from Charlotte-Douglas Intl. to O'Hare Intl., returning Mon, Sep 15, priced at $104 found 2 days ago
Frontier Airlines
Sun, Nov 9 - Mon, Nov 10
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 3 days ago
$108
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Nov 9 from Charlotte-Douglas Intl. to O'Hare Intl., returning Mon, Nov 10, priced at $108 found 3 days ago
Frontier Airlines
Mon, Sep 29 - Thu, Oct 9
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 5 days ago
$110
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Sep 29 from Charlotte-Douglas Intl. to O'Hare Intl., returning Thu, Oct 9, priced at $110 found 5 days ago
Frontier Airlines
Fri, Nov 7 - Mon, Nov 10
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 3 days ago
$117
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Nov 7 from Charlotte-Douglas Intl. to O'Hare Intl., returning Mon, Nov 10, priced at $117 found 3 days ago
Spirit Airlines
Fri, Sep 5 - Mon, Sep 8
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Fri, Sep 5 from Charlotte-Douglas Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $167 found 3 days ago
Bargain Flight
Sun, Sep 7 - Tue, Sep 9
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$173 Roundtrip, found 11 hours ago
$173
Roundtrip
found 11 hours ago
Select Bargain Flight flight, departing Sun, Sep 7 from Charlotte-Douglas Intl. to O'Hare Intl., returning Tue, Sep 9, priced at $173 found 11 hours ago
Delta
Sat, Nov 8 - Sat, Nov 8
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$191 Roundtrip, found 3 days ago
$191
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Nov 8 from Charlotte-Douglas Intl. to O'Hare Intl., returning Sat, Nov 8, priced at $191 found 3 days ago
Frontier Airlines
Thu, Nov 27 - Thu, Dec 4
CLT
Charlotte-Douglas Intl.
MDW
Midway Intl.
$208 Roundtrip, found 2 days ago
$208
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Nov 27 from Charlotte-Douglas Intl. to Midway Intl., returning Thu, Dec 4, priced at $208 found 2 days ago
American Airlines
Thu, Nov 20 - Mon, Nov 24
CLT
Charlotte-Douglas Intl.
RFD
Greater Rockford
$316 Roundtrip, found 6 days ago
$316
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Nov 20 from Charlotte-Douglas Intl. to Greater Rockford, returning Mon, Nov 24, priced at $316 found 6 days ago

Cheap Flights to Countryside

Fall in love at first flight with your vacation to Countryside by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Countryside on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Countryside, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Countryside

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Countryside with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Countryside?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Countryside are in November, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Countryside?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Countryside.

What airport is best to fly into Countryside?

When you’re planning your trip to Countryside, convenience is the name of the game. Luckily, Countryside Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Countryside must-do list.

How much are flights to Countryside?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Countryside on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $90, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Countryside?

The trick to saving a stack of cash on your flight to Countryside? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $90 right now, why wait?

Countryside Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$66

Last Minute Hotel Deals in Countryside

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on Aug 20, 2025

Get rates
The Wade
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! (8,965 reviews)
"Family had a great stay."

Reviewed on Aug 21, 2025

Get rates
Congress Plaza Hotel
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! (4,749 reviews)
"Very nice location. Close to redline (2 min walk) close to a lot of restaurants and convenient stores"

Reviewed on Aug 22, 2025

Get rates
Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,885 reviews)
"Beautiful unique hotel, friendly staff and quiet for people who need to rest!"

Reviewed on Aug 21, 2025

Get rates
Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (3,728 reviews)
"Stress"

Reviewed on Aug 21, 2025

Get rates
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,239 reviews)
"I loved how nice the hotel staff was."

Reviewed on Aug 21, 2025

Get rates
Freehand Chicago
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! (2,669 reviews)
"What i liked was its location. In the middle of everything. But off the busy street. Restaurants & shopping a block away. What needs to be done is an upgrade to the bathroom. Wasn't bad , but tub/shower area need some attention."

Reviewed on Aug 20, 2025

Get rates
Hilton Chicago/Magnificent Mile Suites
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! (3,614 reviews)
"Very clean and up to date location. Staff was very nice and check was smooth and easy"

Reviewed on Aug 21, 2025

Get rates
citizenM Chicago Downtown
See all 4,973 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! (1,097 reviews)
"The room was damp with a filthy rug. Shower leaked onto floor with shower door closed. Room was dated and uninviting. If I could have changed the reservation without losing money, I would have walked. Pass next time in town."

Reviewed on Aug 20, 2025

Get rates
Holiday Inn Chicago SW-Countryside ConfCtr by IHG
See all 4,973 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.