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Countryside

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Countryside Flights as Low as $124

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

Frontier Airlines
Sat, Sep 5 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$124 Roundtrip, found 1 hour ago
$124
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 9, priced at $124 found 1 hour ago
Frontier Airlines
Sat, Sep 5 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$127 Roundtrip, just found
$127
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $127 just found
Frontier Airlines
Thu, Oct 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 1 hour ago
$138
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Oct 15 from Los Angeles Intl. to O'Hare Intl., returning Mon, Oct 19, priced at $138 found 1 hour ago
Frontier Airlines
Sun, Sep 6 - Thu, Sep 10
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$170 Roundtrip, found 1 hour ago
$170
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Sep 6 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Sep 10, priced at $170 found 1 hour ago
Bargain Flight
Sun, Sep 6 - Tue, Sep 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 3 hours ago
$172
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Sun, Sep 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $172 found 3 hours ago
Frontier Airlines
Thu, Sep 10 - Sat, Sep 12
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$198 Roundtrip, found 1 hour ago
$198
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Sep 10 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Sep 12, priced at $198 found 1 hour ago
Bargain Flight
Sun, May 23 - Fri, May 28
PIT
Pittsburgh Intl.
ORD
O'Hare Intl.
$199 Roundtrip, found 11 hours ago
$199
Roundtrip
found 11 hours ago
Select Bargain Flight flight, departing Sun, May 23 from Pittsburgh Intl. to O'Hare Intl., returning Fri, May 28, priced at $199 found 11 hours ago
Delta
Fri, Nov 6 - Mon, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Select Delta flight, departing Fri, Nov 6 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 16, priced at $217 just found
American Airlines
Fri, Nov 6 - Mon, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Select American Airlines flight, departing Fri, Nov 6 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 16, priced at $217 just found
Southwest Airlines
Tue, Sep 22 - Tue, Sep 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$241 Roundtrip, found 11 hours ago
$241
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Tue, Sep 22 from Los Angeles Intl. to Midway Intl., returning Tue, Sep 29, priced at $241 found 11 hours ago
American Airlines
Wed, Sep 2 - Wed, Sep 16
LAX
Los Angeles Intl.
RFD
Greater Rockford
$300 Roundtrip, found 3 days ago
$300
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Greater Rockford, returning Wed, Sep 16, priced at $300 found 3 days ago
American Airlines
Tue, Sep 8 - Fri, Sep 18
PIT
Pittsburgh Intl.
RFD
Greater Rockford
$330 Roundtrip, found 5 days ago
$330
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Sep 8 from Pittsburgh Intl. to Greater Rockford, returning Fri, Sep 18, priced at $330 found 5 days ago
Alaska Airlines
Fri, Nov 6 - Mon, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$337 Roundtrip, just found
$337
Roundtrip
just found
Select Alaska Airlines flight, departing Fri, Nov 6 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 16, priced at $337 just found
American Airlines
Thu, Sep 10 - Sat, Sep 12
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$354 Roundtrip, found 5 hours ago
$354
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Thu, Sep 10 from Dallas-Fort Worth Intl. to Greater Rockford, returning Sat, Sep 12, priced at $354 found 5 hours ago
JetBlue Airways
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$363 Roundtrip, found 1 hour ago
$363
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $363 found 1 hour ago
American Airlines
Fri, Sep 11 - Sun, Sep 13
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$367 Roundtrip, found 2 days ago
$367
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Sep 11 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sun, Sep 13, priced at $367 found 2 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 September, 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 14 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 $124, 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 $124 right now, why wait?

Countryside Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$123

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
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! (2,125 reviews)
"Staff were amazing! Extremely helpful and accommodating, let us check in about 5 hours early. Definitely recommend"

Reviewed on Aug 29, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (880 reviews)
"Check in can be slightly confusing however you get the hang of it quickly. It was close to many amenities, a train away or a longer walk. The loft was cleaning than most however there was still dust and some crumbs left behind. Over all we were pleased with our stay even though very pricey for 3 ..."

Reviewed on Aug 29, 2026

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Kasa Magnificent Mile Chicago
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
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Hampton Inn Chicago Downtown/Magnificent Mile
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 ...
8.6/10 Excellent! (3,102 reviews)
"The hotel was exceptionally beautifully and the staff were so friendly and helpful. We were there for the BTS concert and the hotel went out of their way to make the space welcoming to Army (fans) by setting up a designated spot for photo ops and meet ups! They also played BTS music in the lobby ..."

Reviewed on Aug 30, 2026

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Hilton Chicago
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 ...
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Hyatt Regency Chicago
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 ...
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River Hotel
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
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The Allegro Royal Sonesta Hotel Chicago Loop
See all 4,837 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! (1,630 reviews)
"Staff was wonderful!"

Reviewed on Aug 29, 2026

Get rates
William Tell Hotel MOD Collection by Sonesta
See all 4,837 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.