Search Cheap Flights to
Countryside

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Countryside Flights as Low as $93

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

Frontier Airlines
Tue, Oct 27 - Sat, Oct 31
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$93 Roundtrip, found 5 days ago
$93
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Oct 27 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, Oct 31, priced at $93 found 5 days ago
Frontier Airlines
Sun, Dec 6 - Mon, Dec 7
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 6 days ago
$100
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, Dec 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Dec 7, priced at $100 found 6 days ago
Frontier Airlines
Tue, Nov 24 - Mon, Dec 7
TPA
Tampa Intl.
ORD
O'Hare Intl.
$128 Roundtrip, found 6 days ago
$128
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Nov 24 from Tampa Intl. to O'Hare Intl., returning Mon, Dec 7, priced at $128 found 6 days ago
Frontier Airlines
Tue, Nov 17 - Thu, Nov 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$165 Roundtrip, found 7 hours ago
$165
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Los Angeles Intl. to O'Hare Intl., returning Thu, Nov 26, priced at $165 found 7 hours ago
Delta
Wed, Nov 4 - Mon, Nov 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Nov 4 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 9, priced at $169 found 2 days ago
Frontier Airlines
Fri, Nov 13 - Mon, Nov 16
TPA
Tampa Intl.
MDW
Midway Intl.
$175 Roundtrip, found 1 day ago
$175
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Nov 13 from Tampa Intl. to Midway Intl., returning Mon, Nov 16, priced at $175 found 1 day ago
Bargain Flight
Tue, Nov 3 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$181 Roundtrip, found 9 hours ago
$181
Roundtrip
found 9 hours ago
Select Bargain Flight flight, departing Tue, Nov 3 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Nov 19, priced at $181 found 9 hours ago
American Airlines
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 13 hours ago
$197
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $197 found 13 hours ago
Southwest Airlines
Wed, Dec 2 - Tue, Dec 15
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 15, priced at $197 found 2 days ago
Southwest Airlines
Sat, Nov 14 - Tue, Nov 17
LAX
Los Angeles Intl.
MDW
Midway Intl.
$237 Roundtrip, found 14 hours ago
$237
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Sat, Nov 14 from Los Angeles Intl. to Midway Intl., returning Tue, Nov 17, priced at $237 found 14 hours ago
Frontier Airlines
Thu, Nov 12 - Sun, Nov 15
ONT
Ontario Intl. Airport
ORD
O'Hare Intl.
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Nov 12 from Ontario Intl. Airport to O'Hare Intl., returning Sun, Nov 15, priced at $239 found 1 day ago
Delta
Thu, Nov 26 - Tue, Dec 8
ONT
Ontario Intl. Airport
MDW
Midway Intl.
$259 Roundtrip, found 1 day ago
$259
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Nov 26 from Ontario Intl. Airport to Midway Intl., returning Tue, Dec 8, priced at $259 found 1 day ago
JetBlue Airways
Sat, Nov 7 - Wed, Nov 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$291 Roundtrip, found 2 days ago
$291
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Nov 7 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $291 found 2 days ago
Alaska Airlines
Thu, Dec 10 - Mon, Dec 14
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$297 Roundtrip, found 2 hours ago
$297
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Thu, Dec 10 from Los Angeles Intl. to O'Hare Intl., returning Mon, Dec 14, priced at $297 found 2 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Dec 20 - Sat, Dec 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$459 Roundtrip, found 1 day ago
$459
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Dec 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 26, priced at $459 found 1 day ago
Sun Country Airlines
Wed, Nov 25 - Sat, Nov 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$873 Roundtrip, found 1 day ago
$873
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Wed, Nov 25 from Los Angeles Intl. to O'Hare Intl., returning Sat, Nov 28, priced at $873 found 1 day 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 October, 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 $93, 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 $93 right now, why wait?

Countryside Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$93

Last Minute Hotel Deals in Countryside

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 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Get rates
Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,529 reviews)
"Location couldn’t have been better. Heart of downtown. Front desk receptionist very helpful and kept our luggage until check-in. Have a nice coffee machine with free drinks on the second floor. However, found random hairs and hairpin in bathroom. Room is very basic and on the small side. Beds were ..."

Reviewed on Oct 16, 2026

Get rates
River Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (2,402 reviews)
"My sister and I went on a trip to Chicago for 3 days. Our stay was quite nice. Everythin went as planned. The price of the room with all the extras was exceptional. We are treated to a beautiful breakfast every morning. Each of us got a free drink each night and we got a dinner credit for each night. ..."

Reviewed on Oct 16, 2026

Get rates
The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (2,503 reviews)
"Room smelled so clean and fresh! Our room size was perfect for our stay. Staff was super nice and helped a lot. I did wish a microwave was available in the room. Location was great - nearby stores, cafes and a good bagel spot. Neighborhood was safe and secure. Would recommend the hotel for future ..."

Reviewed on Oct 16, 2026

Get rates
The Chicago Hotel Collection Ambassador Gold Coast
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (2,148 reviews)
"Loved this trendy hotel. Great location, amenities, and service."

Reviewed on Oct 16, 2026

Get rates
The Wade
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Get rates
Hilton Chicago
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Get rates
Eurostars Magnificent Mile
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Get rates
Hyatt Regency Chicago
See all 4,983 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

William Tell Hotel MOD Collection by Sonesta

William Tell Hotel MOD Collection by Sonesta

3.5 out of 5
6201 Joliet Rd Countryside IL
Book a stay at this business-friendly hotel in Countryside. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the clean ...
8/10 Very Good! (1,679 reviews)
"Staff was good room was great, the restaurant was closed the day we stayed there that was the only drawback"

Reviewed on Oct 13, 2026

Get rates
William Tell Hotel MOD Collection by Sonesta
See all 4,983 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.