YQR - ORD

C$ 275 Find Cheap Flights from Regina to Chicago – 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 Regina to Chicago departing on 10/10. 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

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Everything you should know

Cheapest round-trip
C$ 510
Typical prices: C$ 383-C$ 618
WestJet
Wed 2/9Sat 5/9
YQR - ORD • 1 stop
Cheapest one-way flights
C$ 275
WestJet
Sat 10/10
YQR - ORD • 2 stops
Direct flights
Not available
There are currently no direct flights between Regina and Chicago. You’ll need at least 1 connection.
Insights
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Insights
Top layover airports
Calgary (YYC)
Cheapest • Avg C$ 431 (round-trip)
Minneapolis (MSP)
Shortest trip • 7h 07m (one-way)
Insights
Insights
Insights
Insights
When to travel
July
Cheapest • 100% price drop
May
Most popular
Good to know
Good to know
+1
+1
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Good to know
+1
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Regina to Chicago (YQR-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Regina to Chicago 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 Regina to Chicago

Wed, 2 Sep - Sat, 5 Sep
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 510WestJet
Wed, 2 Sep - Sat, 5 Sep
WestJet Logo
11:50 a.m. - 4:40 p.m.
YQR
-
ORD
27h 50m
2 stops
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 532WestJet
Wed, 2 Sep - Sat, 5 Sep
WestJet Logo
11:50 a.m. - 4:40 p.m.
YQR
-
ORD
27h 50m
2 stops
WestJet Logo
5:30 p.m. - 7:45 p.m.
ORD
-
YQR
27h 15m
2 stops
C$ 563WestJet
Fri, 16 Oct - Tue, 20 Oct
Delta Logo
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
Delta Logo
12:33 p.m. - 5:20 p.m.
ORD
-
YQR
5h 47m
1 stop
C$ 571Delta
Mon, 7 Sep - Fri, 11 Sep
United Airlines Logo
2:15 p.m. - 10:05 p.m.
YQR
-
ORD
6h 50m
1 stop
United Airlines Logo
5:55 a.m. - 9:30 p.m.
ORD
-
YQR
16h 35m
1 stop
C$ 595United Airlines
Mon, 7 Sep - Fri, 11 Sep
Air Canada Logo
2:15 p.m. - 10:05 p.m.
YQR
-
ORD
6h 50m
1 stop
Air Canada Logo
12:59 p.m. - 7:05 p.m.
ORD
-
YQR
7h 06m
1 stop
C$ 608Air Canada
Mon, 7 Sep - Fri, 11 Sep
WestJet Logo
8:20 p.m. - 4:40 p.m.
YQR
-
ORD
19h 20m
2 stops
WestJet Logo
5:30 p.m. - 11:20 p.m.
ORD
-
YQR
6h 50m
1 stop
C$ 610WestJet
Mon, 7 Sep - Fri, 11 Sep
WestJet Logo
11:40 a.m. - 4:40 p.m.
YQR
-
ORD
28h 00m
1 stop
WestJet Logo
5:30 p.m. - 11:20 p.m.
ORD
-
YQR
6h 50m
1 stop
C$ 615WestJet
Fri, 16 Oct - Tue, 20 Oct
Delta Logo
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
Delta Logo
12:33 p.m. - 5:20 p.m.
ORD
-
YQR
5h 47m
1 stop
C$ 638Delta
Tue, 10 Nov - Fri, 25 Dec
Multiple Airlines Logo
10:45 a.m. - 10:44 p.m.
YQR
-
ORD
11h 59m
1 stop
Multiple Airlines Logo
4:30 p.m. - 11:27 p.m.
ORD
-
YQR
6h 57m
1 stop
C$ 700Multiple Airlines
Booking Insights

KAYAK's insights & trends for Regina to Chicago flights

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Regina to Chicago O'Hare Intl Airport, 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 Regina to Chicago O'Hare Intl Airport is July, where tickets cost C$ 0 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is C$ 1,199 and C$ 1,109 respectively.

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Good to know

Low seasonFebruary
Cheapest flightC$ 275
Best time to beat the crowds (58% less expensive on average)
Most popular time to fly and prices are also 28% lower on average.
Flight from Regina to Chicago

When to book flights from Regina to Chicago

Are your dates flexible? Find out the best times to travel from Regina to Chicago 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 Regina to Chicago flights

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

    In the last 5 days, the lowest price for a flight from Regina to Chicago O'Hare Intl Airport was C$ 275 for a one-way ticket and C$ 510 for a round-trip.

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

    Regina and Chicago are both served by 1 main airport. You will leave Regina from Regina and will be arriving at Chicago O'Hare Intl.

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

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

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

    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 Regina to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Regina 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 Regina to Chicago?

    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 Chicago with an airline and back to Regina with another airline.

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

    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 Chicago from Regina 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 Regina to Chicago

Information on your arrival and departure airports

Regina (YQR)
O'Hare Intl (ORD)