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Countryside

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Countryside Flights as Low as $130

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

Frontier Airlines
Wed, Nov 11 - Wed, Nov 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 3 days ago
$130
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Nov 11 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $130 found 3 days ago
Frontier Airlines
Thu, Nov 19 - Thu, Dec 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 5 days ago
$138
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Nov 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Dec 10, priced at $138 found 5 days ago
Frontier Airlines
Wed, Dec 2 - Sat, Dec 12
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$145 Roundtrip, found 3 days ago
$145
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Harry Reid Intl. to O'Hare Intl., returning Sat, Dec 12, priced at $145 found 3 days ago
Frontier Airlines
Sat, Nov 14 - Sat, Nov 14
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$166 Roundtrip, found 4 days ago
$166
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Nov 14 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, Nov 14, priced at $166 found 4 days ago
Bargain Flight
Thu, Nov 26 - Thu, Dec 17
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$169 Roundtrip, found 1 hour ago
$169
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Thu, Nov 26 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Dec 17, priced at $169 found 1 hour ago
Frontier Airlines
Sat, Oct 17 - Tue, Nov 3
MSY
Louis Armstrong New Orleans Intl.
ORD
O'Hare Intl.
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Oct 17 from Louis Armstrong New Orleans Intl. to O'Hare Intl., returning Tue, Nov 3, priced at $179 found 5 days ago
Frontier Airlines
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$184 Roundtrip, just found
$184
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $184 just found
Delta
Wed, Oct 14 - Tue, Nov 3
MSY
Louis Armstrong New Orleans Intl.
ORD
O'Hare Intl.
$208 Roundtrip, found 5 days ago
$208
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Oct 14 from Louis Armstrong New Orleans Intl. to O'Hare Intl., returning Tue, Nov 3, priced at $208 found 5 days ago
American Airlines
Wed, Nov 4 - Mon, Nov 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$220 Roundtrip, found 20 hours ago
$220
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Wed, Nov 4 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 9, priced at $220 found 20 hours ago
Southwest Airlines
Wed, Dec 2 - Tue, Dec 15
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$223 Roundtrip, found 23 hours ago
$223
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 15, priced at $223 found 23 hours ago
Southwest Airlines
Tue, Oct 13 - Wed, Oct 21
LAX
Los Angeles Intl.
MDW
Midway Intl.
$241 Roundtrip, found 23 hours ago
$241
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Tue, Oct 13 from Los Angeles Intl. to Midway Intl., returning Wed, Oct 21, priced at $241 found 23 hours ago
Frontier Airlines
Wed, Oct 28 - Tue, Nov 3
LAS
Harry Reid Intl.
MDW
Midway Intl.
$242 Roundtrip, found 22 hours ago
$242
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Wed, Oct 28 from Harry Reid Intl. to Midway Intl., returning Tue, Nov 3, priced at $242 found 22 hours ago
Alaska Airlines
Fri, Oct 16 - Thu, Oct 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, just found
$257
Roundtrip
just found
Select Alaska Airlines flight, departing Fri, Oct 16 from Los Angeles Intl. to O'Hare Intl., returning Thu, Oct 22, priced at $257 just found
Frontier Airlines
Thu, Nov 19 - Sat, Nov 21
MSY
Louis Armstrong New Orleans Intl.
MDW
Midway Intl.
$268 Roundtrip, found 15 hours ago
$268
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Thu, Nov 19 from Louis Armstrong New Orleans Intl. to Midway Intl., returning Sat, Nov 21, priced at $268 found 15 hours ago
JetBlue Airways
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$291 Roundtrip, found 8 hours ago
$291
Roundtrip
found 8 hours ago
Select JetBlue Airways flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $291 found 8 hours ago
Sun Country Airlines
Thu, Oct 29 - Sun, Nov 8
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$541 Roundtrip, found 5 days ago
$541
Roundtrip
found 5 days ago
Select Sun Country Airlines flight, departing Thu, Oct 29 from Harry Reid Intl. to O'Hare Intl., returning Sun, Nov 8, priced at $541 found 5 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 $130, 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 $130 right now, why wait?

Countryside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$137

Last Minute Hotel Deals in Countryside

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! (5,460 reviews)
"Great location , staff was helpful . Main lobby and lounge were nice, however the hotel rooms are very outdated."

Reviewed on Sep 22, 2026

Get rates
River Hotel
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! (2,302 reviews)
"The location was terrific. Access to amazing restaurants were walking distance. Easy travel to Convention Center of Lakeshore. The staff was wonderfully accommodating and friendly. Service was respectful, prompt and everyone had a welcoming smile. Parking adjacent to the hotel made it fast , easy ..."

Reviewed on Sep 22, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
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 ...
7.8/10 Good! (2,205 reviews)
"I don’t usually do this but I had to write a review, upon arrival the lady at the counter seem like she was pissed off, handed us the key and we got to our room everything was fine, until the second day there was a leak on the ceiling inside the restroom."

Reviewed on Sep 22, 2026

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The Chicago Hotel Collection - Magnificent Mile
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 ...
8/10 Very Good! (1,629 reviews)
"The hotel needs remodeling, but it was truly a wonderful stay. We had a comfortable bed, an air conditioned room, and the most helpful staff. It would have been nice to have more updated elevators, and for the breakfast to be with real plates, cups, and utensils. But otherwise, we really enjoyed ..."

Reviewed on Sep 22, 2026

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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! (3,278 reviews)
"Rooms are large and very clean. Has a refrigerator, but no microwave."

Reviewed on Sep 22, 2026

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Hilton Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
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Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
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
See all 4,873 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! (1,662 reviews)
"My only complaint were the beds. Idk what kind they were cause my friend when we got in sat down on hers and it made crunching noises and went down like it was broke. Beds were awful. Not comfortable at all. The shower head was all messed up and spaying everywhere cause it was broke. And the door ..."

Reviewed on Sep 22, 2026

Get rates
William Tell Hotel MOD Collection by Sonesta
See all 4,873 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.