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Cheap flights from Regina to Chicago from C$ 223

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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
YQR — CHI
23 may. — 30 may.1
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 23 abril 2026.

vie. 5/67:00 a.m.
YQR
-
ORD
1 stop8h 40m
WestJet
dom. 7/65:30 p.m.
ORD
-
YQR
1 stop8h 40m
WestJet
Deal found 19/4C$ 392
mar. 5/59:45 a.m.
YQR
-
ORD
1 stop14h 13m
United Airlines
mar. 12/51:43 p.m.
ORD
-
YQR
1 stop8h 47m
United Airlines
Deal found 21/4C$ 395
vie. 8/58:35 a.m.
YQR
-
ORD
1 stop7h 05m
Multiple Airlines
mar. 12/59:37 p.m.
ORD
-
YQR
2 stops20h 43m
Multiple Airlines
Deal found 21/4C$ 422
vie. 5/68:35 a.m.
YQR
-
ORD
1 stop7h 05m
WestJet
vie. 12/65:30 p.m.
ORD
-
YQR
1 stop20h 15m
WestJet
Deal found 21/4C$ 425
dom. 31/59:45 a.m.
YQR
-
ORD
1 stop13h 59m
United Airlines
mié. 3/66:00 a.m.
ORD
-
YQR
1 stop16h 30m
United Airlines
Deal found 21/4C$ 428
lun. 11/58:35 a.m.
YQR
-
ORD
1 stop7h 05m
Multiple Airlines
mar. 19/59:37 p.m.
ORD
-
YQR
2 stops20h 43m
Multiple Airlines
Deal found 21/4C$ 429
vie. 8/57:00 a.m.
YQR
-
ORD
1 stop8h 40m
Delta
mar. 12/58:42 a.m.
ORD
-
YQR
1 stop9h 38m
Delta
Deal found 21/4C$ 464
lun. 11/58:35 a.m.
YQR
-
ORD
1 stop7h 05m
Multiple Airlines
vie. 22/56:12 p.m.
ORD
-
YQR
1 stop24h 08m
Multiple Airlines
Deal found 21/4C$ 466
lun. 11/58:35 a.m.
YQR
-
ORD
1 stop7h 05m
Multiple Airlines
mié. 20/58:00 a.m.
ORD
-
YQR
2 stops34h 20m
Multiple Airlines
Deal found 21/4C$ 467
mié. 6/510:45 a.m.
YQR
-
MDW
1 stop6h 51m
Delta
lun. 11/59:23 a.m.
MDW
-
YQR
1 stop8h 57m
Delta
Deal found 21/4C$ 478
mar. 5/510:45 a.m.
YQR
-
MDW
2 stops10h 43m
Delta
sáb. 9/59:22 a.m.
MDW
-
YQR
2 stops8h 58m
Delta
Deal found 21/4C$ 479
mié. 6/56:00 a.m.
YQR
-
MDW
2 stops10h 58m
Delta
vie. 8/51:22 p.m.
MDW
-
YQR
2 stops10h 58m
Delta
Deal found 21/4C$ 490

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 23 abril 2026.

Round-trip from

C$ 392

One-way from

C$ 223

Popular in

March

Cheapest in

October

Average price

C$ 512
WestJet
  • WestJet
  • 5/6-7/6
  • 2 total stops
  • 17h 20m total
  • Regina to Chicago
Search Deals
WestJet
  • WestJet
  • 3/6
  • 1 total stop
  • 8h 40m total
  • Regina to Chicago
Search Deals
Highest demand for flights based on searches. 34% potential increase in price (C$ 440 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease (C$ 78 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 23 abril 2026.
Use the filters below to find and compare flights from Regina to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ReginaChicago

YQR - ORD

YQRORD

Regina

mar. 2/6

9:45 a.m.-10:49 p.m.

1 stop12h 04m

Chicago O'Hare Intl

sáb. 6/6

6:00 a.m.-9:30 p.m.

1 stop16h 30m

C$ 453

ReginaChicago

YQR - ORD

YQRORD

Regina

dom. 31/5

9:45 a.m.-12:44 a.m.

1 stop13h 59m

Chicago O'Hare Intl

mié. 3/6

6:00 a.m.-9:30 p.m.

1 stop16h 30m

C$ 453

ReginaChicago

YQR - ORD

YQRORD

Regina

jue. 7/5

5:45 a.m.-2:55 p.m.

1 stop8h 10m

Chicago O'Hare Intl

mar. 12/5

1:43 p.m.-9:30 p.m.

1 stop8h 47m

C$ 470

ReginaChicago

YQR - ORD

YQRORD

Regina

mar. 5/5

10:45 a.m.-8:40 p.m.

2 stops8h 55m

Chicago O'Hare Intl

jue. 7/5

2:00 p.m.-11:20 p.m.

2 stops10h 20m

C$ 479

ReginaChicago

YQR - ORD

YQRORD

Regina

mié. 6/5

10:45 a.m.-7:52 p.m.

1 stop8h 07m

Chicago O'Hare Intl

sáb. 9/5

7:00 a.m.-5:20 p.m.

2 stops11h 20m

C$ 479

ReginaChicago

YQR - ORD

YQRORD

Regina

vie. 8/5

7:00 a.m.-6:05 p.m.

2 stops10h 05m

Chicago O'Hare Intl

dom. 10/5

8:42 a.m.-5:20 p.m.

1 stop9h 38m

C$ 479

ReginaChicago

YQR - MDW

YQRMDW

Regina

mié. 6/5

10:45 a.m.-6:36 p.m.

1 stop6h 51m

Chicago Midway

mar. 12/5

1:22 p.m.-1:10 a.m.

2 stops12h 48m

C$ 479

ReginaChicago

YQR - MDW

YQRMDW

Regina

jue. 7/5

7:00 a.m.-6:33 p.m.

2 stops10h 33m

Chicago Midway

sáb. 9/5

9:23 a.m.-5:20 p.m.

1 stop8h 57m

C$ 479

ReginaChicago

YQR - ORD

YQRORD

Regina

mié. 3/6

5:45 a.m.-1:25 p.m.

1 stop6h 40m

Chicago O'Hare Intl

mié. 10/6

8:20 p.m.-9:05 a.m.

1 stop13h 45m

C$ 486

ReginaChicago

YQR - MDW

YQRMDW

Regina

mié. 6/5

6:00 a.m.-5:58 p.m.

2 stops10h 58m

Chicago Midway

vie. 8/5

1:22 p.m.-11:20 p.m.

2 stops10h 58m

C$ 490

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/4

Showing 1-10 of 27 resultsSorted by cheapest first
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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 is the cheapest month to book a flight from Regina to Chicago?

Currently, August is the cheapest month in which you can book a flight from Regina to Chicago (average of C$ 214). Flying from Regina to Chicago in February is currently the most expensive (average of C$ 1,074). 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.

How much does it cost to fly round-trip 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.

Calgary (YYC) – chosen by Cheapflights users on 49% 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$ 323.

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 34m.

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 Denver (DEN) offer the fastest connection on this route, with an average layover time of 1h 56m.

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 23 abril 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
3,324 reviews
Check prices

Boarding

7.4

Overall

7.2

Food

6.2

Entertainment

6.1

Comfort

7.0

Crew

7.9

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
3,324 reviews
WestJet
7.2
Good
3,324 reviews
Check prices

Boarding

7.4

Overall

7.2

Food

6.2

Entertainment

6.1

Comfort

7.0

Crew

7.9

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
10,957 reviews
WestJet
7.2
Good
3,324 reviews
Check prices

Boarding

7.4

Overall

7.2

Food

6.2

Entertainment

6.1

Comfort

7.0

Crew

7.9

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 0 airlines have 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?

    United Airlines and Delta can get you from Regina to Chicago in just under 8h 55m. Your travel time can differ by up to 3h 09m. There are 1588 km between Regina and Chicago. Both multi-stop and direct flights can be found to your destination and back.

  • 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.

  • What is the cheapest month to book a flight from Regina to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Regina to Chicago (average of C$ 214). Flying from Regina to Chicago in February is currently the most expensive (average of C$ 1,074). 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

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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.
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Fly with Cheapflights

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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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