ORD - YQR

C$ 228 Find Cheap Flights from Chicago to Regina – Compare and Save

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 9/10. 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
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
C$ 480
WestJet
Thu 17/9Thu 24/9
ORD - YQR • 1 stop
Cheapest one-way flights
C$ 228
WestJet
Fri 9/10
ORD - YQR • 1 stop
Direct flights
Not available
There are currently no direct flights between Chicago and Regina. You’ll need at least 1 connection.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 100% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Regina!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Regina

Thu, 17 Sep - Thu, 24 Sep
WestJet Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 40m1 stop Calgary
C$ 480WestJet
Wed, 16 Sep - Wed, 23 Sep
Air Canada Logo
8:45 a.m. - 7:05 p.m.ORD  Chicago O'Hare Intl-YQR Regina
11h 20m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
5:45 a.m. - 1:23 p.m.YQR  Regina-ORD Chicago O'Hare Intl
6h 38m1 stop Toronto Pearson Intl
C$ 515Air Canada
Wed, 16 Sep - Wed, 23 Sep
Multiple Airlines Logo
8:40 p.m. - 3:40 p.m.ORD  Chicago O'Hare Intl-YQR Regina
20h 00m2 stops Toronto Pearson Intl Calgary
Multiple Airlines Logo
12:40 p.m. - 7:48 p.m.YQR  Regina-ORD Chicago O'Hare Intl
6h 08m1 stop Toronto Pearson Intl
C$ 520Multiple Airlines
Wed, 16 Sep - Wed, 23 Sep
Multiple Airlines Logo
8:40 p.m. - 12:45 p.m.ORD  Chicago O'Hare Intl-YQR Regina
17h 05m2 stops Toronto Pearson Intl Calgary
Multiple Airlines Logo
8:35 a.m. - 7:48 p.m.YQR  Regina-ORD Chicago O'Hare Intl
10h 13m2 stops Calgary Toronto Pearson Intl
C$ 524Multiple Airlines
Wed, 16 Sep - Wed, 23 Sep
Multiple Airlines Logo
9:55 a.m. - 12:35 a.m.ORD  Chicago O'Hare Intl-YQR Regina
15h 40m1 stop Toronto Pearson Intl
Multiple Airlines Logo
5:45 a.m. - 2:50 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 05m1 stop Toronto Pearson Intl
C$ 538Multiple Airlines
Thu, 17 Sep - Thu, 24 Sep
Air Canada Logo
8:45 a.m. - 7:05 p.m.ORD  Chicago O'Hare Intl-YQR Regina
11h 20m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
5:45 a.m. - 2:55 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
C$ 542Air Canada
Wed, 16 Sep - Wed, 23 Sep
Multiple Airlines Logo
8:40 p.m. - 3:40 p.m.ORD  Chicago O'Hare Intl-YQR Regina
20h 00m2 stops Toronto Pearson Intl Calgary
Multiple Airlines Logo
8:35 a.m. - 7:48 p.m.YQR  Regina-ORD Chicago O'Hare Intl
10h 13m2 stops Calgary Toronto Pearson Intl
C$ 546Multiple Airlines
Wed, 16 Sep - Wed, 23 Sep
Air Canada Logo
8:45 a.m. - 7:05 p.m.ORD  Chicago O'Hare Intl-YQR Regina
11h 20m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
12:40 p.m. - 7:48 p.m.YQR  Regina-ORD Chicago O'Hare Intl
6h 08m1 stop Toronto Pearson Intl
C$ 556Air Canada
Thu, 17 Sep - Thu, 24 Sep
Air Canada Logo
8:45 a.m. - 7:05 p.m.ORD  Chicago O'Hare Intl-YQR Regina
11h 20m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
11:20 a.m. - 9:00 a.m.YQR  Regina-ORD Chicago O'Hare Intl
20h 40m2 stops Saskatoon Toronto Pearson Intl
C$ 558Air Canada
Wed, 16 Sep - Wed, 23 Sep
Air Canada Logo
9:55 a.m. - 7:05 p.m.ORD  Chicago O'Hare Intl-YQR Regina
10h 10m1 stop Toronto Pearson Intl
Air Canada Logo
5:45 a.m. - 1:23 p.m.YQR  Regina-ORD Chicago O'Hare Intl
6h 38m1 stop Toronto Pearson Intl
C$ 593Air Canada
Booking Insights

KAYAK's insights & trends for Chicago to Regina flights

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 is the cheapest month to fly from Chicago O'Hare Intl Airport to Regina?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Regina, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Regina is January, where tickets cost C$ 0 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is C$ 1,608 and C$ 1,212 respectively.

Find deals

Good to know

Low season

August

Cheapest flight

C$ 228
Best time to beat the crowds (49% less expensive on average)
Most popular time to fly and prices are also 4% 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 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Regina was C$ 228 for a one-way ticket and C$ 480 for a round-trip.

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

    Chicago airport is called Chicago O'Hare Intl and the only airport in Regina is Regina.

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

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

  • 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.

Everything you need to know for your flight from Chicago to Regina

Information on your arrival and departure airports

Chicago (ORD)
Regina (YQR)