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Cheap flights from Chicago to Regina from C$ 248

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 8/5. 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
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
C$ 445WestJet
mar., 16 jun. - mar., 23 jun.
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
WestJet Logo
7:00 p.m. - 4:40 p.m.
YQR
-
ORD
20h 40m
1 stop
C$ 496WestJet
mar., 16 jun. - lun., 22 jun.
Multiple Airlines Logo
6:25 p.m. - 5:20 p.m.
ORD
-
YQR
23h 55m
1 stop
Multiple Airlines Logo
10:45 a.m. - 7:44 p.m.
YQR
-
ORD
7h 59m
1 stop
C$ 536Multiple Airlines
jue., 18 jun. - jue., 25 jun.
Multiple Airlines Logo
6:25 p.m. - 5:20 p.m.
ORD
-
YQR
23h 55m
1 stop
Multiple Airlines Logo
10:45 a.m. - 7:44 p.m.
YQR
-
ORD
7h 59m
1 stop
C$ 538Multiple Airlines
vie., 12 jun. - jue., 25 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. - 7:44 p.m.
YQR
-
ORD
7h 59m
1 stop
C$ 552Multiple Airlines
lun., 15 jun. - jue., 25 jun.
Multiple Airlines Logo
6:25 p.m. - 5:20 p.m.
ORD
-
YQR
23h 55m
1 stop
Multiple Airlines Logo
10:45 a.m. - 5:24 p.m.
YQR
-
ORD
5h 39m
1 stop
C$ 553Multiple Airlines
vie., 12 jun. - vie., 19 jun.
Delta Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
Delta Logo
10:45 a.m. - 5:02 p.m.
YQR
-
ORD
5h 17m
1 stop
C$ 567Delta
mar., 16 jun. - sáb., 20 jun.
Multiple Airlines Logo
6:25 p.m. - 5:20 p.m.
ORD
-
YQR
23h 55m
1 stop
Multiple Airlines Logo
10:45 a.m. - 5:29 p.m.
YQR
-
ORD
5h 44m
1 stop
C$ 568Multiple Airlines
vie., 12 jun. - lun., 22 jun.
United Airlines Logo
1:43 p.m. - 9:30 p.m.
ORD
-
YQR
8h 47m
1 stop
United Airlines Logo
9:45 a.m. - 9:23 p.m.
YQR
-
ORD
10h 38m
1 stop
C$ 571United Airlines
mar., 5 may. - sáb., 9 may.
United Airlines Logo
6:00 a.m. - 9:30 p.m.
ORD
-
YQR
16h 30m
1 stop
United Airlines Logo
9:45 a.m. - 12:44 a.m.
YQR
-
ORD
13h 59m
1 stop
C$ 574United Airlines
sáb., 13 jun. - sáb., 20 jun.

United Airlines flights from Chicago to Regina

Our best United Airlines deals on Chicago to Regina flight tickets
United Airlines
5 May
ORD1:43 p.m.Chicago O'Hare Intl
8h 47m
1 stop
YQR9:30 p.m.Regina
9 May
YQR9:45 a.m.Regina
10h 38m
1 stop
ORD9:23 p.m.Chicago O'Hare Intl
C$ 571
United Airlines
13 Jun
ORD6:00 a.m.Chicago O'Hare Intl
16h 30m
1 stop
YQR9:30 p.m.Regina
19 Jun
YQR9:45 a.m.Regina
13h 59m
1 stop
ORD12:44 a.m.Chicago O'Hare Intl
C$ 574
United Airlines
25 Apr
ORD7:00 a.m.Chicago O'Hare Intl
15h 30m
1 stop
YQR9:30 p.m.Regina
27 Apr
YQR9:45 a.m.Regina
12h 09m
1 stop
ORD10:54 p.m.Chicago O'Hare Intl
C$ 656

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
5 May
ORD8:45 a.m.Chicago O'Hare Intl
11h 22m
2 stops
YQR7:07 p.m.Regina
9 May
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
C$ 585
Air Canada
5 May
ORD8:45 a.m.Chicago O'Hare Intl
11h 22m
2 stops
YQR7:07 p.m.Regina
9 May
YQR5:45 a.m.Regina
13h 23m
2 stops
ORD8:08 p.m.Chicago O'Hare Intl
C$ 597
Air Canada
29 Apr
ORD6:40 p.m.Chicago O'Hare Intl
15h 52m
1 stop
YQR9:32 a.m.Regina
3 May
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
C$ 607

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 26 marzo 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

mar. 16/6

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

1 stop8h 40m

Regina

mar. 23/6

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

1 stop7h 05m

C$ 445

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

mar. 16/6

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

1 stop8h 40m

Regina

lun. 22/6

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

1 stop20h 40m

C$ 496

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

jue. 18/6

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

1 stop23h 55m

Regina

jue. 25/6

10:45 a.m.-7:44 p.m.

1 stop7h 59m

C$ 536

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

vie. 12/6

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

1 stop23h 55m

Regina

jue. 25/6

10:45 a.m.-7:44 p.m.

1 stop7h 59m

C$ 538

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

lun. 15/6

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

1 stop23h 49m

Regina

jue. 25/6

10:45 a.m.-7:44 p.m.

1 stop7h 59m

C$ 552

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

vie. 12/6

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

1 stop23h 55m

Regina

vie. 19/6

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

1 stop5h 39m

C$ 553
Quickest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

mar. 16/6

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

1 stop8h 40m

Regina

sáb. 20/6

10:45 a.m.-5:02 p.m.

1 stop5h 17m

C$ 567

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

vie. 12/6

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

1 stop23h 55m

Regina

lun. 22/6

10:45 a.m.-5:29 p.m.

1 stop5h 44m

C$ 568

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

mar. 5/5

1:43 p.m.-9:30 p.m.

1 stop8h 47m

Regina

sáb. 9/5

9:45 a.m.-9:23 p.m.

1 stop10h 38m

C$ 571

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

sáb. 13/6

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

1 stop16h 30m

Regina

sáb. 20/6

9:45 a.m.-12:44 a.m.

1 stop13h 59m

C$ 574

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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, Delta, 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

5h 53m

Direct flights

None
The fastest flight from Chicago to Regina takes 5h 53m
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 5h 53m, 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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