YQR - ORD

C$ 332 Find Cheap Flights from Regina to Chicago – Compare and Save

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Everything you should know

Cheapest round-trip
C$ 626
Typical prices: C$ 511-C$ 886
Air Canada
Tue 20/11Wed 28/11
YQR - ORD • 1 stop
Cheapest one-way flights
C$ 332
Typical prices: C$ 336-C$ 616
Air Canada
Mon 5/2
YQR - ORD • 1 stop
Direct flights
Not available
There are currently no direct flights between Regina and Chicago O'Hare Intl Airport. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
February
Cheapest • 35% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Calgary (YYC)
Cheapest • Avg C$ 539 (round-trip)
Minneapolis St Paul (MSP)
Shortest trip • 6h 37m (one-way)
Insights
Insights
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you enjoy your trip to Chicago O'Hare Intl Airport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Regina to Chicago (YQR-ORD)

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

Recent round-trip flight deals from Regina to Chicago

Fri, 20 Nov - Sat, 28 Nov
Air Canada Logo
5:00 a.m. - 3:38 p.m.YQR  Regina-ORD Chicago O'Hare Intl
10h 38m1 stop Toronto Pearson Intl
Air Canada Logo
4:40 p.m. - 11:27 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 47m1 stop Toronto Pearson Intl
C$ 626Air Canada
2 days ago
Tue, 24 Nov - Tue, 24 Nov
Air Canada Logo
5:00 a.m. - 1:13 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 13m1 stop Toronto Pearson Intl
Air Canada Logo
8:40 p.m. - 10:43 a.m.ORD  Chicago O'Hare Intl-YQR Regina
14h 03m1 stop Toronto Pearson Intl
C$ 626Air Canada
3+ days ago
Tue, 24 Nov - Tue, 24 Nov
Air Canada Logo
5:00 a.m. - 3:02 p.m.YQR  Regina-ORD Chicago O'Hare Intl
10h 02m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:40 p.m. - 10:43 a.m.ORD  Chicago O'Hare Intl-YQR Regina
14h 03m1 stop Toronto Pearson Intl
C$ 637Air Canada
3+ days ago
Fri, 20 Nov - Sat, 28 Nov
Air Canada Logo
5:00 a.m. - 3:00 p.m.YQR  Regina-ORD Chicago O'Hare Intl
10h 00m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
4:40 p.m. - 11:27 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 47m1 stop Toronto Pearson Intl
C$ 662Air Canada
3+ days ago
Fri, 20 Nov - Sat, 28 Nov
Air Canada Logo
5:00 a.m. - 3:00 p.m.YQR  Regina-ORD Chicago O'Hare Intl
10h 00m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
4:40 p.m. - 11:27 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 47m1 stop Toronto Pearson Intl
C$ 667Air Canada
2 days ago
Sun, 10 Jan - Sat, 20 Feb
Air Canada Logo
5:00 a.m. - 1:13 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 13m1 stop Toronto Pearson Intl
Air Canada Logo
4:30 p.m. - 11:27 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 57m1 stop Toronto Pearson Intl
C$ 676Air Canada
3+ days ago
Tue, 22 Dec - Tue, 5 Jan
Multiple Airlines Logo
11:50 a.m. - 10:08 a.m.YQR  Regina-ORD Chicago O'Hare Intl
22h 18m1 stop Minneapolis St Paul
Multiple Airlines Logo
6:21 a.m. - 6:40 p.m.ORD  Chicago O'Hare Intl-YQR Regina
12h 19m2 stops Denver Intl Minneapolis St Paul
C$ 713Multiple Airlines
3+ days ago
Thu, 24 Dec - Tue, 5 Jan
Air Canada Logo
5:00 a.m. - 3:38 p.m.YQR  Regina-ORD Chicago O'Hare Intl
10h 38m1 stop Toronto Pearson Intl
Air Canada Logo
4:30 p.m. - 11:27 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 57m1 stop Toronto Pearson Intl
C$ 724Air Canada
3+ days ago
Sun, 8 Nov - Sun, 15 Nov
United Airlines Logo
5:00 a.m. - 11:57 a.m.YQR  Regina-ORD Chicago O'Hare Intl
6h 57m1 stop Toronto Pearson Intl
United Airlines Logo
10:30 a.m. - 10:40 p.m.ORD  Chicago O'Hare Intl-YQR Regina
12h 10m2 stops Minneapolis St Paul Denver Intl
C$ 1,366United Airlines
3+ days ago
Tue, 22 Dec - Tue, 22 Dec
United Airlines Logo
5:00 a.m. - 6:50 p.m.YQR  Regina-ORD Chicago O'Hare Intl
13h 50m2 stops Toronto Pearson Intl Washington, D.C. Dulles Intl
United Airlines Logo
8:50 p.m. - 10:43 a.m.ORD  Chicago O'Hare Intl-YQR Regina
13h 53m1 stop Toronto Pearson Intl
C$ 1,397United Airlines
3+ days ago
Booking Insights

