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Cheap flights from Regina to Chicago O'Hare Intl Airport from C$ 230

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
YQR — ORD
25 Feb — 4 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Regina to O'Hare Intl

Enter your travel dates to find the best prices.

Cheapest flights from Regina to O'Hare Intl
Explore the most affordable flight options available from Regina to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 26 January 2026.

Sat 30/57:00 a.m.
YQR
-
ORD
1 stop8h 40m
WestJet
Thu 4/65:30 p.m.
ORD
-
YQR
1 stop18h 20m
WestJet
Deal found 26/1C$ 356
Sat 11/49:45 a.m.
YQR
-
ORD
1 stop8h 09m
United Airlines
Sat 18/410:49 a.m.
ORD
-
YQR
1 stop11h 41m
United Airlines
Deal found 25/1C$ 393
Mon 2/35:00 a.m.
YQR
-
ORD
1 stop8h 01m
Air Canada
Tue 3/38:40 p.m.
ORD
-
YQR
1 stop13h 59m
Air Canada
Deal found 24/1C$ 468
Sat 11/410:40 a.m.
YQR
-
ORD
1 stop8h 09m
Delta
Sat 18/47:00 a.m.
ORD
-
YQR
2 stops12h 21m
Delta
Deal found 25/1C$ 522
Sat 30/59:00 p.m.
YQR
-
ORD
3 stops21h 06m
Multiple Airlines
Thu 4/65:30 p.m.
ORD
-
YQR
2 stops18h 45m
Multiple Airlines
Deal found 26/1C$ 699
Sat 4/79:45 a.m.
YQR
-
ORD
1 stop11h 40m
United Airlines
Wed 8/77:15 a.m.
ORD
-
YQR
1 stop15h 21m
United Airlines
Deal found 24/1C$ 749
Sat 4/76:55 a.m.
YQR
-
ORD
1 stop8h 48m
WestJet
Wed 8/75:30 p.m.
ORD
-
YQR
2 stops24h 25m
WestJet
Deal found 24/1C$ 801

Find flight deals from Regina to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Regina (YQR) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 26 January 2026.

Round-trip from

C$ 356

One-way from

C$ 230

Popular in

March

Cheapest in

October

Average price

C$ 382
WestJet
  • WestJet
  • 30/5-4/6
  • 2 total stops
  • 27h 00m total
  • Regina to Chicago
Search Deals
WestJet
  • WestJet
  • 12/3
  • 1 total stop
  • 15h 50m total
  • Regina to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Regina to O'Hare Intl that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 26 January 2026.
Use the filters below to find and compare flights from Regina to Chicago O'Hare Intl Airport that are best for you.

Fly from

Regina

Fly to

O'Hare Intl

Route

Depart

Return

Price

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 30/5

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Thu 4/6

5:30 p.m.-11:15 a.m.

2 stops18h 45m

C$ 360

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 11/4

9:45 a.m.-6:54 p.m.

1 stop8h 09m

Chicago O'Hare Intl

Sat 18/4

10:49 a.m.-9:30 p.m.

1 stop11h 41m

C$ 393

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 2/3

5:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago O'Hare Intl

Tue 3/3

8:40 p.m.-10:39 a.m.

1 stop13h 59m

C$ 468

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 11/4

10:40 a.m.-7:49 p.m.

1 stop8h 09m

Chicago O'Hare Intl

Sat 18/4

7:00 a.m.-6:21 p.m.

2 stops12h 21m

C$ 522

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 30/5

9:00 p.m.-7:06 p.m.

3 stops21h 06m

Chicago O'Hare Intl

Thu 4/6

5:30 p.m.-11:15 a.m.

2 stops18h 45m

C$ 699

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 4/7

9:45 a.m.-10:25 p.m.

1 stop11h 40m

Chicago O'Hare Intl

Wed 8/7

7:15 a.m.-9:36 p.m.

1 stop15h 21m

C$ 749

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 12/3

8:45 p.m.-1:35 p.m.

1 stop15h 50m

C$ 230

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 6/3

10:45 a.m.-10:55 p.m.

