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Cheap flights from Chicago to Regina from C$ 219

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 5/5. 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.
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
C$ 327WestJet
Wed, 27 May - Sat, 30 May
WestJet Logo
5:30 p.m. - 11:20 p.m.
ORD
-
YQR
6h 50m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
C$ 332WestJet
Wed, 27 May - Sat, 30 May
WestJet Logo
5:30 p.m. - 11:15 a.m.
ORD
-
YQR
18h 45m
2 stops
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
C$ 361WestJet
Wed, 27 May - Sat, 30 May
WestJet Logo
5:30 p.m. - 11:15 a.m.
ORD
-
YQR
18h 45m
2 stops
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
C$ 385WestJet
Wed, 27 May - Sat, 30 May
WestJet Logo
5:30 p.m. - 11:15 a.m.
ORD
-
YQR
18h 45m
2 stops
WestJet Logo
8:20 p.m. - 4:40 p.m.
YQR
-
ORD
19h 20m
2 stops
C$ 394WestJet
Wed, 27 May - Sat, 30 May
WestJet Logo
5:30 p.m. - 1:07 a.m.
ORD
-
YQR
8h 37m
1 stop
WestJet Logo
11:45 a.m. - 4:43 p.m.
YQR
-
ORD
27h 58m
1 stop
C$ 495WestJet
Wed, 24 Jun - Mon, 29 Jun
Multiple Airlines Logo
7:30 a.m. - 6:31 p.m.
ORD
-
YQR
12h 01m
1 stop
Multiple Airlines Logo
8:45 p.m. - 1:35 p.m.
YQR
-
ORD
15h 50m
1 stop
C$ 498Multiple Airlines
Sun, 22 Mar - Sun, 29 Mar
United Airlines Logo
7:00 a.m. - 9:51 p.m.
ORD
-
YQR
15h 51m
1 stop
United Airlines Logo
9:45 a.m. - 12:30 a.m.
YQR
-
ORD
13h 45m
1 stop
C$ 504United Airlines
Tue, 24 Mar - Tue, 31 Mar
WestJet Logo
5:30 p.m. - 1:07 a.m.
ORD
-
YQR
8h 37m
1 stop
WestJet Logo
10:05 a.m. - 4:43 p.m.
YQR
-
ORD
29h 38m
2 stops
C$ 522WestJet
Wed, 24 Jun - Mon, 29 Jun
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
WestJet Logo
9:05 p.m. - 4:40 p.m.
YQR
-
ORD
18h 35m
1 stop
C$ 524WestJet
Fri, 19 Jun - Sun, 21 Jun

WestJet flights from Chicago to Regina

Our best WestJet deals on Chicago to Regina flight tickets
WestJet
27 May
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
30 May
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 327
WestJet
27 May
ORD5:30 p.m.Chicago O'Hare Intl
6h 50m
1 stop
YQR11:20 p.m.Regina
30 May
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 332
WestJet
27 May
ORD5:30 p.m.Chicago O'Hare Intl
18h 45m
2 stops
YQR11:15 a.m.Regina
30 May
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 361

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
27 May
ORD8:45 a.m.Chicago O'Hare Intl
11h 22m
2 stops
YQR7:07 p.m.Regina
30 May
YQR5:45 a.m.Regina
13h 23m
2 stops
ORD8:08 p.m.Chicago O'Hare Intl
C$ 530
Air Canada
2 Mar
ORD8:40 p.m.Chicago O'Hare Intl
13h 59m
1 stop
YQR10:39 a.m.Regina
4 Mar
YQR5:00 a.m.Regina
8h 01m
1 stop
ORD1:01 p.m.Chicago O'Hare Intl
C$ 727
Air Canada
9 Apr
ORD6:40 p.m.Chicago O'Hare Intl
15h 52m
1 stop
YQR9:32 a.m.Regina
13 Apr
YQR5:00 a.m.Regina
7h 05m
1 stop
ORD1:05 p.m.Chicago O'Hare Intl
C$ 783

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 8 February 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

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 27/5

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

1 stop8h 40m

Regina

Sat 30/5

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

1 stop8h 40m

C$ 327

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 27/5

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

1 stop6h 50m

Regina

Sat 30/5

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

1 stop8h 40m

C$ 332

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 27/5

5:30 p.m.-11:15 a.m.

2 stops18h 45m

Regina

Sat 30/5

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

1 stop8h 40m

C$ 361

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 27/5

5:30 p.m.-11:15 a.m.

2 stops18h 45m

Regina

Sat 30/5

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

1 stop8h 40m

C$ 385

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 27/5

5:30 p.m.-11:15 a.m.

2 stops18h 45m

Regina

Sat 30/5

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

2 stops19h 20m

C$ 394

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 24/6

5:30 p.m.-1:07 a.m.

1 stop8h 37m

Regina

Mon 29/6

11:45 a.m.-4:43 p.m.

1 stop27h 58m

C$ 495

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sun 22/3

7:30 a.m.-6:31 p.m.

1 stop12h 01m

Regina

Sun 29/3

8:45 p.m.-1:35 p.m.

1 stop15h 50m

C$ 498

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 24/3

7:00 a.m.-9:51 p.m.

1 stop15h 51m

Regina

Tue 31/3

9:45 a.m.-12:30 a.m.

1 stop13h 45m

C$ 504

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 24/6

5:30 p.m.-1:07 a.m.

1 stop8h 37m

Regina

Mon 29/6

10:05 a.m.-4:43 p.m.

2 stops29h 38m

C$ 522

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 19/6

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

1 stop8h 40m

Regina

Sun 21/6

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

1 stop18h 35m

C$ 524

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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 airline that flies from Chicago to Regina?

United Airlines, Air Canada, and WestJet are the most popular carriers operating from Chicago to Regina

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

12h 01m

Direct flights

None
The fastest flight from Chicago to Regina takes 12h 01m
There are no direct flights from Chicago to Regina. There are no popular flight routes from Chicago to Regina.
Search flight deals

  • How far is Chicago to Regina by plane?

    There are 1611.7 km between Chicago and Regina. Flights usually cover this in 12h 01m, 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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