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Countryside

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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 , 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  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 , 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  right now, why wait?

Countryside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$172

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 free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (9,338 reviews)
"This was our second stay at this hotel and we will probably stay here for all our future trips to Chicago. It's very conveniently located, making it very easy to get to and from Midway Airport and all the things we want to see and do in town. There are tons of great restaurants within walking distance ..."

Reviewed on Sep 28, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,402 reviews)
"Everything was great"

Reviewed on Sep 27, 2025

Freehand Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (5,014 reviews)
"I love the two room suites at Embassy suites. someone can sleep in one room while the other person has lights on in the living area. Also the breakfast is great!"

Reviewed on Sep 28, 2025

Embassy Suites by Hilton Chicago Downtown River North
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 ...
8.8/10 Excellent! (3,003 reviews)
"Great"

Reviewed on Sep 27, 2025

Hilton Chicago/Magnificent Mile Suites
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (3,859 reviews)
"—"

Reviewed on Sep 24, 2025

citizenM Chicago Downtown
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (4,009 reviews)
"Great location in Chicago. Close to good restaurants. Red Line right outside of hotel."

Reviewed on Sep 28, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (2,446 reviews)
"I love staying at the Intercontinental. It is in a great location, and the hotel itself is lovely, historic, and home to the most spectacular swimming pools I've ever seen. I love to start my days there with a dip in the Olympic-sized pool where Johnny Weissmuller trained."

Reviewed on Sep 27, 2025

InterContinental Chicago Magnificent Mile by IHG
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 breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
8.8/10 Excellent! (2,079 reviews)
Best hotel for a romantic getaway
"We truly can’t wait to come back to this hotel. Allegro is gorgeous, elegant, and comfortable. It has a fun history and was a featured stop on our Art Deco architectural tour!"

Reviewed on Sep 28, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
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

Holiday Inn Chicago SW-Countryside ConfCtr by IHG

Holiday Inn Chicago SW-Countryside ConfCtr by IHG

3.5 out of 5
6201 Joliet Rd, Countryside, IL
Stay at this 3.5-star business-friendly hotel in Countryside. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the clean rooms ...
7.8/10 Good! (1,162 reviews)
"Always clean amd friendly staff when I stay here. Parking is very easy and well lit for safety. Very close to a shopping mall to grab anything you may need as well! Highly recommend."

Reviewed on Sep 23, 2025

Holiday Inn Chicago SW-Countryside ConfCtr by IHG
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.