Find the cheapest flights on Expedia from Chicago (MDW) to Regina (YQR). Flight ticket prices change frequently based on availability and demand. We send price‑drop alerts to make air travel simple and flexible. The lowest one-way fare found on Expedia for this route in the past 7 days starts at CA $533 for travel on January 5, 2027.
Cheap Flights from Chicago to Regina (MDW-YQR)
Prices were available within the past 7 days and start at CA $533 for one-way flights and CA $1,147 for roundtrip, for the period specified. Prices and availability are subject to change.
The easy way to book your flights from Chicago to Regina
With Expedia, it’s simple to find and book flights to Regina from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 2 airlines that cover this route. There are nonstop flights to Regina Intl., too.
Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to Regina today, tomorrow, or this week.
Save dollars with cheap flights from Midway Intl., MDW to Regina Intl., YQR
Sort your search results by price to find great deals on your flight from Chicago to Regina—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Regina from Chicago currently is just CA $1,147 rising to CA $1,610.
Here are more money-saving tips:
Fly in January when flight prices are normally at their lowest
Book about a month to 6 weeks before you travel for the best prices to Regina
Avoid peak season and weekends when flights can cost more
Early morning and late-night flights are sometimes cheaper, so try varying your travel times
One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!
Reasons to choose Expedia for your flight to Regina from Chicago
Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Regina with Expedia today.
Frequently Asked Questions
How much is a flight from Midway Airport to Regina Airport?
If you're planning on travelling from Chicago Airport to Regina Airport, round-trip journeys start from CA $1,147. This figure is based on fares available within the last 7 days on Expedia for flights departing within the next year, so don't wait around. Book now and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MDW to Regina Intl. Airport (YQR)?
We understand that life can throw the odd curveball, so we've made it as hassle-free as possible for you to cancel your flight online. Just head to the Customer Service Portal and follow the instructions.
How do I find cheap flights from Midway Airport to Regina Intl. Airport (YQR) that have flexible change policies?
Flights from MDW to Regina Intl. Airport (YQR) with flexible change policies are available from several airlines. Simply use our "No change fees" filter while searching. You'll only need to cover the fare difference, with no extra fees to worry about.
How far is the flight from Midway Airport to Regina Airport?
Around 1,600 kilometres separates Chicago and Regina, so pack some in-flight entertainment to help you while away a few hours. That gripping novel you haven't had time to finish will be ideal.
Which airlines fly direct from MDW to YQR?
If you want to fly straight from Midway Airport to YQR, you'll have to book a flight with at least one stop. Unfortunately, there are no airlines that fly directly between these airports.
Are Midway Intl. Airport (MDW) to Regina Intl. Airport (YQR) flight tickets cheaper when they're purchased at the last minute?
It is possible to nab an awesome last-minute deal from Midway Intl. Airport (MDW) to Regina Intl. Airport (YQR), but it can also be hit-or-miss. As many airlines release prices up to 12 months in advance, it's worthwhile keeping an eye on fares early and being ready to pounce when you spot 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.