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ORD - YQR

Find cheap flights from Chicago to Regina from $196

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Regina departing on 5/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sun 5/19
Sun 5/26

Search hundreds of travel sites at once for deals on flights to Regina

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Regina, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Regina, as well as popular online travel agencies
In the last 7 days travelers have searched 44,212,662 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Chicago to Regina (ORD-YQR)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Regina that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:23 pm - 12:56 amORD-YQR
29h 33m2 stops
8:15 am - 7:10 pmYQR-ORD
9h 55m1 stop
Tue, Jun 11 - Thu, Jun 20
8:00 pm - 2:28 pmORD-YQR
19h 28m1 stop
8:15 am - 7:03 pmYQR-ORD
9h 48m1 stop
Thu, May 16 - Thu, May 23
5:55 pm - 12:56 amORD-YQR
8h 01m1 stop
11:40 am - 5:05 pmYQR-ORD
28h 25m1 stop
$397WestJet
Find Deal
Sat, May 18 - Sat, May 25
5:55 pm - 10:00 amORD-YQR
17h 05m2 stops
11:40 am - 5:05 pmYQR-ORD
28h 25m1 stop
$423WestJet
Find Deal
Sat, May 18 - Sat, May 25
10:00 pm - 2:28 pmORD-YQR
17h 28m2 stops
10:45 am - 6:30 amYQR-ORD
18h 45m3 stops
Tue, May 7 - Tue, May 21
10:00 pm - 2:28 pmORD-YQR
17h 28m2 stops
8:35 pm - 9:55 pmYQR-ORD
24h 20m2 stops
Tue, May 7 - Tue, May 21
9:15 pm - 9:30 amORD-YQR
13h 15m1 stop
7:35 pm - 7:57 amYQR-ORD
11h 22m1 stop
$514Air Canada
Find Deal
Mon, Jun 24 - Wed, Jun 26
9:15 pm - 9:30 amORD-YQR
13h 15m1 stop
3:20 pm - 7:52 amYQR-ORD
15h 32m2 stops
$548Air Canada
Find Deal
Mon, Jun 24 - Wed, Jun 26
12:15 pm - 2:28 pmORD-YQR
27h 13m1 stop
8:15 am - 8:35 amYQR-ORD
23h 20m1 stop
$736Delta
Find Deal
Sat, Apr 27 - Tue, Apr 30
3:50 pm - 2:28 pmORD-YQR
23h 38m1 stop
8:15 am - 4:50 pmYQR-ORD
7h 35m1 stop
$759Delta
Find Deal
Sat, Apr 27 - Tue, Apr 30

Flights from Chicago to Regina - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to Regina to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Regina?

The average price of all flights from Chicago O'Hare Intl Airport to Regina clicked on KAYAK for each day over the last 12 months.
For Chicago to Regina, Monday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Regina back to Chicago, the best deals are generally found on Monday, with Thursday being the most expensive.

Good to know

Low season

October

High season

August

Cheapest flight

$196
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Chicago to Regina

When to book flights from Chicago to Regina

Are your dates flexible? Find out the best times to travel from Chicago to Regina based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Regina flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Regina?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Regina was $196 for a one-way ticket and $382 for a round-trip.

  • Do I need a passport to fly between Chicago and Regina?

    A passport is required to fly from Chicago to Regina.

  • Which airports will I be using when flying from Chicago to Regina?

    On your way to Regina, you’ll fly out from Chicago O'Hare Intl. You’ll be landing at Regina.

  • Which aircraft models fly most regularly from Chicago to Regina?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Regina?

    Star Alliance, and SkyTeam are the airline alliances operating flights between Chicago and Regina, with SkyTeam being the most commonly used for this route.

  • How does KAYAK find such low prices on flights from Chicago to Regina?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Regina.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Regina?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Regina from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Regina?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Regina with an airline and back to Chicago with another airline. Booking your flights between Chicago and YQR can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Regina?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Regina from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Chicago to Regina

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Regina. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Regina? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.0
Air CanadaOverall score based on 6844 reviews
7.2boarding
7.8crew
6.8entertainment
7.0comfort
6.2food
Airline reviews

It was great to check carryon luggage at no charge when there was no room for ours. A hidden benefit of having low-tier tickets. Also great to stay off plane as long as possible. Airline gave us seats we wanted on this last leg, again at no charge.

8.0 ExcellentAnonymous, Apr 2024DEN - YVR
Read more about Air Canada reviews

It was great to check carryon luggage at no charge when there was no room for ours. A hidden benefit of having low-tier tickets. Also great to stay off plane as long as possible. Airline gave us seats we wanted on this last leg, again at no charge.

The late departure Of two hours waitresses, immature, and gossiping

We had a good flight, service was good and lots of leg room. Service was good and the staff were friendly.

Overall I will say it was a very good experience. It was as comfortable as can be expected for such a long flight - 12 hours from Toronto to Tokyo. Everyone was very pleasant and polite. Even the passengers were cooperative and trying to be nice to each other. Of course the space is limited on such a long flight. The bathrooms were actually very clean. The food was very good. I liked how there was a variety of food options. The in flight entertainment system was also very impressive! There were some children on the flight but they were well behaved and hardly ever crying. Great Job Canada Air! I will definitely fly with Air Canada again!

It was upsetting that the flights were canceled but that was due to weather. I did not receive any vouchers for food or a hotel stay when I was forced to spend the night in Montreal. I was also upset when my seat was changed many times.. The plane seemed old with a non-functioning screen and loose side pockets.. All in all in need of updating. On the positive side, the staff in areas was friendly and helpful.

Lost my bag. My first ever flight with them that they forced me to gate check my bag on, due to them having a 30 year old plane with small carry on bins, and they lost my bag. Never again.

The flight got canceled multiple times and we had to drive their to reach midnight for our next morning interview. Poor and unriable experience. Now have to ask for a refund since we didn't need their rescheduled flight three days later.

Short flight, crew members were very nice, so much so I'll take the return flight next weekend

The trip was fine and uneventful. The seat in business class was very uncomfortable which was disappointing given the extra cost. It was spacious but it felt like I was sitting on metal bars. The food in business class wasn't very good. The flight was ahead of time, the staff was professional and courteous and our luggage arrived safely.

Again we were late leaving Austin , there was no tv screen for the 3.5 hr flight, the pizza I bought was kinda bland

Book cheap flights from Chicago to Regina

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Regina found on KAYAK in the last 72 hours.
5/16Thu
1 stop
19h 28mORD-YQR
$196
5/16Thu
2 stops
18h 16mORD-YQR
$320
5/16Thu
3 stops
29h 56mORD-YQR
$330

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Chicago - Regina Flights

Departure:

Chicago (ORD)United States

Destination:

Regina (YQR)Canada

Return flight deals:

Regina - Chicago

Cabin classes:

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