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

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from Regina to Chicago O'Hare Intl Airport typically range from C$ 511 to C$ 886. The lowest price found in the past 5 days was C$ 626, on Air Canada.

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

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Regina to Chicago O'Hare Intl Airport. It’s 21% cheaper than the average day, while Sunday is the most expensive, with prices 80% higher.

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

•February is the cheapest month to fly from Regina to Chicago O'Hare Intl Airport at C$ 415 round-trip.
•March (C$ 1,676) and April (C$ 1,113) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 303% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

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

Low season

February

Cheapest flight

C$ 332
Beat the crowds with an average 67% drop in traveller numbers.
The most popular month to fly with an average 106% increase in traveller numbers.
One-way flight from Regina to Chicago O'Hare Intl Airport

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

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

Find helpful answers about this route, including flight times, airports, airlines, and booking tips.

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

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

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

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

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

    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 Regina to Chicago O'Hare Intl Airport flight?

    Round-trip flights from Regina to Chicago O'Hare Intl Airport range from C$ 511 to C$ 886, with an average of C$ 639 over the past 12 months. Anything below C$ 511 counts as a good deal.

  • Have flight prices from Regina to Chicago O'Hare Intl Airport 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$ 626 to C$ 1,945. That means the highest observed fare was about 3x higher than the lowest one.

  • How are flight prices from Regina to Chicago O'Hare Intl Airport looking right now?

    One-way fares from Regina to Chicago O'Hare Intl Airport are currently lower than usual. Average one-way flight prices are about C$ 338, which is 37% below the typical average for this route.

  • What car rental options are available at Chicago O'Hare Intl Airport (ORD)?

    Chicago O'Hare Intl Airport (ORD) hosts 5 major car rental companies, with daily rates starting from around C$ 24 for economy cars. Top options include:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

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

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

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

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

    • Toronto Pearson Intl (YYZ) – 32% of one-stop connections
    • Calgary (YYC) – 27% of one-stop connections
    • Denver Intl (DEN) – 23% of one-stop connections
    • Minneapolis St Paul (MSP) – 18% of one-stop connections

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

    Yes. Flexible dates can save you up to 57% on flights from Regina to Chicago O'Hare Intl Airport. Tuesday is the cheapest departure day at C$ 507 round-trip on average, while Sunday is the most expensive at C$ 1,154, a difference of C$ 647.

    KAYAK's flexible dates feature shows options up to three 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 Regina to Chicago O'Hare Intl Airport?

    Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 6h 37m, compared with 8h 09m via Toronto Pearson Intl (YYZ) and 8h 11m via Denver Intl (DEN).

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

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

  • Which popular places can I visit in Chicago O'Hare Intl Airport?

    Some of the most popular sights in Chicago O'Hare Intl Airport are Magnificent Mile, River North, and Grant Park. These are among the most viewed places in Chicago O'Hare Intl Airport on KAYAK.

Your guide to booking Regina to Chicago O'Hare Intl Airport 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 and avoid flying on Sunday. On this route, Tuesday flights average C$ 507, about C$ 647 less than Sunday fares (56% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Regina to Chicago O'Hare Intl Airport trip for February. Fares historically average C$ 415 round-trip in that month – typically C$ 1,261 less than the most expensive month, which is March (based on the last 12 months).

More options for your flight from Regina to Chicago

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

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