$348 Cheap Flights from Regina (YQR) to Chicago (MDW)

View $348 flight on Thu, Sep 18, 2025Opens in a new window

Popular airlines from Regina Intl. Airport (YQR) to Chicago Midway Airport (MDW)

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Cheap Flights from Regina to Chicago (YQR-MDW)

Prices were available within the past 7 days and start at $348 for one-way flights and $775 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Sat, Aug 30 - Sat, Sep 6
YQR
Regina
MDW
Chicago
$775 Roundtrip, found 3 days ago
$775
Roundtrip
found 3 days ago
Select WestJet flight, departing Sat, Aug 30 from Regina to Chicago, returning Sat, Sep 6, priced at $775 found 3 days ago
WestJet
Fri, Jul 25 - Mon, Jul 28
YQR
Regina
MDW
Chicago
$786 Roundtrip, found 2 days ago
$786
Roundtrip
found 2 days ago
Select WestJet flight, departing Fri, Jul 25 from Regina to Chicago, returning Mon, Jul 28, priced at $786 found 2 days ago
WestJet
Thu, Sep 18 - Mon, Sep 22
YQR
Regina
MDW
Chicago
$832 Roundtrip, found 1 day ago
$832
Roundtrip
found 1 day ago
Select WestJet flight, departing Thu, Sep 18 from Regina to Chicago, returning Mon, Sep 22, priced at $832 found 1 day ago
WestJet
Mon, Jul 28 - Tue, Aug 5
YQR
Regina
MDW
Chicago
$891 Roundtrip, found 6 days ago
$891
Roundtrip
found 6 days ago
Select WestJet flight, departing Mon, Jul 28 from Regina to Chicago, returning Tue, Aug 5, priced at $891 found 6 days ago
WestJet
Mon, Jul 28 - Sun, Aug 3
YQR
Regina
MDW
Chicago
$925 Roundtrip, found 6 days ago
$925
Roundtrip
found 6 days ago
Select WestJet flight, departing Mon, Jul 28 from Regina to Chicago, returning Sun, Aug 3, priced at $925 found 6 days ago
WestJet
Mon, Jul 28 - Sun, Aug 3
YQR
Regina
MDW
Chicago
$935 Roundtrip, found 6 days ago
$935
Roundtrip
found 6 days ago
Select WestJet flight, departing Mon, Jul 28 from Regina to Chicago, returning Sun, Aug 3, priced at $935 found 6 days ago
WestJet
Thu, Sep 18 - Mon, Sep 22
YQR
Regina
MDW
Chicago
$1,088 Roundtrip, found 1 day ago
$1,088
Roundtrip
found 1 day ago
Select WestJet flight, departing Thu, Sep 18 from Regina to Chicago, returning Mon, Sep 22, priced at $1,088 found 1 day ago
WestJet
Thu, Sep 18 - Mon, Sep 22
YQR
Regina
MDW
Chicago
$1,440 Roundtrip, found 1 day ago
$1,440
Roundtrip
found 1 day ago
Select WestJet flight, departing Thu, Sep 18 from Regina to Chicago, returning Mon, Sep 22, priced at $1,440 found 1 day ago
WestJet
Sat, Aug 30 - Sat, Sep 6
YQR
Regina
MDW
Chicago
$1,444 Roundtrip, found 3 days ago
$1,444
Roundtrip
found 3 days ago
Select WestJet flight, departing Sat, Aug 30 from Regina to Chicago, returning Sat, Sep 6, priced at $1,444 found 3 days ago
WestJet
Fri, Jul 25 - Mon, Jul 28
YQR
Regina
MDW
Chicago
$1,454 Roundtrip, found 2 days ago
$1,454
Roundtrip
found 2 days ago
Select WestJet flight, departing Fri, Jul 25 from Regina to Chicago, returning Mon, Jul 28, priced at $1,454 found 2 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $560
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $560
Flights from Regina (YQR) to Chicago (MDW)
Origin airport
Regina Intl.
Destination airport
Midway Intl.
Airlines serving
WestJet
Roundtrip price
$775
Distance
1002 mi

Frequently asked questions

How much does a flight from Regina Intl. Airport (YQR) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from YQR to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from YQR to MDW?
The cheapest flights from YQR to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from YQR to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from YQR to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Regina Intl. Airport (YQR) to Midway Intl. Airport (MDW)?
You'll need to book a flight with a layover when traveling from Regina Intl. Airport (YQR) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, just filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from YQR to MDW?
Friday is generally the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change depending on a number of factors, including the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Regina Intl. Airport (YQR) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Regina Intl. Airport (YQR) to Midway Intl. Airport (MDW) route, aim to fly before 3 PM. Later departures have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Regina Intl. Airport (YQR) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from YQR to MDW are generally more expensive. For the lowest rates, start looking for flights early. That said, if you're flexible with your travel plans, you may score a cheap ticket right before your journey.
Is it cheaper to book a YQR to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a YQR to MDW flight and hotel package with Expedia could lead to significant savings. Better still, having it all in one place takes the hassle out of planning your trip. Just pick your flights and select from our extensive range of stays, then customize your trip with extras like activities and car rentals.
Can I cancel or change the date of my flight from Regina Intl. Airport (YQR) to Midway Intl. Airport (MDW)?
Generally, it's possible to cancel or reschedule your YQR to MDW flight. However, if it's been more than 24 hours since booking, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find further details on our Customer Service portal.

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