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Cheap flights from Chicago to Regina from C$ 330

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 9/6. 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

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Find the cheapest flights from Chicago to Regina

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:25 p.m. - 5:20 p.m.
ORD
-
YQR
23h 55m
1 stop
Multiple Airlines Logo
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
C$ 545Multiple Airlines
Fri, 5 Jun - Mon, 8 Jun
Multiple Airlines Logo
6:31 p.m. - 5:20 p.m.
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
10:45 a.m. - 5:24 p.m.
YQR
-
ORD
5h 39m
1 stop
C$ 586Multiple Airlines
Mon, 22 Jun - Mon, 29 Jun
United Airlines Logo
2:33 p.m. - 9:30 p.m.
ORD
-
YQR
7h 57m
1 stop
United Airlines Logo
9:45 a.m. - 10:49 p.m.
YQR
-
ORD
12h 04m
1 stop
C$ 641United Airlines
Sat, 6 Jun - Mon, 8 Jun
Air Canada Logo
8:40 p.m. - 9:05 a.m.
ORD
-
YQR
13h 25m
1 stop
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
C$ 645Air Canada
Fri, 19 Jun - Sun, 21 Jun
Multiple Airlines Logo
6:31 p.m. - 5:20 p.m.
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
9:05 p.m. - 7:50 p.m.
YQR
-
ORD
21h 45m
2 stops
C$ 664Multiple Airlines
Mon, 22 Jun - Mon, 29 Jun
United Airlines Logo
6:00 a.m. - 9:30 p.m.
ORD
-
YQR
16h 30m
1 stop
United Airlines Logo
9:45 a.m. - 11:19 p.m.
YQR
-
ORD
12h 34m
1 stop
C$ 667United Airlines
Tue, 23 Jun - Mon, 29 Jun
Air Canada Logo
8:45 a.m. - 7:05 p.m.
ORD
-
YQR
11h 20m
2 stops
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
C$ 670Air Canada
Tue, 20 Oct - Sat, 24 Oct
Multiple Airlines Logo
9:37 p.m. - 5:20 p.m.
ORD
-
YQR
20h 43m
2 stops
Multiple Airlines Logo
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
C$ 673Multiple Airlines
Fri, 5 Jun - Mon, 8 Jun
Air Canada Logo
8:40 p.m. - 9:05 a.m.
ORD
-
YQR
13h 25m
1 stop
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
C$ 678Air Canada
Fri, 19 Jun - Sun, 21 Jun
Multiple Airlines Logo
6:31 p.m. - 5:20 p.m.
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
10:45 a.m. - 8:03 a.m.
YQR
-
ORD
44h 18m
2 stops
C$ 681Multiple Airlines
Mon, 22 Jun - Mon, 29 Jun

Delta flights from Chicago to Regina

Our best Delta deals on Chicago to Regina flight tickets
Delta
18 Jun
ORD8:36 a.m.Chicago O'Hare Intl
9h 44m
1 stop
YQR5:20 p.m.Regina
21 Jun
YQR10:45 a.m.Regina
9h 40m
1 stop
ORD9:25 p.m.Chicago O'Hare Intl
C$ 749
Delta
19 Jun
ORD12:27 p.m.Chicago O'Hare Intl
5h 53m
1 stop
YQR5:20 p.m.Regina
21 Jun
YQR10:45 a.m.Regina
8h 46m
2 stops
ORD8:31 p.m.Chicago O'Hare Intl
C$ 763
Delta
5 Jun
ORD7:07 a.m.Chicago O'Hare Intl
11h 13m
2 stops
YQR5:20 p.m.Regina
8 Jun
YQR10:45 a.m.Regina
8h 46m
2 stops
ORD8:31 p.m.Chicago O'Hare Intl
C$ 770

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
19 Jun
ORD8:40 p.m.Chicago O'Hare Intl
13h 25m
1 stop
YQR9:05 a.m.Regina
21 Jun
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
C$ 645
Air Canada
20 Oct
ORD8:45 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR7:05 p.m.Regina
24 Oct
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
C$ 670
Air Canada
19 Jun
ORD8:40 p.m.Chicago O'Hare Intl
13h 25m
1 stop
YQR9:05 a.m.Regina
21 Jun
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
C$ 678

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 14 May 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

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 5/6

6:25 p.m.-5:20 p.m.

1 stop23h 55m

Regina

Mon 8/6

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

1 stop7h 05m

C$ 545

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 22/6

6:31 p.m.-5:20 p.m.

1 stop23h 49m

Regina

Mon 29/6

10:45 a.m.-5:24 p.m.

1 stop5h 39m

C$ 586

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 6/6

2:33 p.m.-9:30 p.m.

1 stop7h 57m

Regina

Mon 8/6

9:45 a.m.-10:49 p.m.

1 stop12h 04m

C$ 641

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 19/6

8:40 p.m.-9:05 a.m.

1 stop13h 25m

Regina

Sun 21/6

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

1 stop8h 10m

C$ 645

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 22/6

6:31 p.m.-5:20 p.m.

1 stop23h 49m

Regina

Mon 29/6

9:05 p.m.-7:50 p.m.

2 stops21h 45m

C$ 664

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 23/6

6:00 a.m.-9:30 p.m.

1 stop16h 30m

Regina

Mon 29/6

9:45 a.m.-11:19 p.m.

1 stop12h 34m

C$ 667
Quickest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 20/10

8:45 a.m.-7:05 p.m.

2 stops11h 20m

Regina

Sat 24/10

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

1 stop8h 10m

C$ 670

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 5/6

9:37 p.m.-5:20 p.m.

2 stops20h 43m

Regina

Mon 8/6

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

1 stop7h 05m

C$ 673

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 19/6

8:40 p.m.-9:05 a.m.

1 stop13h 25m

Regina

Sun 21/6

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

1 stop8h 10m

C$ 678

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 22/6

6:31 p.m.-5:20 p.m.

1 stop23h 49m

Regina

Mon 29/6

10:45 a.m.-8:03 a.m.

2 stops44h 18m

C$ 681

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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, January 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 January, then November is your next best option. Flight prices from Chicago to Regina during November average around C$ 188.

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

9h 44m

Direct flights

None
The fastest flight from Chicago to Regina takes 9h 44m
There are no direct flights from Chicago to Regina. There are no popular flight routes from Chicago to Regina.
Search flight deals

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 9h 44m, 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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