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ORD - YQR

Find cheap flights from Chicago to Regina from $415

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Regina departing on 5/14. 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
Sat 5/25
Sat 6/1

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 45,119,101 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
9:25 pm - 2:28 pmORD-YQR
18h 03m2 stops
8:35 pm - 5:05 pmYQR-ORD
19h 30m1 stop
Tue, May 14 - Wed, May 29
12:32 pm - 9:58 amORD-YQR
22h 26m2 stops
8:15 am - 5:35 pmYQR-ORD
8h 20m1 stop
Sat, Jun 29 - Thu, Jul 4
9:25 pm - 2:28 pmORD-YQR
18h 03m2 stops
3:05 pm - 5:05 pmYQR-ORD
25h 00m2 stops
Tue, May 14 - Wed, May 29
6:00 am - 2:25 pmORD-YQR
9h 25m1 stop
7:35 pm - 7:57 amYQR-ORD
11h 22m1 stop
$435Air Canada
Find Deal
Wed, May 15 - Thu, May 30
6:00 am - 2:25 pmORD-YQR
9h 25m1 stop
7:35 pm - 10:01 amYQR-ORD
13h 26m2 stops
$440Air Canada
Find Deal
Wed, May 15 - Thu, May 30
6:20 am - 2:28 pmORD-YQR
9h 08m1 stop
8:15 am - 4:55 pmYQR-ORD
7h 40m1 stop
$446Delta
Find Deal
Wed, May 1 - Sat, May 4
6:20 am - 2:28 pmORD-YQR
9h 08m1 stop
8:15 am - 11:52 pmYQR-ORD
14h 37m2 stops
$455Delta
Find Deal
Wed, May 1 - Sat, May 4
7:09 am - 11:10 pmORD-YQR
17h 01m2 stops
6:00 am - 4:49 pmYQR-ORD
9h 49m2 stops
$590WestJet
Find Deal
Wed, May 15 - Thu, May 30
12:47 pm - 6:40 pmORD-YQR
30h 53m2 stops
7:35 pm - 6:28 pmYQR-ORD
21h 53m2 stops
$732United Airlines
Find Deal
Sat, Jun 29 - Sun, Jul 7
6:00 am - 11:12 pmORD-YQR
18h 12m2 stops
10:05 am - 9:57 pmYQR-ORD
10h 52m2 stops
$754WestJet
Find Deal
Mon, Jun 24 - Wed, Jun 26

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

$415
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 $415 for a round-trip ticket.

  • 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 Star Alliance 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 6857 reviews
7.8crew
6.2food
7.0comfort
6.8entertainment
7.2boarding
Airline reviews

Due to a strike taking place with the airline, it negatively impacted my flight in multiple ways. My flight was delayed over 2 hours and the food served was mediocre at best.

4.0 OkayJarrett, Apr 2024LAX - YYZ
Read more about Air Canada reviews

Due to a strike taking place with the airline, it negatively impacted my flight in multiple ways. My flight was delayed over 2 hours and the food served was mediocre at best.

Cabin crew were great. Seats are criminal for tall people

Flight was delayed 1.5 hrs due to problem with a previous flight to mine; I was informed appropriately via Text & Email, however, website did not keep up with messages sent by nearly an hour. When checking-in warm & friendly reception at check-in desk until female Air Canada Rep noticed my flight number and instantly pivoted to a condescending & sarcastic comments about getting my bag checked in since I’m running so late; then tone instantly changed again few minutes later when she muttered, “Oh, they’ve delayed it” another sign systems & worse front line staff, not fully informed or simply not reading their flight status updates. Flight crew were very friendly & did a great job trying to make up lost time due to the delay.

It was great, love the experience and will definitely recommend 👌. Communication was great

My flight was great! Gate attendants and crew were great… pleasant and in good spirits. Flight delayed several hours and we were well informed of the status while on plane. Thank you!

The fact that I got to Toronto alive and well and safe is a huge plus. I thank the captain and crew for a safe flight The comfort of the aircraft leaves much to be desired. Human beings should not have to be that cramped and squashed on a flight that we pay a lot for and even have to pay for lousy food choices The cabin crew were pleasant and helpful Kudos to them as the flight was packed to capacity and there was a lot of work for them in a short space of time All in all a good experience, but too cramped

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!

Chicago - Regina Flights

Departure:

Chicago (ORD)United States

Destination:

Regina (YQR)Canada

Return flight deals:

Regina - Chicago

Cabin classes:

Browse destinations: