S$233 Cheap Flights from Chicago to Regina

View S$233 flight on Wed, 20 Aug, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Regina Intl. Airport (YQR)

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Cheap Flights from Chicago to Regina (ORD-YQR)

Prices were available within the past 7 days and start at S$233 for one-way flights and S$494 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, 20 Aug - Wed, 27 Aug
ORD
Chicago
YQR
Regina
S$494 Return, found 2 days ago
S$494
Return
found 2 days ago
Select United flight, departing Wed, 20 Aug from Chicago to Regina, returning Wed, 27 Aug, priced at S$494 found 2 days ago
WestJet
Wed, 20 Aug - Wed, 27 Aug
ORD
Chicago
YQR
Regina
S$500 Return, found 2 days ago
S$500
Return
found 2 days ago
Select WestJet flight, departing Wed, 20 Aug from Chicago to Regina, returning Wed, 27 Aug, priced at S$500 found 2 days ago
United
Wed, 20 Aug - Wed, 27 Aug
ORD
Chicago
YQR
Regina
S$502 Return, found 2 days ago
S$502
Return
found 2 days ago
Select United flight, departing Wed, 20 Aug from Chicago to Regina, returning Wed, 27 Aug, priced at S$502 found 2 days ago
WestJet
Wed, 20 Aug - Wed, 27 Aug
ORD
Chicago
YQR
Regina
S$517 Return, found 2 days ago
S$517
Return
found 2 days ago
Select WestJet flight, departing Wed, 20 Aug from Chicago to Regina, returning Wed, 27 Aug, priced at S$517 found 2 days ago
United
Wed, 20 Aug - Wed, 27 Aug
ORD
Chicago
YQR
Regina
S$528 Return, found 2 days ago
S$528
Return
found 2 days ago
Select United flight, departing Wed, 20 Aug from Chicago to Regina, returning Wed, 27 Aug, priced at S$528 found 2 days ago
United
Wed, 20 Aug - Wed, 27 Aug
ORD
Chicago
YQR
Regina
S$528 Return, found 2 days ago
S$528
Return
found 2 days ago
Select United flight, departing Wed, 20 Aug from Chicago to Regina, returning Wed, 27 Aug, priced at S$528 found 2 days ago
United
Wed, 20 Aug - Wed, 27 Aug
ORD
Chicago
YQR
Regina
S$533 Return, found 2 days ago
S$533
Return
found 2 days ago
Select United flight, departing Wed, 20 Aug from Chicago to Regina, returning Wed, 27 Aug, priced at S$533 found 2 days ago
WestJet
Wed, 20 Aug - Wed, 27 Aug
ORD
Chicago
YQR
Regina
S$536 Return, found 2 days ago
S$536
Return
found 2 days ago
Select WestJet flight, departing Wed, 20 Aug from Chicago to Regina, returning Wed, 27 Aug, priced at S$536 found 2 days ago
Air Canada
Wed, 20 Aug - Wed, 27 Aug
ORD
Chicago
YQR
Regina
S$545 Return, found 2 days ago
S$545
Return
found 2 days ago
Select Air Canada flight, departing Wed, 20 Aug from Chicago to Regina, returning Wed, 27 Aug, priced at S$545 found 2 days ago
WestJet
Wed, 20 Aug - Wed, 27 Aug
ORD
Chicago
YQR
Regina
S$548 Return, found 2 days ago
S$548
Return
found 2 days ago
Select WestJet flight, departing Wed, 20 Aug from Chicago to Regina, returning Wed, 27 Aug, priced at S$548 found 2 days ago

Find the cheapest month to fly from Chicago (ORD) to Regina (YQR)

May is typically the cheapest month to fly

From S$257 - S$888 per traveller.

Graph displaying average flight prices per month

Chicago to Regina route information
Origin airport
O'Hare Intl.
Destination airport
Regina Intl.
Return price
S$493
Distance
1580 km

Perfect flights from Chicago to Regina

Your Journey from Chicago to Regina

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Regina caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including United, WestJet, Air Canada, Delta, Alaska Airlines. Our selection of flights from O'Hare Intl. to Regina Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to Regina Flights

Experience the joy of finding cheap flights from O'Hare Intl. to Regina Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$233 and roundtrip prices from S$494*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Regina with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Regina

Picture yourself stepping off the plane in Regina and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to Regina Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to Regina.
 

Beyond the Flight – Exploring Regina

With Expedia, your adventure extends beyond the flight. Explore Regina at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to Regina with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to Regina with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from O'Hare Intl. Airport (ORD) to Regina Airport?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price quoted for a round-trip journey between ORD and Regina Intl. Airport (YQR) was S$494. Cheap fares don't hang around forever, so make sure you book yours ASAP. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Airport to Regina Airport?
The majority of flights can be conveniently cancelled online, but whether you incur a fee all comes down to your airline. If you do have to cancel your getaway, follow the instructions in the Customer Service Portal.
How do I find cheap flights from ORD to Regina Intl. Airport (YQR) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for O'Hare Airport to YQR flights, you'll see a "no change fees" filter for you to select.
How far is the flight from ORD to Regina Intl. Airport (YQR)?
You'll be up above the clouds for a while, as the flight distance from Chicago to Regina is 1,600 kilometres. Create a playlist of your favourite tunes before leaving home to stay entertained during your trip.
Which airlines fly direct from ORD to Regina Intl. Airport (YQR)?
There are no direct flights, so you'll have to make at least one stop between O'Hare Airport and Regina Intl. Airport (YQR). Make the most of the layover time to stretch your legs and grab a coffee.
Are O'Hare Intl. Airport (ORD) to Regina Airport flight tickets cheaper when they're purchased at the last minute?
It is possible to nab an amazing last-minute deal from O'Hare Airport to Regina Airport, but it's also possible to miss out altogether! As many airlines publish prices up to 12 months in advance, it's worth keeping an eye on fares early and being ready to pounce when you see a bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can rest easy knowing you're always seeing the latest offers.

Explore a world of travel with Expedia

Chicago Airports

Chicago

Midway Intl. to Regina
S$1,260.20
*Available to Expedia members.