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Cheap flights from Regina to Chicago from C$ 227

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 8/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Regina to Chicago

Cheap round-trip flights

WestJet Logo
6:55 a.m. - 4:43 p.m.YQR-ORD
8h 48m1 stop
WestJet Logo
5:30 p.m. - 11:01 p.m.ORD-YQR
6h 31m1 stop
C$ 391WestJet
Find Deal
Thu, 11 Sep - Thu, 18 Sep
Air Canada Logo
5:00 a.m. - 1:01 p.m.YQR-ORD
8h 01m1 stop
Air Canada Logo
3:55 p.m. - 11:19 p.m.ORD-YQR
7h 24m1 stop
C$ 409Air Canada
Find Deal
Thu, 20 Nov - Tue, 25 Nov
WestJet Logo
8:35 a.m. - 4:43 p.m.YQR-ORD
7h 08m1 stop
WestJet Logo
5:30 p.m. - 4:54 p.m.ORD-YQR
24h 24m2 stops
C$ 502WestJet
Find Deal
Thu, 11 Sep - Thu, 18 Sep
WestJet Logo
5:30 p.m. - 4:43 p.m.YQR-ORD
22h 13m2 stops
WestJet Logo
5:30 p.m. - 9:30 a.m.ORD-YQR
17h 00m2 stops
C$ 563WestJet
Find Deal
Thu, 11 Sep - Thu, 18 Sep
WestJet Logo
5:30 p.m. - 4:43 p.m.YQR-ORD
22h 13m2 stops
WestJet Logo
5:30 p.m. - 4:54 p.m.ORD-YQR
24h 24m3 stops
C$ 670WestJet
Find Deal
Thu, 11 Sep - Thu, 18 Sep
Logo
11:45 a.m. - 11:59 a.m.YQR-ORD
23h 14m3 stops
Logo
12:54 p.m. - 10:57 a.m.ORD-YQR
23h 03m3 stops
C$ 799
Find Deal
Thu, 11 Sep - Thu, 18 Sep
Air Canada Logo
5:00 a.m. - 1:01 p.m.YQR-ORD
8h 01m1 stop
Air Canada Logo
8:20 p.m. - 10:39 a.m.ORD-YQR
14h 19m1 stop
C$ 805Air Canada
Find Deal
Wed, 24 Dec - Sun, 28 Dec
Air Canada Logo
5:00 a.m. - 2:55 p.m.YQR-ORD
9h 55m2 stops
Air Canada Logo
8:20 p.m. - 10:39 a.m.ORD-YQR
14h 19m1 stop
C$ 812Air Canada
Find Deal
Wed, 24 Dec - Sun, 28 Dec
Air Canada Logo
5:00 a.m. - 2:55 p.m.YQR-ORD
9h 55m2 stops
Air Canada Logo
12:50 p.m. - 11:19 p.m.ORD-YQR
10h 29m2 stops
C$ 1,215Air Canada
Find Deal
Wed, 24 Dec - Sun, 28 Dec

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
11 Sep
YQR6:55 a.m.Regina
8h 48m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
18 Sep
ORD5:30 p.m.Chicago O'Hare Intl
6h 31m
1 stop
YQR11:01 p.m.Regina
C$ 391
Find similar
WestJet
11 Sep
YQR8:35 a.m.Regina
7h 08m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
18 Sep
ORD5:30 p.m.Chicago O'Hare Intl
24h 24m
2 stops
YQR4:54 p.m.Regina
C$ 502
Find similar
WestJet
11 Sep
YQR5:30 p.m.Regina
22h 13m
2 stops
ORD4:43 p.m.Chicago O'Hare Intl
18 Sep
ORD5:30 p.m.Chicago O'Hare Intl
17h 00m
2 stops
YQR9:30 a.m.Regina
C$ 563
Find similar

Air Canada flights from Regina to Chicago O'Hare Intl Airport

Our best Air Canada deals on Regina to Chicago O'Hare Intl Airport flight tickets
Air Canada
20 Nov
YQR5:00 a.m.Regina
8h 01m
1 stop
ORD1:01 p.m.Chicago O'Hare Intl
25 Nov
ORD3:55 p.m.Chicago O'Hare Intl
7h 24m
1 stop
YQR11:19 p.m.Regina
C$ 409
Find similar
Air Canada
24 Dec
YQR5:00 a.m.Regina
8h 01m
1 stop
ORD1:01 p.m.Chicago O'Hare Intl
28 Dec
ORD8:20 p.m.Chicago O'Hare Intl
14h 19m
1 stop
YQR10:39 a.m.Regina
C$ 805
Find similar
Air Canada
24 Dec
YQR5:00 a.m.Regina
9h 55m
2 stops
ORD2:55 p.m.Chicago O'Hare Intl
28 Dec
ORD8:20 p.m.Chicago O'Hare Intl
14h 19m
1 stop
YQR10:39 a.m.Regina
C$ 812
Find similar

