ORD - YQR

$367 Find Cheap Flights from Chicago to Regina - Compare and Save

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
$376
Typical prices: $514-$751
WestJet
Mon 10/15Mon 10/22
ORD - YQR • 1 stop
Cheapest one-way
$448
Typical prices: $228-$724
Multiple Airlines
Wed 10/10
ORD - YQR • 3 stops
Nonstop 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 $551 (round-trip)
Minneapolis St Paul (MSP)
Shortest trip • 6h 10m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s 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)

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

Recent round-trip flight deals from Chicago to Regina

Thu, Oct 15 - Thu, Oct 22
WestJet Logo
5:30 pm - 11:20 pmORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
WestJet Logo
8:35 am - 4:40 pmYQR  Regina-ORD Chicago O'Hare Intl
7h 05m1 stop Calgary
$376WestJet
Thu, Oct 15 - Thu, Oct 22
WestJet Logo
5:30 pm - 11:20 pmORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
WestJet Logo
8:20 pm - 4:40 pmYQR  Regina-ORD Chicago O'Hare Intl
19h 20m2 stops Edmonton Calgary
$419WestJet
Thu, Oct 15 - Thu, Oct 22
WestJet Logo
5:30 pm - 11:15 amORD  Chicago O'Hare Intl-YQR Regina
18h 45m2 stops Calgary Edmonton
WestJet Logo
8:20 pm - 4:40 pmYQR  Regina-ORD Chicago O'Hare Intl
19h 20m2 stops Edmonton Calgary
$441WestJet
Wed, Oct 21 - Wed, Oct 28
Multiple Airlines Logo
2:30 pm - 9:30 pmORD  Chicago O'Hare Intl-YQR Regina
8h 00m1 stop Denver Intl
Multiple Airlines Logo
4:00 am - 1:13 pmYQR  Regina-ORD Chicago O'Hare Intl
8h 13m1 stop Toronto Pearson Intl
$481Multiple Airlines
Thu, Mar 4 - Sun, Mar 7
Multiple Airlines Logo
6:00 am - 10:41 pmORD  Chicago O'Hare Intl-YQR Regina
16h 41m1 stop Denver Intl
Multiple Airlines Logo
5:00 am - 1:13 pmYQR  Regina-ORD Chicago O'Hare Intl
8h 13m1 stop Toronto Pearson Intl
$481Multiple Airlines
Fri, Dec 25 - Tue, Jan 5
United Airlines Logo
3:40 pm - 10:57 pmORD  Chicago O'Hare Intl-YQR Regina
7h 17m1 stop Denver Intl
United Airlines Logo
10:45 am - 7:58 pmYQR  Regina-ORD Chicago O'Hare Intl
9h 13m1 stop Denver Intl
$483United Airlines
Wed, Oct 21 - Wed, Oct 28
Multiple Airlines Logo
7:00 am - 9:30 pmORD  Chicago O'Hare Intl-YQR Regina
15h 30m1 stop Denver Intl
Multiple Airlines Logo
4:00 am - 7:52 pmYQR  Regina-ORD Chicago O'Hare Intl
14h 52m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$489Multiple Airlines
Fri, Nov 20 - Tue, Nov 24
Air Canada Logo
8:40 pm - 10:43 amORD  Chicago O'Hare Intl-YQR Regina
14h 03m1 stop Toronto Pearson Intl
Air Canada Logo
5:00 am - 1:13 pmYQR  Regina-ORD Chicago O'Hare Intl
8h 13m1 stop Toronto Pearson Intl
$508Air Canada
Wed, Nov 18 - Tue, Nov 24
Air Canada Logo
10:15 am - 11:27 pmORD  Chicago O'Hare Intl-YQR Regina
13h 12m1 stop Toronto Pearson Intl
Air Canada Logo
5:00 am - 1:13 pmYQR  Regina-ORD Chicago O'Hare Intl
8h 13m1 stop Toronto Pearson Intl
$508Air Canada
Thu, Mar 25 - Sun, Mar 28
United Airlines Logo
2:18 pm - 9:41 pmORD  Chicago O'Hare Intl-YQR Regina
8h 23m1 stop Denver Intl
United Airlines Logo
9:45 am - 6:46 pmYQR  Regina-ORD Chicago O'Hare Intl
8h 01m1 stop Denver Intl
$647United Airlines
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 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 typically range from $514 to $751. The lowest price found in the past 5 days was $376, on WestJet.

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

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

Find deals

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

Low season

January

Cheapest flight

$376
Round-trip flight 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 answers about this route, including flight times, airports, airlines and booking tips.

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

    A nonstop flight from Chicago O'Hare Intl Airport to Regina takes 00m, covering 987 miles.

  • 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 $514 to $751, with an average of $609 over the past 12 months. Anything below $514 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 $376 to $1,078. That means the highest observed fare was about 3x higher than the lowest one.

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

    One-way fares from Chicago O'Hare Intl Airport to Regina are currently higher than usual. Average one-way flight prices are about $491, which is 56% above the typical average for this route.

  • 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 $21 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

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

    Yes. Flexible dates can save you up to 66% on flights from Chicago O'Hare Intl Airport to Regina. Tuesday is the cheapest departure day at $391 round-trip on average, while Saturday is the most expensive at $1,145, a difference of $754.

    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 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 and avoid flying on Saturday. On this route, Tuesday flights average $391, about $754 less than Saturday fares (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 $336 round-trip in that month - typically $809 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