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Countryside

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Countryside Flights as Low as $70

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

Frontier Airlines
Tue, May 12 - Tue, May 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$70 Roundtrip, found 1 day ago
$70
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 12 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, May 19, priced at $70 found 1 day ago
Frontier Airlines
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, found 5 hours ago
$76
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $76 found 5 hours ago
Frontier Airlines
Thu, Apr 30 - Thu, May 7
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$161 Roundtrip, found 5 days ago
$161
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, May 7, priced at $161 found 5 days ago
Frontier Airlines
Mon, Apr 27 - Thu, Apr 30
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$164 Roundtrip, found 22 hours ago
$164
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Mon, Apr 27 from Charlotte-Douglas Intl. to O'Hare Intl., returning Thu, Apr 30, priced at $164 found 22 hours ago
Bargain Flight
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $165 found 1 day ago
Bargain Flight
Wed, May 6 - Sat, May 30
BNA
Nashville Intl.
ORD
O'Hare Intl.
$175 Roundtrip, found 11 hours ago
$175
Roundtrip
found 11 hours ago
Select Bargain Flight flight, departing Wed, May 6 from Nashville Intl. to O'Hare Intl., returning Sat, May 30, priced at $175 found 11 hours ago
Spirit Airlines
Sat, May 16 - Tue, May 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$178 Roundtrip, found 2 days ago
$178
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, May 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 19, priced at $178 found 2 days ago
Frontier Airlines
Tue, May 12 - Sat, May 30
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$185 Roundtrip, found 5 days ago
$185
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, May 12 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Sat, May 30, priced at $185 found 5 days ago
American Airlines
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 5 hours ago
$197
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $197 found 5 hours ago
Delta
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 5 hours ago
$197
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $197 found 5 hours ago
Contour Airlines
Wed, Jun 10 - Mon, Jun 22
BNA
Nashville Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 11 hours ago
$217
Roundtrip
found 11 hours ago
Select Contour Airlines flight, departing Wed, Jun 10 from Nashville Intl. to O'Hare Intl., returning Mon, Jun 22, priced at $217 found 11 hours ago
American Airlines
Tue, May 26 - Tue, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
RFD
Greater Rockford
$233 Roundtrip, found 2 days ago
$233
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, May 26 from Baltimore Washington Intl. Thurgood Marshall to Greater Rockford, returning Tue, Jun 2, priced at $233 found 2 days ago
American Airlines
Fri, May 15 - Mon, May 18
CLT
Charlotte-Douglas Intl.
RFD
Greater Rockford
$265 Roundtrip, found 4 days ago
$265
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, May 15 from Charlotte-Douglas Intl. to Greater Rockford, returning Mon, May 18, priced at $265 found 4 days ago
Delta
Tue, Sep 8 - Tue, Sep 15
CLT
Charlotte-Douglas Intl.
MDW
Midway Intl.
$279 Roundtrip, found 5 hours ago
$279
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Sep 8 from Charlotte-Douglas Intl. to Midway Intl., returning Tue, Sep 15, priced at $279 found 5 hours ago
American Airlines
Thu, May 14 - Mon, May 18
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$304 Roundtrip, found 1 day ago
$304
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, May 14 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Mon, May 18, priced at $304 found 1 day ago
American Airlines
Wed, May 6 - Sat, May 30
BNA
Nashville Intl.
RFD
Greater Rockford
$467 Roundtrip, found 11 hours ago
$467
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, May 6 from Nashville Intl. to Greater Rockford, returning Sat, May 30, priced at $467 found 11 hours 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 May, 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 $70, 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 $70 right now, why wait?

Countryside Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$70

Last Minute Hotel Deals in Countryside

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (2,640 reviews)
Good location

Reviewed on Apr 26, 2026

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Hotel Felix River North/Magnificent Mile
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! (5,129 reviews)
The only downside is the elevator waiting time for higher floor. But the staff was super friendly!

Reviewed on Apr 26, 2026

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River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (3,461 reviews)
Friendly helpful staff. Room larger than expected. Cold filtered water available by elevator. Great location.

Reviewed on Apr 26, 2026

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Club Quarters Hotel, Central Loop, 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 ...
9/10 Wonderful! (4,193 reviews)
Our room ( 2 queens) had an adjoining room with doors separating it from bedroom. Very nice to have more space.

Reviewed on Apr 25, 2026

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Hilton Chicago/Magnificent Mile Suites
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (3,960 reviews)
It was great property, amazing location and the breakfast was fantastic.

Reviewed on Apr 25, 2026

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Hotel Riu Plaza Chicago
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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Holiday Inn Chicago Dwtn - The Mart 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 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,140 reviews)
We have always loved staying at the Congress over the past few years. This was the first time we were disappointed. We asked for our 2 rooms to be close together but we were on opposite ends of the same floor. Our room was hot and the in unit air conditioner barely worked. Maintenance was sent to ...

Reviewed on Apr 25, 2026

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Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,411 reviews)
Very nice hotel

Reviewed on Apr 25, 2026

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Palmer House a Hilton Hotel
See all 5,058 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! (1,459 reviews)
Calvin at the front desk was extremely friendly and helpful. I appreciate his attention to detail and recommendations.

Reviewed on Apr 21, 2026

Get rates
William Tell Hotel MOD Collection by Sonesta
See all 5,058 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.