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Cheap flights from Chicago to Regina from C$ 259

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Regina departing on 28/9. 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 Chicago to Regina

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
5:30 p.m. - 11:20 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 40m1 stop Calgary
C$ 479WestJet
Mon, 28 Sep - Mon, 5 Oct
WestJet Logo
5:30 p.m. - 11:20 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 40m1 stop Calgary
C$ 480WestJet
Mon, 28 Sep - Mon, 5 Oct
WestJet Logo
5:30 p.m. - 11:20 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 40m1 stop Calgary
C$ 484WestJet
Mon, 28 Sep - Mon, 5 Oct
Multiple Airlines Logo
5:30 p.m. - 11:20 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
Multiple Airlines Logo
10:45 a.m. - 12:23 a.m.YQR  Regina-ORD Chicago O'Hare Intl
36h 38m2 stops Minneapolis St Paul Denver Intl
C$ 488Multiple Airlines
Mon, 28 Sep - Mon, 5 Oct
Multiple Airlines Logo
5:30 p.m. - 11:20 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
Multiple Airlines Logo
10:45 a.m. - 12:23 a.m.YQR  Regina-ORD Chicago O'Hare Intl
36h 38m2 stops Minneapolis St Paul Denver Intl
C$ 490Multiple Airlines
Mon, 28 Sep - Mon, 5 Oct
WestJet Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
WestJet Logo
8:35 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
7h 05m1 stop Calgary
C$ 494WestJet
Mon, 28 Sep - Mon, 5 Oct
WestJet Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 40m1 stop Calgary
C$ 501WestJet
Sun, 27 Sep - Sun, 4 Oct
Multiple Airlines Logo
8:55 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
29h 15m2 stops Las Vegas Harry Reid Intl Calgary
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 40m1 stop Calgary
C$ 517Multiple Airlines
Mon, 28 Sep - Mon, 5 Oct
Multiple Airlines Logo
7:28 p.m. - 3:40 p.m.ORD  Chicago O'Hare Intl-YQR Regina
21h 12m2 stops Atlanta Hartsfield-Jackson Calgary
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 40m1 stop Calgary
C$ 519Multiple Airlines
Mon, 28 Sep - Mon, 5 Oct
WestJet Logo
5:30 p.m. - 10:50 a.m.ORD  Chicago O'Hare Intl-YQR Regina
18h 20m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 40m1 stop Calgary
C$ 526WestJet
Mon, 28 Sep - Mon, 5 Oct

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Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
3 Oct
ORD7:09 a.m.Chicago O'Hare Intl
7h 06m
1 stop
YQR1:15 p.m.Regina
9 Oct
YQR2:15 p.m.Regina
16h 45m
1 stop
ORD8:00 a.m.Chicago O'Hare Intl
C$ 774
Air Canada
15 Sep
ORD8:45 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR7:05 p.m.Regina
18 Sep
YQR12:40 p.m.Regina
6h 08m
1 stop
ORD7:48 p.m.Chicago O'Hare Intl
C$ 782
Air Canada
15 Sep
ORD9:55 a.m.Chicago O'Hare Intl
10h 10m
1 stop
YQR7:05 p.m.Regina
18 Sep
YQR5:45 a.m.Regina
8h 05m
1 stop
ORD2:50 p.m.Chicago O'Hare Intl
C$ 805

WestJet flights from Chicago to Regina

Our best WestJet deals on Chicago to Regina flight tickets
WestJet
28 Sep
ORD5:30 p.m.Chicago O'Hare Intl
6h 50m
1 stop
YQR11:20 p.m.Regina
5 Oct
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 479
WestJet
28 Sep
ORD5:30 p.m.Chicago O'Hare Intl
6h 50m
1 stop
YQR11:20 p.m.Regina
5 Oct
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 480
WestJet
28 Sep
ORD5:30 p.m.Chicago O'Hare Intl
6h 50m
1 stop
YQR11:20 p.m.Regina
5 Oct
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 484

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 15 August 2026.
Use the filters below to find and compare flights from Chicago to Regina that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Mon 28/9

5:30 p.m.-11:20 p.m.

1 stop6h 50m

Regina

Mon 5/10

7:00 a.m.-4:40 p.m.

1 stop8h 40m

C$ 479

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Mon 28/9

5:30 p.m.-11:20 p.m.

1 stop6h 50m

Regina

Mon 5/10

7:00 a.m.-4:40 p.m.

1 stop8h 40m

C$ 480

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Mon 28/9

5:30 p.m.-11:20 p.m.

1 stop6h 50m

Regina

Mon 5/10

7:00 a.m.-4:40 p.m.

1 stop8h 40m

C$ 484

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Mon 28/9

5:30 p.m.-11:20 p.m.

1 stop6h 50m

Regina

Mon 5/10

10:45 a.m.-12:23 a.m.

2 stops36h 38m

C$ 488

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Mon 28/9

5:30 p.m.-11:20 p.m.

1 stop6h 50m

Regina

Mon 5/10

10:45 a.m.-12:23 a.m.

2 stops36h 38m

C$ 490

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Mon 28/9

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

1 stop8h 40m

Regina

Mon 5/10

8:35 a.m.-4:40 p.m.

1 stop7h 05m

C$ 494

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

7:00 a.m.-4:40 p.m.

1 stop8h 40m

C$ 501

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Mon 28/9

8:55 p.m.-1:10 a.m.

2 stops29h 15m

Regina

Mon 5/10

7:00 a.m.-4:40 p.m.

1 stop8h 40m

C$ 517

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Mon 28/9

7:28 p.m.-3:40 p.m.

2 stops21h 12m

Regina

Mon 5/10

7:00 a.m.-4:40 p.m.

1 stop8h 40m

C$ 519

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Mon 28/9

5:30 p.m.-10:50 a.m.

1 stop18h 20m

Regina

Mon 5/10

7:00 a.m.-4:40 p.m.

1 stop8h 40m

C$ 526

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
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See travel insights to Regina from

How to get the cheapest flight ticket from Chicago 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 Chicago 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 Chicago to Regina during January average around C$ 0.

When to book flights from Chicago to Regina

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Regina according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Regina (CHI to YQR) flight deals and tips

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

Fastest flight time

8h 40m

Direct flights

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

  • How far is Chicago to Regina by plane?

    There are 1611.7 km between Chicago and Regina. Flights usually cover this in 8h 40m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Chicago to Regina Airport are updated daily.

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Regina for you.

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

Yes. All flights to Regina from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo provides multiple filters to help you find the best flight to Regina from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes momondo offers price alerts on flights to Regina from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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