1 stop12h 10m

C$ 236

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 10/4

9:45 a.m.-11:28 p.m.

1 stop12h 43m

C$ 236

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 18/3

9:45 a.m.-6:45 p.m.

1 stop8h 00m

C$ 236

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/1

Showing 1-10 of 14 results
1
2

Best time to book a flight from Regina to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Regina with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Regina to Chicago O'Hare Intl Airport

What’s the top layover airport for flights from Regina to Chicago O'Hare Intl Airport?

Share of one-stop round-trip flights from Regina to Chicago O'Hare Intl Airport chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YYZ) – chosen by Cheapflights users on 79% of one-stop itineraries from Regina to Chicago O'Hare Intl Airport on Cheapflights.

What’s the cheapest layover airport for flights from Regina to Chicago O'Hare Intl Airport?

Average round-trip fare for 1-stop flights from Regina to Chicago O'Hare Intl Airport, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 458.

What’s the fastest layover option from Regina to Chicago O'Hare Intl Airport?

Shortest average travel time for 1-stop one-way flights from Regina to Chicago O'Hare Intl Airport, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 5h 44m.

Which airport typically offers the quickest layover for flights from Regina to Chicago O'Hare Intl Airport?

Average layover duration for 1-stop one-way flights from Regina to Chicago O'Hare Intl Airport, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Minneapolis (MSP) offer the fastest connection on this route, with an average layover time of 1h 41m.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated 26 January 2026.
See what other customers who have flown with Air Canada from Regina to Chicago O'Hare Intl Airport have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,656 reviews
Check prices

Food

6.3

Entertainment

6.8

Overall

7.1

Crew

7.8

Boarding

7.3

Comfort

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍
Air Canada
7.1
Good
10,656 reviews
Air Canada
7.1
Good
10,656 reviews
Check prices

Food

6.3

Entertainment

6.8

Overall

7.1

Crew

7.8

Boarding

7.3

Comfort

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

YYZ - LAS

It's was great and the crew are very nice, captain has a smooth land on the runway 👍

Related info for your journey

Find useful and relevant information for your journey from Regina to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Regina to Chicago O'Hare Intl?

    Most people fly from Regina (YQR) if they book a flight from Regina to Chicago O'Hare Intl. On average, Regina has 0 outbound flights to Chicago O'Hare Intl per day from 1 airline. Regina is conveniently located just 4.0 km from Regina’s city centre.

  • How long is the flight from Regina to Chicago O'Hare Intl Airport?

    Airlines like WestJet, United Airlines, and Air Canada fly from Regina to Chicago O'Hare Intl Airport in about 8h 01m. The time it takes to get you to your destination can typically vary by up to 39m. Airlines will cover a distance of 1588 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What is the cheapest airline to fly from Regina to Chicago O'Hare Intl Airport round-trip?

    Cheapflights users have booked flights from Regina to Chicago O'Hare Intl Airport round-trip from C$ 176.

  • Can I find deals for flights from Regina to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Regina to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Regina to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Regina to O'Hare Intl.

  • Can I find deals for business class flights from Regina to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Regina to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Travelling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Evanston
Des Plaines
Skokie
Downers Grove
Elk Grove Village
Racine
Naperville
Bolingbrook
Romeoville

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Regina to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
Saskatoon to O'Hare Intl flights
Saskatoon to Midway flights

Top airline flying from Regina to O'Hare Intl

Discover the top airline that operate flights from Regina to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 26 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 176AverageC$ 1,462FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Regina to O'Hare Intl?

Cheapflights helps you search for flights from Regina to O'Hare Intl via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Regina to O'Hare Intl?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Regina to O'Hare Intl.

Can Cheapflights find flights from Regina to O'Hare Intl with no change fees?

Certainly. Search results for flights to O'Hare Intl from Regina shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Regina to O'Hare Intl become cheaper?

Not ready to book yet? You can track prices for flights from Regina to O'Hare Intl on Cheapflights with our Price Alert feature and get notified when better prices are available.

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