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Cheap flights from Regina to Chicago O'Hare Intl Airport from C$ 226

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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
YQR — ORD
3 Aug — 10 Aug1
1 adult

Cheap 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 29 July 2025.

Round-trip from

C$ 390

One-way from

C$ 226

Popular in

February

Cheapest in

April

Average price

C$ 546
WestJet
  • WestJet
  • 11/9-18/9
  • 2 total stops
  • 15h 19m total
  • Regina to Chicago
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WestJet
  • WestJet
  • 8/10
  • 1 total stop
  • 19h 08m total
  • Regina to Chicago
Search Deals
Highest demand for flights based on searches. 24% potential increase in price (C$ 308 potential increase over avg. RT price).
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Cheapest flight prices on average. 13% potential price decrease (C$ 113 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Regina to O'Hare Intl

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 29 July 2025.

Thu 11/96:55 a.m.YQR - ORD
1 stop8h 48mWestJet
Thu 18/95:30 p.m.ORD - YQR
1 stop6h 31mWestJet
Deal found 28/7C$ 390
Thu 20/115:00 a.m.YQR - ORD
1 stop8h 01mAir Canada
Tue 25/113:55 p.m.ORD - YQR
1 stop7h 24mAir Canada
Deal found 29/7C$ 407
Thu 11/911:45 a.m.YQR - ORD
3 stops23h 14mMultiple Airlines
Thu 18/912:54 p.m.ORD - YQR
3 stops23h 03mMultiple Airlines
Deal found 28/7C$ 797

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 29 July 2025.
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

Thu 11/9

6:55 a.m.-4:43 p.m.

1 stop8h 48m

Chicago O'Hare Intl

Thu 18/9

5:30 p.m.-11:01 p.m.

1 stop6h 31m

C$ 390

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 20/11

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

1 stop8h 01m

Chicago O'Hare Intl

Tue 25/11

3:55 p.m.-11:19 p.m.

1 stop7h 24m

C$ 407

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 11/9

11:45 a.m.-11:59 a.m.

3 stops23h 14m

Chicago O'Hare Intl

Thu 18/9

12:54 p.m.-10:57 a.m.

3 stops23h 03m

C$ 797

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 8/10

8:35 p.m.-4:43 p.m.

1 stop19h 08m

C$ 226

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 7/10

9:45 a.m.-6:25 p.m.

1 stop7h 40m

C$ 272

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 14/10

3:15 p.m.-11:36 a.m.

2 stops19h 21m

C$ 310

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 14/10

7:15 p.m.-9:13 a.m.

1 stop12h 58m

C$ 322

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

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 is the cheapest month to book a flight from Regina to Chicago O'Hare Intl Airport?

Currently, January is the cheapest month in which you can book a flight from Regina to Chicago O'Hare Intl Airport (average of C$ 261). Flying from Regina to Chicago O'Hare Intl Airport in March is currently the most expensive (average of C$ 352). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YQR to ORD?

Find hourly flight availability from Regina to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 29 July 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 31% on flights from Regina to Chicago O'Hare Intl Airport by exploring options for tickets in the afternoon.

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 65% 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$ 437.

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: 3h 43m.

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 Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 1h 50m.

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 29 July 2025.
See what other customers who have flown with United Airlines,WestJet, andAir 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.
United Airlines
7.4
Good
8,899 reviews
Check prices

Crew

8.1

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,899 reviews
United Airlines
7.4
Good
8,899 reviews
Check prices

Crew

8.1

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
WestJet
7.2
Good
2,973 reviews
United Airlines
7.4
Good
8,899 reviews
Check prices

Crew

8.1

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
9,822 reviews
United Airlines
7.4
Good
8,899 reviews
Check prices

Crew

8.1

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 3 airlines. Regina is conveniently located just 4.0 km from Regina’s city centre.

  • What are the cheapest airlines flying 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$ 390. Another airline that can offer you cheap pricing is Air Canada. These flights start at 44% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Regina to Chicago O'Hare Intl Airport one-way?

    The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as C$ 226. However, be on the lookout for offers from United Airlines and Air Canada, as they are both options that can get you from Regina to Chicago O'Hare Intl Airport for a low price.

  • 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.

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

    Currently, January is the cheapest month in which you can book a flight from Regina to Chicago O'Hare Intl Airport (average of C$ 261). Flying from Regina to Chicago O'Hare Intl Airport in March is currently the most expensive (average of C$ 352). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Elk Grove Village
Evanston
Des Plaines
Skokie
Downers Grove
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 3 airlines flying from Regina to O'Hare Intl

Discover the top 3 airlines 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 29 July 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 394AverageC$ 801FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 400AverageC$ 753FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 461AverageC$ 584FlexibilityNo cancel feeOn-timeN/A
Search Delta 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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