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 $89

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

Frontier Airlines
Wed, Sep 16 - Mon, Sep 28
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$89 Roundtrip, found 3 days ago
$89
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Sep 28, priced at $89 found 3 days ago
Frontier Airlines
Tue, Aug 25 - Wed, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$98 Roundtrip, found 3 days ago
$98
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Aug 25 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Aug 26, priced at $98 found 3 days ago
Frontier Airlines
Tue, Jul 7 - Tue, Jul 21
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$110 Roundtrip, found 3 days ago
$110
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Jul 7 from George Bush Intercontinental to O'Hare Intl., returning Tue, Jul 21, priced at $110 found 3 days ago
Frontier Airlines
Fri, Aug 28 - Thu, Sep 3
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 5 days ago
$124
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Aug 28 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Thu, Sep 3, priced at $124 found 5 days ago
United
Wed, Aug 19 - Wed, Aug 26
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 4 hours ago
$171
Roundtrip
found 4 hours ago
Select United flight, departing Wed, Aug 19 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Wed, Aug 26, priced at $171 found 4 hours ago
American Airlines
Wed, Aug 19 - Wed, Aug 26
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 4 hours ago
$171
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Aug 19 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Wed, Aug 26, priced at $171 found 4 hours ago
Frontier Airlines
Tue, Jul 28 - Thu, Jul 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$176 Roundtrip, found 3 hours ago
$176
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, Jul 28 from Los Angeles Intl. to O'Hare Intl., returning Thu, Jul 30, priced at $176 found 3 hours ago
JetBlue Airways
Wed, Sep 9 - Tue, Sep 15
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 9 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Tue, Sep 15, priced at $189 found 1 day ago
Delta
Tue, Sep 15 - Tue, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 19 hours ago
$197
Roundtrip
found 19 hours ago
Select Delta flight, departing Tue, Sep 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $197 found 19 hours ago
Delta
Wed, Aug 5 - Tue, Aug 18
IAH
George Bush Intercontinental
MDW
Midway Intl.
$209 Roundtrip, found 18 hours ago
$209
Roundtrip
found 18 hours ago
Select Delta flight, departing Wed, Aug 5 from George Bush Intercontinental to Midway Intl., returning Tue, Aug 18, priced at $209 found 18 hours ago
Delta
Tue, Sep 1 - Tue, Sep 8
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 1 from Fort Lauderdale - Hollywood Intl. to Midway Intl., returning Tue, Sep 8, priced at $217 found 2 days ago
Delta
Wed, Jul 22 - Wed, Jul 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$239 Roundtrip, found 2 days ago
$239
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jul 22 from Los Angeles Intl. to Midway Intl., returning Wed, Jul 29, priced at $239 found 2 days ago
Alaska Airlines
Tue, Oct 20 - Tue, Oct 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$271 Roundtrip, found 22 hours ago
$271
Roundtrip
found 22 hours ago
Select Alaska Airlines flight, departing Tue, Oct 20 from Los Angeles Intl. to O'Hare Intl., returning Tue, Oct 27, priced at $271 found 22 hours ago
American Airlines
Tue, Jun 23 - Sat, Jun 27
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$276 Roundtrip, found 2 days ago
$276
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jun 23 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sat, Jun 27, priced at $276 found 2 days ago
American Airlines
Fri, May 29 - Sat, Aug 1
IAH
George Bush Intercontinental
RFD
Greater Rockford
$329 Roundtrip, found 2 days ago
$329
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, May 29 from George Bush Intercontinental to Greater Rockford, returning Sat, Aug 1, priced at $329 found 2 days ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$418 Roundtrip, found 2 days ago
$418
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $418 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 16 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 $89, 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 $89 right now, why wait?

Countryside Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$137

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 ...
8/10 Very Good! (10,130 reviews)
"As one of my first solo trips, I was glad to feel very safe and comfortable during my stay. I had requested and paid extra for a lake front room. On the fourth floor I could barely see the lake, but did face the park. Good news and bad news because the street noise was very loud at times. I ate in ..."

Reviewed on May 22, 2026

Get rates
Congress Plaza Hotel
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! (4,211 reviews)
"I do a lot of traveling was very impressed by the staff money well spend"

Reviewed on May 23, 2026

Get rates
Hotel Riu Plaza Chicago
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! (1,455 reviews)
"the rooftop was great, room was clean, overall good for the price"

Reviewed on May 22, 2026

Get rates
The Chicago Hotel Collection - Magnificent Mile
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! (2,714 reviews)
"A decent buisness class hotel. No frills. Rooms are smaller, the queen beds are not true queens, and much smaller."

Reviewed on May 22, 2026

Get rates
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! (5,190 reviews)
"The staff was very helpful and friendly."

Reviewed on May 22, 2026

Get rates
River Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (3,016 reviews)
"The staff was lovely as always. The room was nice and clean."

Reviewed on May 22, 2026

Get rates
Freehand 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 ...
8.8/10 Excellent! (2,324 reviews)
"The location is very good, but the hotel needs to make some improvements. First, when you enter, there is a strong smell of humidity, which I imagine is coming from the carpet. The same smell was noticeable in the hallways and in the room. In the room, I found that the sink was clogged, and the shower ..."

Reviewed on May 21, 2026

Get rates
Holiday Inn Chicago Dwtn - The Mart by IHG
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (2,164 reviews)
"Amazing staff. Clean rooms!"

Reviewed on May 21, 2026

Get rates
Fairmont Chicago at Millennium Park
See all 5,027 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! (1,484 reviews)
"I highly recommend this hotel. The staff greets you upon walking in and in the morning as well. The rooms were clean and I felt safe in the location. I would definitely stay here again. Thank you!"

Reviewed on May 22, 2026

Get rates
William Tell Hotel MOD Collection by Sonesta
See all 5,027 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.