Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

ORD - YQR

Find cheap flights from Chicago to Regina from $283

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 5/17. 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 6/1
Sat 6/8

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 43,740,974 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
12:04 pm - 6:58 pmORD-YQR
7h 54m1 stop
7:55 pm - 9:53 amYQR-ORD
12h 58m1 stop
Tue, Oct 1 - Tue, Oct 8
6:00 am - 2:25 pmORD-YQR
9h 25m1 stop
10:25 am - 6:26 pmYQR-ORD
7h 01m1 stop
$450Air Canada
Find Deal
Wed, Jun 12 - Sat, Jun 15
9:15 pm - 9:30 amORD-YQR
13h 15m1 stop
7:35 pm - 8:36 amYQR-ORD
12h 01m1 stop
$454Air Canada
Find Deal
Mon, Jun 24 - Wed, Jun 26
7:10 am - 6:40 pmORD-YQR
12h 30m1 stop
7:35 pm - 8:51 amYQR-ORD
12h 16m1 stop
$477Air Canada
Find Deal
Wed, Jun 12 - Sat, Jun 15
6:00 am - 6:40 pmORD-YQR
13h 40m1 stop
3:20 pm - 8:00 amYQR-ORD
15h 40m2 stops
$487Air Canada
Find Deal
Wed, Jun 12 - Sat, Jun 15
8:30 am - 11:10 pmORD-YQR
15h 40m2 stops
8:15 am - 9:03 pmYQR-ORD
11h 48m2 stops
$504Delta
Find Deal
Wed, Jun 12 - Sat, Jun 15
8:30 am - 11:10 pmORD-YQR
15h 40m2 stops
8:15 am - 9:03 pmYQR-ORD
11h 48m2 stops
$507Delta
Find Deal
Wed, Jun 12 - Sat, Jun 15
9:20 am - 2:28 pmORD-YQR
6h 08m1 stop
6:00 am - 6:34 pmYQR-ORD
11h 34m2 stops
$585Delta
Find Deal
Mon, Jun 24 - Wed, Jun 26
11:19 am - 10:54 pmORD-YQR
12h 35m2 stops
6:15 am - 9:04 pmYQR-ORD
13h 49m2 stops
$658WestJet
Find Deal
Tue, Oct 1 - Tue, Oct 8
6:00 am - 11:12 pmORD-YQR
18h 12m2 stops
11:40 am - 9:57 pmYQR-ORD
9h 17m2 stops
$740WestJet
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, Tuesday 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.

Which airlines provide the cheapest flights from Chicago to Regina?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Air Canada offered the best one-way deal for that route, at $557. KAYAK users also found Chicago to Regina round-trip flights on Air Canada from $450 and on Delta from $504.

Good to know

Low season

October

High season

August

Cheapest flight

$283
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 $283 for a one-way ticket and $409 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 6893 reviews
7.2Boarding
7.0Comfort
6.2Food
7.8Crew
6.8Entertainment
Airline reviews

All was good, except our baggage was lost for most of a day. We are thankful that it was found quickly and delivered to our hotel. Rouge was fine outside of that problem.

8.0 ExcellentJoe, May 2024MCO - YUL
Read more about Air Canada reviews

All was good, except our baggage was lost for most of a day. We are thankful that it was found quickly and delivered to our hotel. Rouge was fine outside of that problem.

You do not have a space for flight cancelled. BUT!!! Air Canada handled it great. Was booked on another airline for the next day. The original flight was booked solid. But he precheck by the maintenance found a mechanical problem and the plane was not safe to fly. It was an inconvenience to have to wait until next day but I would rather arrive safely.

Very good other than we have to wait for one crew and we’re delayed and the pilot and his co- pilot has to make a difference to be right on time arrival. Disappointed about no food service also.

I had written all my complaints on my trip from Grand Junction to Denver so I will repeat it here! I was absolutely appalled that I had to pay for a regular seat that I choose 24 hrs before boarding! Also I checked my large bag which I had to pay for as well, and by the time I boarded all the room in the bins were gone so also had to check that one. I noticed people pulling out oversized suitcases, bigger than the measurements stated for carry on, and also large pack packs stuffed full! So these people were taking up 2 or 3 spaces that the rest of us should have been able to use but couldn’t! NoTV on the flight! Thankfully I had downloaded the United Airlines app and was able to watch movies on my phone. Don’t remember the last time I flew in a plane with no movie screens!

Easy boarding, roomy seats, plenty of good food, very helpful snd friendly staff. Very smooth flight! Only thing that could have been better was to have cranberry juice. Women like this as it helps avoid UTI’s and not as sweet as other juices.

The crew was friendly, the seats are too small. Air travel is barely tolerable anymore.

Food was icecold or frozen including breakfast. Hopeless service. Rude crew.

The flight was very uncomfortable and there was no snacks served for the 13 hours international flight. In addition, the flight was delayed 3 hours

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

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.
5/17Fri
2 stops
22h 41mORD-YQR
$283
5/17Fri
3 stops
26h 59mORD-YQR
$302
5/17Fri
1 stop
19h 28mORD-YQR
$310
5/18Sat
2 stopsAir Canada
10h 55mORD-YQR
$557
5/17Fri
1 stopAir Canada
13h 33mORD-YQR
$586
5/18Sat
1 stopDelta
5h 36mORD-YQR
$715
5/17Fri
2 stopsAir Canada
10h 52mORD-YQR
$1,256
5/18Sat
3 stops
41h 51mORD-YQR
$6,292
5/17Fri
3 stops
42h 54mORD-YQR
$7,509

Search by stops

Search by airline

Search by price

Chicago - Regina Flights

Departure:

Chicago (ORD)United States

Destination:

Regina (YQR)Canada

Return flight deals:

Regina - Chicago

Cabin classes:

Browse destinations: