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Cheap flights from Regina to Chicago from C$ 284

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Regina to Chicago departing on 23/10. 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 Regina to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
2:00 p.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
25h 40m1 stop Calgary
WestJet Logo
5:30 p.m. - 11:20 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
C$ 536WestJet
Thu, 1 Oct - Mon, 5 Oct
Air Canada Logo
12:40 p.m. - 7:48 p.m.YQR  Regina-ORD Chicago O'Hare Intl
6h 08m1 stop Toronto Pearson Intl
Air Canada Logo
8:40 p.m. - 9:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
13h 30m1 stop Toronto Pearson Intl
C$ 545Air Canada
Mon, 12 Oct - Tue, 13 Oct
WestJet Logo
8:35 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
7h 05m1 stop Calgary
WestJet Logo
5:30 p.m. - 11:20 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
C$ 580WestJet
Thu, 27 Aug - Fri, 11 Sep
WestJet Logo
11:50 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
27h 50m2 stops Edmonton Calgary
WestJet Logo
5:30 p.m. - 11:20 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
C$ 581WestJet
Thu, 27 Aug - Fri, 11 Sep
WestJet Logo
11:50 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
27h 50m2 stops Edmonton Calgary
WestJet Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
C$ 588WestJet
Tue, 25 Aug - Fri, 28 Aug
WestJet Logo
4:15 p.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
23h 25m1 stop Calgary
WestJet Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
C$ 595WestJet
Tue, 25 Aug - Fri, 28 Aug
WestJet Logo
4:15 p.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
23h 25m1 stop Calgary
WestJet Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
C$ 596WestJet
Mon, 31 Aug - Thu, 3 Sep
WestJet Logo
11:50 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
27h 50m2 stops Edmonton Calgary
WestJet Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
C$ 616WestJet
Mon, 31 Aug - Thu, 3 Sep
WestJet Logo
11:50 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
27h 50m2 stops Edmonton Calgary
WestJet Logo
5:30 p.m. - 7:45 p.m.ORD  Chicago O'Hare Intl-YQR Regina
27h 15m2 stops Calgary Edmonton
C$ 617WestJet
Thu, 27 Aug - Fri, 11 Sep
WestJet Logo
11:50 a.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
27h 50m2 stops Edmonton Calgary
WestJet Logo
5:30 p.m. - 7:45 p.m.ORD  Chicago O'Hare Intl-YQR Regina
27h 15m2 stops Calgary Edmonton
C$ 623WestJet
Tue, 25 Aug - Fri, 28 Aug

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WestJet flights from Regina to Chicago O'Hare Intl Airport

Our best WestJet deals on Regina to Chicago O'Hare Intl Airport flight tickets
WestJet
1 Oct
YQR2:00 p.m.Regina
25h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
5 Oct
ORD5:30 p.m.Chicago O'Hare Intl
6h 50m
1 stop
YQR11:20 p.m.Regina
C$ 536
WestJet
27 Aug
YQR8:35 a.m.Regina
7h 05m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
11 Sep
ORD5:30 p.m.Chicago O'Hare Intl
6h 50m
1 stop
YQR11:20 p.m.Regina
C$ 580
WestJet
27 Aug
YQR11:50 a.m.Regina
27h 50m
2 stops
ORD4:40 p.m.Chicago O'Hare Intl
11 Sep
ORD5:30 p.m.Chicago O'Hare Intl
6h 50m
1 stop
YQR11:20 p.m.Regina
C$ 581

Delta flights from Regina to Chicago O'Hare Intl Airport

Our best Delta deals on Regina to Chicago O'Hare Intl Airport flight tickets
Delta
1 Oct
YQR6:00 a.m.Regina
11h 26m
2 stops
ORD6:26 p.m.Chicago O'Hare Intl
5 Oct
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
C$ 670
Delta
16 Sep
YQR10:45 a.m.Regina
8h 45m
2 stops
ORD8:30 p.m.Chicago O'Hare Intl
20 Sep
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
C$ 672

momondo Fare Finder

 
Customize your flight search to find flights from Regina to Chicago O'Hare Intl Airport 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 9 August 2026.
Use the filters below to find and compare flights from Regina to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 1/10

2:00 p.m.-4:40 p.m.

1 stop25h 40m

Chicago O'Hare Intl

Mon 5/10

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

1 stop6h 50m

C$ 536

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Mon 12/10

12:40 p.m.-7:48 p.m.

1 stop6h 08m

Chicago O'Hare Intl

Tue 13/10

8:40 p.m.-9:10 a.m.

1 stop13h 30m

C$ 545
Quickest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 27/8

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

1 stop7h 05m

Chicago O'Hare Intl

Fri 11/9

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

1 stop6h 50m

C$ 580

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 27/8

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

2 stops27h 50m

Chicago O'Hare Intl

Fri 11/9

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

1 stop6h 50m

C$ 581

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 25/8

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

2 stops27h 50m

Chicago O'Hare Intl

Fri 28/8

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

1 stop8h 40m

C$ 588

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 25/8

4:15 p.m.-4:40 p.m.

1 stop23h 25m

Chicago O'Hare Intl

Fri 28/8

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

1 stop8h 40m

C$ 595

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Mon 31/8

4:15 p.m.-4:40 p.m.

1 stop23h 25m

Chicago O'Hare Intl

Thu 3/9

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

1 stop8h 40m

C$ 596

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Mon 31/8

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

2 stops27h 50m

Chicago O'Hare Intl

Thu 3/9

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

1 stop8h 40m

C$ 616

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 27/8

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

2 stops27h 50m

Chicago O'Hare Intl

Fri 11/9

5:30 p.m.-7:45 p.m.

2 stops27h 15m

C$ 617

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 25/8

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

2 stops27h 50m

Chicago O'Hare Intl

Fri 28/8

5:30 p.m.-7:45 p.m.

2 stops27h 15m

C$ 623

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Regina to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

In general, February is the cheapest month to fly from Regina to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 305. The month of March is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Regina averaging around C$ 507.

When to book flights from Regina to Chicago O'Hare Intl Airport

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

Cheap Regina to Chicago O'Hare Intl Airport (YQR to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Regina to Chicago O'Hare Intl Airport

Fastest flight time

10h 45m

Direct flights

None
The fastest flight from Regina to Chicago O'Hare Intl Airport takes 10h 45m
There are no direct flights from Regina to Chicago O'Hare Intl Airport. There are no popular flight routes from Regina to Chicago O'Hare Intl Airport.
Search flight deals

Frequently asked questions about flying from Regina to Chicago O'Hare Intl Airport

  • How far is Regina to Chicago O'Hare Intl by plane?

    Regina and Chicago O'Hare Intl are 1586.9 km apart from one another. Typically, this will take 10h 45m by plane in normal conditions.

  • When did momondo last update prices for flights from Regina Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Regina Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Regina Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Regina Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Schaumburg
Crystal Lake
Glenview
Waukegan
Rosemont
Des Plaines
Merrillville
Kenosha
Northbrook
Skokie
Tinley Park
Evanston
Downers Grove
Great Lakes
Hammond
Naperville
Harvey
Munster
Hoffman Estates
Elmhurst

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Regina to Chicago. momondo saves you time and could save you money on your trip.

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

Flights from Regina to Chicago 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 Regina to Chicago?

momondo helps you find the best flight between Regina and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to Chicago from Regina are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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