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Cheap flights from Regina to Illinois from C$ 244

YQR — ORD
4 Oct — 11 Oct1
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

Tue 22/99:45 a.m. -
1 stop7h 47m
Wed 23/95:55 a.m. -
1 stop16h 35m
Deal found 31/8C$ 420
Sat 21/1110:45 a.m. -
1 stop13h 14m
Sat 28/118:40 p.m. -
1 stop14h 03m
Deal found 1/9C$ 432
Sat 24/1010:45 a.m. -
1 stop9h 42m
Sat 31/109:59 a.m. -
1 stop9h 41m
Deal found 3/9C$ 457
Sat 3/105:40 a.m. -
1 stop6h 43m
Mon 5/108:40 p.m. -
1 stop13h 20m
Deal found 4/9C$ 489
Tue 6/1010:45 a.m. -
1 stop9h 42m
Fri 9/107:00 a.m. -
2 stops11h 20m
Deal found 31/8C$ 497
Sun 4/105:40 a.m. -
1 stop6h 43m
Tue 6/108:40 p.m. -
1 stop13h 20m
Deal found 4/9C$ 500
Tue 22/95:45 a.m. -
1 stop6h 38m
Wed 23/99:55 a.m. -
1 stop10h 10m
Deal found 3/9C$ 508
Sat 14/1110:45 a.m. -
1 stop7h 53m
Mon 16/118:40 p.m. -
1 stop14h 03m
Deal found 30/8C$ 514
Sun 4/108:20 p.m. -
2 stops19h 20m
Tue 6/105:30 p.m. -
1 stop8h 40m
Deal found 4/9C$ 516
Sat 3/1010:45 a.m. -
1 stop6h 14m
Mon 5/102:00 p.m. -
2 stops12h 10m
Deal found 4/9C$ 798
Sat 3/109:05 p.m. -
3 stops16h 30m
Mon 5/103:20 p.m. -
3 stops22h 15m
Deal found 4/9C$ 853
Sun 18/106:00 a.m. -
2 stops11h 00m
Thu 22/101:27 p.m. -
2 stops12h 43m
Deal found 1/9C$ 995

Find flight deals from Regina to Illinois

Round-trip from

C$ 420

One-way from

C$ 244

Popular in

March

Cheapest in

November

Average price

C$ 877
United Airlines
  • United Airlines
  • 22/9-23/9
  • 2 total stops
  • 24h 22m total
  • Regina to Illinois
Search Deals
Air Canada
  • Air Canada
  • 31/10-31/12
  • 2 total stops
  • 14h 52m total
  • Regina to Illinois
Search Deals
Highest demand for flights based on searches. 34% potential increase in price (C$ 540 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease (C$ 111 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
Search Deals

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

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$ 244

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$ 258

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Wed 7/10

9:45 a.m.-10:46 p.m.

1 stop12h 01m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 258

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 25/9

11:20 a.m.-1:23 p.m.

2 stops25h 03m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 266

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$ 268
Quickest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 31/10

10:50 a.m.-9:27 p.m.

1 stop9h 37m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 268

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 - MDW Chicago Midway

YQRMDW

Regina

Mon 19/10

10:45 a.m.-11:43 p.m.

2 stops35h 58m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 392

ReginaChicago

YQR Regina - MDW Chicago Midway

YQRMDW

Regina

Fri 2/10

7:00 a.m.-5:51 p.m.

3 stops33h 51m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 400

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 22/9

9:45 a.m.-6:32 p.m.

1 stop7h 47m

Chicago O'Hare Intl

Wed 23/9

5:55 a.m.-9:30 p.m.

1 stop16h 35m

C$ 420

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/9

Showing 1-10 of 26 resultsSorted by cheapest first
1
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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, October is the cheapest month in which you can book a flight from Regina to Illinois (average of C$ 480). Flying from Regina to Illinois in March is currently the most expensive (average of C$ 1,626). 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,WestJet, andAir Canada 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
7.4
Good
10,172 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.6

Boarding

7.7

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
7.4
Good
10,172 reviews
United Airlines
7.4
Good
10,172 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.6

Boarding

7.7

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
3,444 reviews
United Airlines
7.4
Good
10,172 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.6

Boarding

7.7

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!
Air Canada
7.1
Good
11,582 reviews
United Airlines
7.4
Good
10,172 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.6

Boarding

7.7

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?

    United Airlines and Delta can get you from Regina to Illinois in just under 7h 47m. Your travel time can differ by up to 4h 25m. 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, October is the cheapest month in which you can book a flight from Regina to Illinois (average of C$ 480). Flying from Regina to Illinois in March is currently the most expensive (average of C$ 1,626). 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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How does Cheapflights help users find flights from Regina to Illinois?

Deals for Regina to Illinois 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 Illinois?

Cheapflights simply makes it quick and affordable to book flights from Regina to Illinois by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

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

Yes, we can. To see specific flights from Regina to Illinois with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Regina to Illinois become cheaper?

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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