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Cheap flights from Regina to Chicago from C$ 211

YQR — CHI
10 Oct — 17 Oct1
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

Tue 22/95:45 a.m. -
1 stop6h 38m
Wed 23/99:55 a.m. -
1 stop10h 10m
Deal found 7/9C$ 481
Tue 22/99:45 a.m. -
1 stop9h 37m
Wed 23/91:30 p.m. -
1 stop9h 00m
Deal found 9/9C$ 500
Sat 19/125:00 a.m. -
1 stop14h 58m
Sat 26/128:50 p.m. -
1 stop13h 53m
Deal found 6/9C$ 722
Sun 18/106:00 a.m. -
2 stops11h 00m
Thu 22/1012:27 p.m. -
1 stop5h 53m
Deal found 6/9C$ 1,040
Mon 7/94:15 p.m. -
2 stops17h 45m
Tue 8/93:20 p.m. -
1 stop10h 15m
Deal found 5/9C$ 1,442
Tue 22/910:45 a.m. -
1 stop5h 14m
Wed 23/912:29 p.m. -
2 stops13h 06m
Deal found 9/9C$ 1,526
Mon 7/92:15 p.m. -
1 stop16h 45m
Tue 8/95:53 p.m. -
1 stop16h 07m
Deal found 5/9C$ 1,620
Mon 7/97:00 a.m. -
2 stops10h 33m
Tue 8/99:29 a.m. -
2 stops16h 41m
Deal found 5/9C$ 1,690
Sun 18/1010:45 a.m. -
1 stop24h 02m
Thu 22/1012:27 p.m. -
1 stop5h 53m
Deal found 7/9C$ 2,484

Find flight deals from Regina to Chicago

Round-trip from

C$ 481

One-way from

C$ 211

Popular in

March

Cheapest in

November

Average price

C$ 875
Air Canada
  • Air Canada
  • 22/9-23/9
  • 2 total stops
  • 16h 48m total
  • Regina to Chicago
Search Deals
Air Canada
  • Air Canada
  • 22/9-31/12
  • 1 total stop
  • 8h 10m total
  • Regina to Chicago
Search Deals
Highest demand for flights based on searches. 34% potential increase in price (C$ 538 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease (C$ 110 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
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Cheapflights Fare Finder

 
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 Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 22/9

5:45 a.m.-1:23 p.m.

1 stop6h 38m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 232
Quickest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 10/10

12:40 p.m.-7:48 p.m.

1 stop6h 08m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 240

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 31/10

4:00 a.m.-7:52 p.m.

2 stops14h 52m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 251

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 10/10

11:40 a.m.-4:40 p.m.

1 stop28h 00m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 255

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 30/10

4:00 a.m.-7:58 p.m.

1 stop14h 58m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 273

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 30/10

11:50 a.m.-11:57 p.m.

2 stops11h 07m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 278

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 22/9

10:45 a.m.-8:30 p.m.

2 stops8h 45m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 278

ReginaChicago

YQR Regina - MDW Chicago Midway

YQRMDW

Regina

Tue 22/9

10:45 a.m.-6:19 p.m.

1 stop6h 34m

Chicago Midway

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 278

ReginaChicago

YQR Regina - MDW Chicago Midway

YQRMDW

Regina

Tue 6/10

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

2 stops11h 00m

Chicago Midway

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 290

ReginaChicago

YQR Regina - MDW Chicago Midway

YQRMDW

Regina

Tue 22/9

10:45 a.m.-10:44 p.m.

2 stops10h 59m

Chicago Midway

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 335

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

Showing 1-10 of 23 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

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, October is the cheapest month in which you can book a flight from Regina to Chicago (average of C$ 480). Flying from Regina to Chicago in March is currently the most expensive (average of C$ 1,624). 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’s the top layover airport for flights from Regina to Chicago?

Toronto (YYZ) – chosen by Cheapflights users on 36% of one-stop itineraries from Regina to Chicago on Cheapflights.

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

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of C$ 461.

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

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 6h 47m.

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

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 2h 04m.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Regina to Chicago, such as United Airlines,WestJet, andAir Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,194 reviews
Check prices

Food

6.7

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
United Airlines
7.4
Good
10,194 reviews
United Airlines
7.4
Good
10,194 reviews
Check prices

Food

6.7

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
WestJet
7.2
Good
3,445 reviews
United Airlines
7.4
Good
10,194 reviews
Check prices

Food

6.7

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
Air Canada
7.1
Good
11,608 reviews
United Airlines
7.4
Good
10,194 reviews
Check prices

Food

6.7

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!

Related info for your journey

  • 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?

    Air Canada, United Airlines, and Delta can get you from Regina to Chicago in just under 5h 34m. Your travel time can differ by up to 4h 03m. There are 1613 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, October is the cheapest month in which you can book a flight from Regina to Chicago (average of C$ 480). Flying from Regina to Chicago in March is currently the most expensive (average of C$ 1,624). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Regina to Chicago

Saskatoon to O'Hare Intl flights
Saskatoon to Midway flights
Saskatoon to St. Louis flights
Regina to O'Hare Intl flights

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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?

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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.

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