ORD - YQR

C$ 518 Find Cheap Flights from Chicago to Regina – Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
C$ 518
Typical prices: C$ 726-C$ 1,061
WestJet
Mon 15/10Tue 23/10
ORD - YQR • 1 stop
Direct flights
Not available
There are currently no direct flights between Chicago O'Hare Intl Airport and Regina. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
October
Cheapest • 45% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Calgary (YYC)
Cheapest • Avg C$ 778 (round-trip)
Minneapolis St Paul (MSP)
Shortest trip • 6h 10m (one-way)
Insights
Insights
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We hope you enjoy your trip to Regina!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Regina (ORD-YQR)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Regina

Thu, 15 Oct - Fri, 23 Oct
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$ 518WestJet
Thu, 15 Oct - Thu, 22 Oct
WestJet Logo
5:30 p.m. - 11:20 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
WestJet Logo
8:35 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
7h 05m1 stop Calgary
C$ 531WestJet
Mon, 23 Nov - Thu, 3 Dec
Air Canada Logo
8:40 p.m. - 10:43 a.m.ORD  Chicago O'Hare Intl-YQR Regina
14h 03m1 stop Toronto Pearson Intl
Air Canada Logo
5:00 a.m. - 1:13 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 13m1 stop Toronto Pearson Intl
C$ 551Air Canada
Mon, 30 Nov - Wed, 9 Dec
Air Canada Logo
3:45 p.m. - 10:43 a.m.ORD  Chicago O'Hare Intl-YQR Regina
18h 58m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
5:00 a.m. - 7:52 p.m.YQR  Regina-ORD Chicago O'Hare Intl
14h 52m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
C$ 569Air Canada
Sat, 17 Oct - Thu, 22 Oct
Multiple Airlines Logo
1:30 p.m. - 9:30 p.m.ORD  Chicago O'Hare Intl-YQR Regina
9h 00m1 stop Denver Intl
Multiple Airlines Logo
5:40 a.m. - 2:55 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 15m1 stop Toronto Pearson Intl
C$ 570Multiple Airlines
Mon, 30 Nov - Wed, 9 Dec
Air Canada Logo
8:40 p.m. - 10:43 a.m.ORD  Chicago O'Hare Intl-YQR Regina
14h 03m1 stop Toronto Pearson Intl
Air Canada Logo
5:00 a.m. - 1:13 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 13m1 stop Toronto Pearson Intl
C$ 573Air Canada
Wed, 18 Nov - Tue, 24 Nov
Air Canada Logo
4:30 p.m. - 11:27 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 57m1 stop Toronto Pearson Intl
Air Canada Logo
5:00 a.m. - 1:13 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 13m1 stop Toronto Pearson Intl
C$ 575Air Canada
Mon, 30 Nov - Wed, 9 Dec
Air Canada Logo
3:45 p.m. - 10:43 a.m.ORD  Chicago O'Hare Intl-YQR Regina
18h 58m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
5:00 a.m. - 1:13 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 13m1 stop Toronto Pearson Intl
C$ 576Air Canada
Thu, 15 Oct - Fri, 23 Oct
WestJet Logo
5:30 p.m. - 11:15 a.m.ORD  Chicago O'Hare Intl-YQR Regina
18h 45m2 stops Calgary Edmonton
WestJet Logo
8:35 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
7h 05m1 stop Calgary
C$ 583WestJet
Wed, 18 Nov - Tue, 24 Nov
Air Canada Logo
4:30 p.m. - 11:27 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 57m1 stop Toronto Pearson Intl
Air Canada Logo
5:00 a.m. - 2:52 p.m.YQR  Regina-ORD Chicago O'Hare Intl
9h 52m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
C$ 587Air Canada
Booking Insights

Price, demand, and travel trends for Chicago O'Hare Intl Airport to Regina flights

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights from Chicago O'Hare Intl Airport to Regina with more confidence.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Regina?

