Find flights
When to book
Airlines
FAQs

Cheap flights from Regina to Chicago from C$ 319

YQR — CHI
23 Nov — 30 Nov1
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

Mon 7/125:00 a.m. -
1 stop8h 13m
Mon 14/128:50 p.m. -
1 stop13h 53m
Deal found 23/10C$ 617
Fri 4/1211:50 a.m. -
2 stops37h 04m
Fri 11/1211:48 a.m. -
1 stop6h 52m
Deal found 20/10C$ 637
Fri 13/115:00 a.m. -
1 stop10h 38m
Tue 17/118:40 p.m. -
1 stop14h 03m
Deal found 23/10C$ 689
Sat 14/1110:45 a.m. -
1 stop13h 14m
Wed 18/1110:55 a.m. -
1 stop11h 45m
Deal found 23/10C$ 739
Fri 20/115:00 a.m. -
1 stop10h 38m
Sat 28/114:40 p.m. -
1 stop6h 47m
Deal found 19/10C$ 756
Fri 4/125:00 a.m. -
1 stop10h 38m
Fri 11/124:30 p.m. -
1 stop6h 57m
Deal found 20/10C$ 760
Thu 12/1110:45 a.m. -
1 stop10h 45m
Wed 18/118:40 a.m. -
1 stop14h 00m
Deal found 23/10C$ 764
Fri 13/115:00 a.m. -
1 stop10h 38m
Wed 18/1110:15 a.m. -
1 stop13h 12m
Deal found 23/10C$ 788
Mon 7/1211:50 a.m. -
2 stops12h 06m
Mon 14/128:39 a.m. -
2 stops10h 01m
Deal found 23/10C$ 819

Find flight deals from Regina to Chicago

Round-trip from

C$ 637

One-way from

C$ 319

Popular in

March

Cheapest in

January

Average price

C$ 487
4/12-11/12
  • 4/12-11/12
  • 3 total stops
  • 43h 56m total
  • Regina to Chicago
Search Deals
8/12-31/12
  • 8/12-31/12
  • 2 total stops
  • 37h 04m total
  • Regina to Chicago
Search Deals
Highest demand for flights based on searches. 31% potential increase in price (C$ 501 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease (C$ 120 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2026
Search Deals

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 8/12

11:50 a.m.-12:54 a.m.

2 stops37h 04m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 319
Quickest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 8/12

5:00 a.m.-11:57 a.m.

1 stop6h 57m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 374

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 31/10

4:00 a.m.-11:57 a.m.

1 stop6h 57m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 594

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 30/10

4:00 a.m.-1:13 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 594

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 4/12

11:50 a.m.-12:54 a.m.

2 stops37h 04m

Chicago O'Hare Intl

Fri 11/12

11:48 a.m.-6:40 p.m.

1 stop6h 52m

C$ 637

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 31/10

4:00 a.m.-11:57 a.m.

1 stop6h 57m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 727

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 14/11

10:45 a.m.-11:59 p.m.

1 stop13h 14m

Chicago O'Hare Intl

Wed 18/11

10:55 a.m.-10:40 p.m.

1 stop11h 45m

C$ 739

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 19/1

10:45 a.m.-11:58 p.m.

1 stop13h 13m

Chicago O'Hare Intl

Thu 18/3

10:05 a.m.-10:22 p.m.

1 stop13h 17m

C$ 745

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 12/11

10:45 a.m.-9:30 p.m.

1 stop10h 45m

Chicago O'Hare Intl

Wed 18/11

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

1 stop14h 00m

C$ 764

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 19/1

5:00 a.m.-2:52 p.m.

2 stops9h 52m

Chicago O'Hare Intl

Thu 18/3

8:50 p.m.-9:36 a.m.

1 stop13h 46m

C$ 801

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/10

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

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, June is the cheapest month in which you can book a flight from Regina to Chicago (average of C$ 609). Flying from Regina to Chicago in March is currently the most expensive (average of C$ 1,649). 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?

Denver (DEN) – chosen by Cheapflights users on 39% 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$ 468.

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 Calgary (YYC) offer the fastest connection on this route, with an average layover time of 2h 00m.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Regina to Chicago, such as United Airlines and WestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.3
Good
10,420 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Food

6.7

Crew

8.1

Comfort

7.3

Overall

7.3

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
7.3
Good
10,420 reviews
United Airlines
7.3
Good
10,420 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Food

6.7

Crew

8.1

Comfort

7.3

Overall

7.3

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
7.3
Good
10,420 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Food

6.7

Crew

8.1

Comfort

7.3

Overall

7.3

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 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?

    United Airlines and Air Canada can get you from Regina to Chicago in just under 10h 38m. Your travel time can differ by up to 2h 36m. 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?

    United Airlines, at C$ 431, was found to be the cheapest airline from Regina to Chicago.. United Airlines is 46% 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.

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

    Currently, June is the cheapest month in which you can book a flight from Regina to Chicago (average of C$ 609). Flying from Regina to Chicago in March is currently the most expensive (average of C$ 1,649). 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

Top airline flying from Regina to Chicago

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 431AverageC$ 602FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.