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Cheap flights from Regina to Illinois from C$ 386

YQR — ORD
18 Nov — 25 Nov1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Regina to Illinois

Enter your travel dates to find the best prices.

Cheapest flights from Regina to Illinois

Fri 13/1111:50 a.m. -
1 stop6h 35m
Fri 20/1111:15 a.m. -
1 stop7h 25m
Deal found 16/10C$ 714
Fri 20/115:00 a.m. -
1 stop14h 58m
Sat 28/114:40 p.m. -
1 stop6h 47m
Deal found 18/10C$ 733
Fri 20/1111:50 a.m. -
1 stop7h 49m
Sat 28/113:47 p.m. -
2 stops9h 33m
Deal found 16/10C$ 752
Sun 8/115:00 a.m. -
1 stop8h 13m
Fri 13/118:45 a.m. -
1 stop14h 42m
Deal found 16/10C$ 1,001
Sun 8/116:45 a.m. -
2 stops13h 13m
Fri 13/118:45 a.m. -
1 stop14h 42m
Deal found 16/10C$ 1,068
Sun 1/1110:45 a.m. -
1 stop9h 20m
Wed 4/113:56 p.m. -
1 stop6h 44m
Deal found 19/10C$ 1,076

Find flight deals from Regina to Illinois

Round-trip from

C$ 714

One-way from

C$ 386

Popular in

March

Cheapest in

January

Average price

C$ 491
13/11-20/11
  • 13/11-20/11
  • 2 total stops
  • 14h 00m total
  • Regina to Illinois
Search Deals
Air Canada
  • Air Canada
  • 2/12-31/12
  • 1 total stop
  • 8h 13m total
  • Regina to Illinois
Search Deals
Highest demand for flights based on searches. 31% potential increase in price (C$ 509 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease (C$ 122 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Regina to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 3/12

5:00 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$ 386

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Wed 2/12

5:00 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$ 386

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 31/10

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$ 395

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 30/10

4:00 a.m.-5:43 p.m.

1 stop12h 43m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 429

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 20/11

5:00 a.m.-7:58 p.m.

1 stop14h 58m

Chicago O'Hare Intl

Sat 28/11

4:40 p.m.-11:27 p.m.

1 stop6h 47m

C$ 733

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 19/12

11:50 a.m.-6:29 p.m.

1 stop6h 39m

Chicago O'Hare Intl

Sat 26/12

12:33 p.m.-6:40 p.m.

1 stop6h 07m

C$ 786

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 13/11

9:10 p.m.-12:51 p.m.

2 stops15h 41m

Chicago O'Hare Intl

Fri 20/11

11:15 a.m.-6:40 p.m.

1 stop7h 25m

C$ 808

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 20/11

7:00 a.m.-6:30 p.m.

2 stops11h 30m

Chicago O'Hare Intl

Sat 28/11

3:47 p.m.-1:20 a.m.

2 stops9h 33m

C$ 989

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sun 1/11

10:45 a.m.-8:05 p.m.

1 stop9h 20m

Chicago O'Hare Intl

Wed 4/11

3:56 p.m.-10:40 p.m.

1 stop6h 44m

C$ 1,076

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sun 1/11

11:30 a.m.-7:15 p.m.

3 stops31h 45m

Chicago O'Hare Intl

Wed 4/11

4:36 p.m.-2:35 p.m.

2 stops21h 59m

C$ 1,080

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/10

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

Best time to book a flight from Regina to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Regina with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Regina to Illinois

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

Currently, June is the cheapest month in which you can book a flight from Regina to Illinois (average of C$ 613). Flying from Regina to Illinois in March is currently the most expensive (average of C$ 1,661). 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.

Reviews of airlines servicing Illinois

Check out reviews from past customers who have flown with United Airlines and WestJet from Regina to Illinois to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.3
Good
10,389 reviews
Check prices

Food

6.7

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.3

Comfort

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
10,389 reviews
United Airlines
7.3
Good
10,389 reviews
Check prices

Food

6.7

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.3

Comfort

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
3,448 reviews
United Airlines
7.3
Good
10,389 reviews
Check prices

Food

6.7

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.3

Comfort

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 Illinois?

    Regina (YQR), located 4.0 km from the city centre, is the airport you fly out of when you book flights from Regina to Illinois.

  • How long is the flight from Regina to Illinois?

    Air Canada and Delta can get you from Regina to Illinois in just under 6h 39m. Your travel time can differ by up to 8h 19m. Airlines will cover a distance of 1588 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Regina to Illinois 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 Illinois?

    Currently, June is the cheapest month in which you can book a flight from Regina to Illinois (average of C$ 613). Flying from Regina to Illinois in March is currently the most expensive (average of C$ 1,661). 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

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Top airline flying from Regina to Illinois

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 435AverageC$ 607FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

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Yes, Cheapflights offers price alerts on Regina to Illinois flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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