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 30 July 2025.
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

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 11/9

6:55 a.m.-4:43 p.m.

1 stop8h 48m

Chicago O'Hare Intl

Thu 18/9

5:30 p.m.-11:01 p.m.

1 stop6h 31m

C$ 391

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 20/11

5:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago O'Hare Intl

Tue 25/11

3:55 p.m.-11:19 p.m.

1 stop7h 24m

C$ 409

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 11/9

8:35 a.m.-4:43 p.m.

1 stop7h 08m

Chicago O'Hare Intl

Thu 18/9

5:30 p.m.-4:54 p.m.

2 stops24h 24m

C$ 502

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 11/9

5:30 p.m.-4:43 p.m.

2 stops22h 13m

Chicago O'Hare Intl

Thu 18/9

5:30 p.m.-9:30 a.m.

2 stops17h 00m

C$ 563

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 11/9

5:30 p.m.-4:43 p.m.

2 stops22h 13m

Chicago O'Hare Intl

Thu 18/9

5:30 p.m.-4:54 p.m.

3 stops24h 24m

C$ 670

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 11/9

11:45 a.m.-11:59 a.m.

3 stops23h 14m

Chicago O'Hare Intl

Thu 18/9

12:54 p.m.-10:57 a.m.

3 stops23h 03m

C$ 799

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 24/12

5:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago O'Hare Intl

Sun 28/12

8:20 p.m.-10:39 a.m.

1 stop14h 19m

C$ 805

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 24/12

5:00 a.m.-2:55 p.m.

2 stops9h 55m

Chicago O'Hare Intl

Sun 28/12

8:20 p.m.-10:39 a.m.

1 stop14h 19m

C$ 812

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 24/12

5:00 a.m.-2:55 p.m.

2 stops9h 55m

Chicago O'Hare Intl

Sun 28/12

12:50 p.m.-11:19 p.m.

2 stops10h 29m

C$ 1,215

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 8/10

8:35 p.m.-4:43 p.m.

1 stop19h 08m

C$ 227

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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, April 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$ 475. The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Regina averaging around C$ 501.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as C$ 503. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Regina to Chicago O'Hare Intl Airport for around C$ 804.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the afternoon is the cheapest time of day to fly from Regina to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 460. Flying to Chicago O'Hare Intl Airport in the afternoon is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 666 on average. Flights to Chicago O'Hare Intl Airport from Regina at noon are generally more expensive because this time of day is more convenient for travellers’ schedules.

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

Best price found

C$ 227

Fastest flight time

7h 08m

Direct flights

None
The best one-way flight to Chicago O'Hare Intl Airport from Regina in the past 72 hours is C$ 227. The best round-trip flight deal from Regina to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 391.
The fastest flight from Regina to Chicago O'Hare Intl Airport takes 7h 08m
There are no direct flights from Regina to Chicago O'Hare Intl Airport. Popular non-direct route for this connection is Regina Airport - Chicago O'Hare Intl Airport.
Search flight deals

  • 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 7h 08m 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 many operators does momondo search for flights from Regina Airport to Chicago O'Hare Intl Airport?

  • 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.

  • What is the most popular airline from Regina to Chicago O'Hare Intl Airport?

Best airlines flying from Regina to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Regina to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 395Free CancellationRating
7.2
2,975 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 401Free CancellationRating
7.1
9,837 reviews
Search Air Canada flights
DeltaPriceFrom C$ 462Free CancellationRating
8.0
7,980 reviews
Search Delta flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Hoffman Estates
Lisle
Tinley Park
Glenview
Hammond
Naperville
Wheeling
Great Lakes
Munster
Des Plaines
Benton Harbor
Harvard
Merrillville
Schaumburg
Oak Brook
Elmhurst
Elk Grove Village
Bridgeview
Kenosha
Skokie

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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