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Cheap flights from Regina to Chicago 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 — CHI
25 Feb — 4 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Regina to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Regina to Chicago
Explore the most affordable flight options available from Regina to Chicago. 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 11/410:40 a.m.
YQR
-
MDW
1 stop7h 00m
Delta
Sat 18/49:46 a.m.
MDW
-
YQR
1 stop9h 35m
Delta
Deal found 25/1C$ 522
Mon 2/311:40 a.m.
YQR
-
MDW
1 stop7h 00m
Delta
Tue 3/37:20 p.m.
MDW
-
YQR
1 stop23h 11m
Delta
Deal found 25/1C$ 683
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 30/56:00 a.m.
YQR
-
MDW
2 stops11h 05m
WestJet
Thu 4/69:20 a.m.
MDW
-
YQR
2 stops12h 05m
WestJet
Deal found 26/1C$ 792
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
Sat 4/77:00 a.m.
YQR
-
MDW
2 stops10h 31m
WestJet
Wed 8/79:20 a.m.
MDW
-
YQR
1 stop8h 10m
WestJet
Deal found 24/1C$ 931
Mon 2/37:05 a.m.
YQR
-
MDW
2 stops11h 35m
WestJet
Tue 3/37:20 p.m.
MDW
-
YQR
2 stops30h 35m
WestJet
Deal found 24/1C$ 1,066

Find flight deals from Regina to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Regina (YQR) to Chicago (CHI). 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 Chicago 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 that are best for you.

Fly from

Regina

Fly to

Chicago

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 - MDW

YQRMDW

Regina

Sat 11/4

10:40 a.m.-6:40 p.m.

1 stop7h 00m

Chicago Midway

Sat 18/4

9:46 a.m.-6:21 p.m.

1 stop9h 35m

C$ 522

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 2/3

11:40 a.m.-6:40 p.m.

1 stop7h 00m

Chicago Midway

Tue 3/3

7:20 p.m.-6:31 p.m.

1 stop23h 11m

C$ 683

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 - MDW

YQRMDW

Regina

Sat 30/5

6:00 a.m.-6:31 p.m.

2 stops11h 31m

Chicago Midway

Thu 4/6

9:20 a.m.-5:20 p.m.

1 stop9h 00m

C$ 792

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 4/7

7:00 a.m.-6:31 p.m.

2 stops10h 31m

Chicago Midway

Wed 8/7

9:20 a.m.-4:30 p.m.

1 stop8h 10m

C$ 931

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/1

Showing 1-10 of 26 results
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Best time to book a flight from Regina to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

What’s the top layover airport for flights from Regina to Chicago?

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

Toronto (YYZ) – chosen by Cheapflights users on 56% of one-stop itineraries from Regina to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Regina to Chicago?

Average round-trip fare for 1-stop flights from Regina to Chicago, 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$ 324.

What’s the fastest layover option from Regina to Chicago?

Shortest average travel time for 1-stop one-way flights from Regina to Chicago, 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 37m.

Which airport typically offers the quickest layover for flights from Regina to Chicago?

Average layover duration for 1-stop one-way flights from Regina to Chicago, 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 Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 26 January 2026.
Read through reviews of airlines operating flights from Regina to Chicago, such as WestJet and Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,249 reviews
Check prices

Comfort

7.0

Boarding

7.4

Overall

7.2

Entertainment

6.1

Crew

7.9

Food

6.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
WestJet
7.2
Good
3,249 reviews
WestJet
7.2
Good
3,249 reviews
Check prices

Comfort

7.0

Boarding

7.4

Overall

7.2

Entertainment

6.1

Crew

7.9

Food

6.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
Air Canada
7.1
Good
10,656 reviews
WestJet
7.2
Good
3,249 reviews
Check prices

Comfort

7.0

Boarding

7.4

Overall

7.2

Entertainment

6.1

Crew

7.9

Food

6.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.

Related info for your journey

Find useful and relevant information for your journey from Regina to Chicago. 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?

    Regina (YQR) is the airport you will fly out of if you book a flight from Regina to Chicago. You should not have trouble finding flights to Chicago from Regina; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Regina airport to Chicago. It is only a 4.0 km journey to Regina (YQR) from Regina’s city centre.

  • How long is the flight from Regina to Chicago?

    WestJet, United Airlines, and Air Canada can get you from Regina to Chicago in just under 8h 01m. Your travel time can differ by up to 39m. There are 1588 km between Regina and Chicago. Both multi-stop and direct flights can be found to your destination and back.

  • What is the cheapest airline to fly from Regina to Chicago round-trip?

    Air Canada, at C$ 176, was found to be the cheapest airline from Regina to Chicago.. Air Canada is 68% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Regina to Chicago that include hotel bookings?

    Yes. In addition to deals on Regina to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Regina to Chicago?

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

  • Can I find deals for business class flights from Regina to Chicago?

    Yes. Cheapflights offers flight deals from Regina to Chicago 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

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Alternative routes for Regina to Chicago

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

Top airline flying from Regina to Chicago

Discover the top airline that operate flights from Regina to Chicago. 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 Chicago?

Deals for Regina to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Regina to Chicago?

Millions of users choose and trust Cheapflights to book the best flight deals from Regina to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Regina to Chicago with no change fees?

Certainly. Search results for flights to Chicago 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 Chicago become cheaper?

Of course! You can now track prices for flights from Regina to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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