Round-trip flights from Chicago O'Hare Intl Airport to Regina start at C$ 518. Prices are below average for this route right now, with typical round-trip fares ranging from C$ 726 to C$ 1,061. The lowest price found in the past 5 days was C$ 518 on WestJet.

What's the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Regina?

Tuesday is the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Regina and is 36% cheaper than the average day. Saturday is the most expensive day with flight prices 88% higher than average. Based on deals found by KAYAK users in the last 12 months.

Find deals

Key details for Chicago O'Hare Intl Airport to Regina flights

Low season

January

Cheapest flight

C$ 518
Flights from Chicago O'Hare Intl Airport 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

Your Chicago O'Hare Intl Airport to Regina flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines, and booking questions.

  • Which cabin classes can I book on flights from Chicago O'Hare Intl Airport to Regina?

    Only Economy Class is available on flights from Chicago O'Hare Intl Airport to Regina.

  • How long does a flight from Chicago O'Hare Intl Airport to Regina take?

    A direct flight from Chicago O'Hare Intl Airport to Regina takes 0h 00m, covering 2,557 km.

  • Do I need a passport to fly from Chicago O'Hare Intl Airport to Regina?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Chicago O'Hare Intl Airport to Regina flight?

    Round-trip flights from Chicago O'Hare Intl Airport to Regina range from C$ 726 to C$ 1,061, with an average of C$ 860 over the past 12 months. Anything below C$ 726 counts as a good deal.

  • Have flight prices from Chicago O'Hare Intl Airport to Regina changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about C$ 518 to C$ 1,481. That means the highest observed fare was about 3x higher than the lowest one.

  • What car rental options are available at Regina Airport (YQR)?

    Regina Airport (YQR) hosts 5 major car rental companies, with daily rates starting from around C$ 30 for economy cars. Top options include:
    • Hertz
    • Enterprise Rent-A-Car
    • Budget
    • National
    • Avis

  • Which airports can I use when flying from Chicago O'Hare Intl Airport to Regina?

    Flights from Chicago O'Hare Intl Airport to Regina usually depart from Chicago O'Hare Intl (ORD) and arrive at Regina (YQR).

  • Which airports do connecting flights from Chicago O'Hare Intl Airport to Regina pass through?

    One-stop flights from Chicago O'Hare Intl Airport to Regina most commonly connect through:

    • Denver Intl (DEN) – 41% of one-stop connections
    • Minneapolis St Paul (MSP) – 24% of one-stop connections
    • Toronto Pearson Intl (YYZ) – 18% of one-stop connections
    • Calgary (YYC) – 16% of one-stop connections

    Denver Intl (DEN) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Chicago O'Hare Intl Airport to Regina?

    Yes. Being flexible with your travel dates can save you up to 66% on the Chicago O'Hare Intl Airport to Regina route. Tuesday is the cheapest departure day at C$ 552 round-trip on average, while Saturday is the most expensive at C$ 1,617, a difference of C$ 1,065. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport when travelling from Chicago O'Hare Intl Airport to Regina?

    Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 6h 10m, compared with 7h 34m via Denver Intl (DEN) and 8h 16m via Toronto Pearson Intl (YYZ).

  • What is the time difference between Chicago O'Hare Intl Airport and Regina?

    Regina is 1 hour behind Chicago O'Hare Intl Airport (Central Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Your guide to booking Chicago O'Hare Intl Airport to Regina flights

Get tips on when to book, when to fly, and what to know before your trip.
  • If your dates are flexible, aim for a Tuesday departure instead of Saturday. On this route, Tuesday flights average C$ 552 – about C$ 1,065 less than Saturday (66% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago O'Hare Intl Airport to Regina trip for October. Fares historically average C$ 474 round-trip in that month – typically C$ 1,142 less than the most expensive month, which is February (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Regina Airport.
    - Meridian Inn & Suites Regina Airport
    - Residence Inn by Marriott Regina

More options for your flight from Chicago to Regina

Complete your trip to Regina with a hotel stay or car rental

Car rentals in Regina
Hotels in Regina
Vacations in Regina