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Cheap flights from Regina to Chicago from C$ 180

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 10/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Regina to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 366WestJet
Thu, 7 May - Sun, 10 May
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 11:15 a.m.
ORD
-
YQR
18h 45m
2 stops
C$ 367WestJet
Sat, 30 May - Wed, 3 Jun
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 3:40 p.m.
ORD
-
YQR
23h 10m
1 stop
C$ 371WestJet
Sat, 30 May - Wed, 3 Jun
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 11:20 p.m.
ORD
-
YQR
6h 50m
1 stop
C$ 373WestJet
Sat, 30 May - Thu, 4 Jun
WestJet Logo
11:50 a.m. - 4:40 p.m.
YQR
-
ORD
27h 50m
2 stops
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 389WestJet
Thu, 7 May - Sun, 10 May
WestJet Logo
11:50 a.m. - 4:40 p.m.
YQR
-
ORD
27h 50m
2 stops
WestJet Logo
5:30 p.m. - 11:15 a.m.
ORD
-
YQR
18h 45m
2 stops
C$ 423WestJet
Thu, 7 May - Sun, 10 May
WestJet Logo
6:10 p.m. - 1:35 p.m.
YQR
-
ORD
19h 25m
2 stops
WestJet Logo
2:20 p.m. - 10:41 a.m.
ORD
-
YQR
21h 21m
1 stop
C$ 434WestJet
Thu, 5 Mar - Mon, 9 Mar
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 11:15 a.m.
ORD
-
YQR
18h 45m
2 stops
C$ 444WestJet
Sat, 30 May - Thu, 4 Jun
WestJet Logo
2:10 p.m. - 1:35 p.m.
YQR
-
ORD
23h 25m
1 stop
WestJet Logo
2:20 p.m. - 12:55 a.m.
ORD
-
YQR
11h 35m
1 stop
C$ 451WestJet
Thu, 5 Mar - Mon, 9 Mar
WestJet Logo
6:10 p.m. - 1:35 p.m.
YQR
-
ORD
19h 25m
2 stops
WestJet Logo
2:20 p.m. - 4:39 p.m.
ORD
-
YQR
27h 19m
2 stops
C$ 462WestJet
Thu, 5 Mar - Mon, 9 Mar

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
2 Mar
YQR5:00 a.m.Regina
8h 01m
1 stop
ORD1:01 p.m.Chicago O'Hare Intl
3 Mar
ORD1:55 p.m.Chicago O'Hare Intl
20h 44m
2 stops
YQR10:39 a.m.Regina
C$ 659
Air Canada
2 Mar
YQR5:00 a.m.Regina
8h 01m
1 stop
ORD1:01 p.m.Chicago O'Hare Intl
3 Mar
ORD8:40 p.m.Chicago O'Hare Intl
13h 59m
1 stop
YQR10:39 a.m.Regina
C$ 755
Air Canada
2 Mar
YQR5:00 a.m.Regina
8h 01m
1 stop
ORD1:01 p.m.Chicago O'Hare Intl
3 Mar
ORD6:00 p.m.Chicago O'Hare Intl
16h 39m
2 stops
YQR10:39 a.m.Regina
C$ 796

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
7 May
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
10 May
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
C$ 366
WestJet
30 May
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
3 Jun
ORD5:30 p.m.Chicago O'Hare Intl
18h 45m
2 stops
YQR11:15 a.m.Regina
C$ 367
WestJet
30 May
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
3 Jun
ORD5:30 p.m.Chicago O'Hare Intl
23h 10m
1 stop
YQR3:40 p.m.Regina
C$ 371

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 4 February 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

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 7/5

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

1 stop8h 40m

Chicago O'Hare Intl

Sun 10/5

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

1 stop8h 40m

C$ 366

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 30/5

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

1 stop8h 40m

Chicago O'Hare Intl

Wed 3/6

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

2 stops18h 45m

C$ 367

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 30/5

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

1 stop8h 40m

Chicago O'Hare Intl

Wed 3/6

5:30 p.m.-3:40 p.m.

1 stop23h 10m

C$ 371

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 30/5

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

1 stop8h 40m

Chicago O'Hare Intl

Thu 4/6

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

1 stop6h 50m

C$ 373

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 7/5

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

2 stops27h 50m

Chicago O'Hare Intl

Sun 10/5

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

1 stop8h 40m

C$ 389

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 7/5

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

2 stops27h 50m

Chicago O'Hare Intl

Sun 10/5

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

2 stops18h 45m

C$ 423

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/3

6:10 p.m.-1:35 p.m.

2 stops19h 25m

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-10:41 a.m.

1 stop21h 21m

C$ 434

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 30/5

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

1 stop8h 40m

Chicago O'Hare Intl

Thu 4/6

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

2 stops18h 45m

C$ 444

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/3

2:10 p.m.-1:35 p.m.

1 stop23h 25m

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-12:55 a.m.

1 stop11h 35m

C$ 451

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/3

6:10 p.m.-1:35 p.m.

2 stops19h 25m

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-4:39 p.m.

2 stops27h 19m

C$ 462

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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See travel insights to Chicago from

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 airline that flies from Regina to Chicago O'Hare Intl?

WestJet is the most popular carrier operating from Regina to Chicago O'Hare Intl

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

8h 01m

Direct flights

None
The fastest flight from Regina to Chicago O'Hare Intl Airport takes 8h 01m
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

  • 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 8h 01m 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
Air CanadaPriceFrom C$ 175Free CancellationRating
7.1
10,688 reviews
Search Air Canada flights

Travelling to a place near Chicago?

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

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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