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Cheap flights from Illinois to Regina from C$ 287

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Regina departing on 25/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Illinois to Regina

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
WestJet Logo
11:50 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
27h 50m2 stops Edmonton Calgary
C$ 557WestJet
Sun, 27 Sep - Sun, 4 Oct
WestJet Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
WestJet Logo
11:40 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
28h 00m1 stop Calgary
C$ 593WestJet
Tue, 8 Sep - Wed, 9 Sep
WestJet Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
WestJet Logo
6:00 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 599WestJet
Tue, 1 Sep - Sat, 5 Sep
Multiple Airlines Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
Multiple Airlines Logo
5:45 a.m. - 2:55 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
C$ 603Multiple Airlines
Sun, 27 Sep - Sun, 4 Oct
Multiple Airlines Logo
11:05 a.m. - 10:50 a.m.ORD  Chicago O'Hare Intl-YQR Regina
24h 45m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl Calgary
Multiple Airlines Logo
5:45 a.m. - 1:23 p.m.YQR  Regina-ORD Chicago O'Hare Intl
6h 38m1 stop Toronto Pearson Intl
C$ 607Multiple Airlines
Sun, 27 Sep - Sun, 4 Oct
WestJet Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
WestJet Logo
9:05 p.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
18h 35m1 stop Calgary
C$ 614WestJet
Tue, 8 Sep - Wed, 9 Sep
Multiple Airlines Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
Multiple Airlines Logo
10:45 a.m. - 5:48 p.m.YQR  Regina-ORD Chicago O'Hare Intl
6h 03m1 stop Minneapolis St Paul
C$ 623Multiple Airlines
Mon, 7 Sep - Sun, 13 Sep
Multiple Airlines Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
Multiple Airlines Logo
5:45 a.m. - 2:55 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
C$ 624Multiple Airlines
Sun, 27 Sep - Sun, 4 Oct
Air Canada Logo
8:50 p.m. - 10:43 a.m.ORD  Chicago O'Hare Intl-YQR Regina
13h 53m1 stop Toronto Pearson Intl
Air Canada Logo
5:00 a.m. - 1:13 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 13m1 stop Toronto Pearson Intl
C$ 639Air Canada
Thu, 19 Nov - Tue, 24 Nov
Multiple Airlines Logo
11:05 a.m. - 10:50 a.m.ORD  Chicago O'Hare Intl-YQR Regina
24h 45m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl Calgary
Multiple Airlines Logo
8:20 p.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
19h 20m2 stops Edmonton Calgary
C$ 644Multiple Airlines
Sun, 27 Sep - Sun, 4 Oct

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Air Canada flights from Illinois to Regina

Our best Air Canada deals on Illinois to Regina flight tickets
Air Canada
19 Nov
ORD8:50 p.m.Chicago O'Hare Intl
13h 53m
1 stop
YQR10:43 a.m.Regina
24 Nov
YQR5:00 a.m.Regina
8h 13m
1 stop
ORD1:13 p.m.Chicago O'Hare Intl
C$ 639
Air Canada
19 Nov
ORD8:50 p.m.Chicago O'Hare Intl
13h 53m
1 stop
YQR10:43 a.m.Regina
24 Nov
YQR5:00 a.m.Regina
9h 52m
2 stops
ORD2:52 p.m.Chicago O'Hare Intl
C$ 652
Air Canada
23 Sep
ORD9:55 a.m.Chicago O'Hare Intl
10h 10m
1 stop
YQR7:05 p.m.Regina
30 Sep
YQR12:45 p.m.Regina
6h 03m
1 stop
ORD7:48 p.m.Chicago O'Hare Intl
C$ 670

Delta flights from Illinois to Regina

Our best Delta deals on Illinois to Regina flight tickets
Delta
19 Nov
ORD7:00 a.m.Chicago O'Hare Intl
12h 21m
2 stops
YQR7:21 p.m.Regina
24 Nov
YQR12:45 p.m.Regina
11h 14m
2 stops
ORD11:59 p.m.Chicago O'Hare Intl
C$ 850
Delta
19 Nov
ORD7:00 a.m.Chicago O'Hare Intl
12h 21m
2 stops
YQR7:21 p.m.Regina
25 Nov
YQR7:00 a.m.Regina
13h 25m
2 stops
ORD8:25 p.m.Chicago O'Hare Intl
C$ 861

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Regina 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, momondo users made 96,600 searches. Data last updated 13 August 2026.
Use the filters below to find and compare flights from Illinois to Regina that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Sun 27/9

5:30 p.m.-1:10 a.m.

1 stop8h 40m

Regina

Sun 4/10

11:50 a.m.-4:40 p.m.

2 stops27h 50m

C$ 557

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Tue 8/9

5:30 p.m.-1:10 a.m.

1 stop8h 40m

Regina

Wed 9/9

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

1 stop28h 00m

C$ 593

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Tue 1/9

5:30 p.m.-1:10 a.m.

1 stop8h 40m

Regina

Sat 5/9

6:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 599

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Sun 27/9

5:30 p.m.-1:10 a.m.

1 stop8h 40m

Regina

Sun 4/10

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

1 stop8h 10m

C$ 603

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Sun 27/9

11:05 a.m.-10:50 a.m.

3 stops24h 45m

Regina

Sun 4/10

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

1 stop6h 38m

C$ 607

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Tue 8/9

5:30 p.m.-1:10 a.m.

1 stop8h 40m

Regina

Wed 9/9

9:05 p.m.-4:40 p.m.

1 stop18h 35m

C$ 614
Quickest round-trip

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Mon 7/9

5:30 p.m.-1:10 a.m.

1 stop8h 40m

Regina

Sun 13/9

10:45 a.m.-5:48 p.m.

1 stop6h 03m

C$ 623

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Sun 27/9

5:30 p.m.-1:10 a.m.

1 stop8h 40m

Regina

Sun 4/10

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

1 stop8h 10m

C$ 624

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Thu 19/11

8:50 p.m.-10:43 a.m.

1 stop13h 53m

Regina

Tue 24/11

5:00 a.m.-1:13 p.m.

1 stop8h 13m

C$ 639

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Sun 27/9

11:05 a.m.-10:50 a.m.

3 stops24h 45m

Regina

Sun 4/10

8:20 p.m.-4:40 p.m.

2 stops19h 20m

C$ 644

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Illinois to Regina

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Regina?

In general, May is the cheapest month to fly from Illinois to Regina. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 0. If you’re not able to fly to Regina in May, then January is your next best option. Flight prices from Illinois to Regina during January average around C$ 0.

Cheap Illinois to Regina flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Regina

Fastest flight time

8h 40m

Direct flights

None
The fastest flight from Illinois to Regina takes 8h 40m
There are no direct flights from Illinois to Regina. There are no popular flight routes from Illinois to Regina.
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Frequently asked questions about flying from Illinois to Regina

  • When did momondo last update prices for flights from Illinois to Regina Airport?

    Prices for flights from Illinois to Regina Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Illinois to Regina Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Illinois to Regina Airport.

  • What documentation or ID do you need to fly to Regina Airport?

    The necessary travel and health documents for your Regina Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Travelling to a place near Regina?

Book flights to Regina if you plan to visit one of these locations
Moose Jaw

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Regina?

It is quick and easy to find Illinois to Regina flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Regina that suits you.

Can I find flights from Illinois to Regina with flexible booking policies on momondo?

Flights from Illinois to Regina with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Illinois to Regina?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Illinois to Regina.

I’m not ready to book a flight from Illinois to Regina right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Regina, momondo offers a useful price alert feature which will track prices for flights to Regina from Illinois and alert you when they change.

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