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Cheap flights from Regina to Chicago from C$ 288

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 1/10. 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
4:15 p.m. - 4:40 p.m.
YQR
-
ORD
23h 25m
1 stop
WestJet Logo
2:20 p.m. - 11:25 p.m.
ORD
-
YQR
9h 05m
1 stop
C$ 462WestJet
Sat, 17 Oct - Fri, 20 Nov
WestJet Logo
8:20 p.m. - 4:40 p.m.
YQR
-
ORD
19h 20m
2 stops
WestJet Logo
2:20 p.m. - 12:55 a.m.
ORD
-
YQR
10h 35m
1 stop
C$ 496WestJet
Sat, 17 Oct - Fri, 20 Nov
United Airlines Logo
9:45 a.m. - 8:22 p.m.
YQR
-
ORD
9h 37m
1 stop
United Airlines Logo
8:40 a.m. - 10:41 p.m.
ORD
-
YQR
14h 01m
1 stop
C$ 519United Airlines
Sat, 17 Oct - Sun, 22 Nov
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
8:45 a.m. - 7:05 p.m.
ORD
-
YQR
11h 20m
2 stops
C$ 520Air Canada
Tue, 20 Oct - Sat, 24 Oct
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
8:45 a.m. - 7:05 p.m.
ORD
-
YQR
11h 20m
2 stops
C$ 521Air Canada
Tue, 20 Oct - Sat, 24 Oct
Air Canada Logo
5:45 a.m. - 8:12 p.m.
YQR
-
ORD
13h 27m
2 stops
Air Canada Logo
8:45 a.m. - 7:05 p.m.
ORD
-
YQR
11h 20m
2 stops
C$ 524Air Canada
Tue, 20 Oct - Sat, 24 Oct
Air Canada Logo
5:45 a.m. - 8:12 p.m.
YQR
-
ORD
13h 27m
2 stops
Air Canada Logo
8:45 a.m. - 7:05 p.m.
ORD
-
YQR
11h 20m
2 stops
C$ 526Air Canada
Tue, 20 Oct - Sat, 24 Oct
WestJet Logo
2:00 p.m. - 4:40 p.m.
YQR
-
ORD
25h 40m
1 stop
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 540WestJet
Fri, 14 Aug - Tue, 18 Aug
WestJet Logo
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
WestJet Logo
2:20 p.m. - 11:25 p.m.
ORD
-
YQR
9h 05m
1 stop
C$ 553WestJet
Thu, 15 Oct - Fri, 20 Nov
Delta Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
Delta Logo
9:30 a.m. - 7:21 p.m.
ORD
-
YQR
9h 51m
1 stop
C$ 560Delta
Thu, 15 Oct - Wed, 18 Nov

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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 Oct
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
24 Oct
ORD8:45 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR7:05 p.m.Regina
C$ 520
Air Canada
20 Oct
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
24 Oct
ORD8:45 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR7:05 p.m.Regina
C$ 521
Air Canada
20 Oct
YQR5:45 a.m.Regina
13h 27m
2 stops
ORD8:12 p.m.Chicago O'Hare Intl
24 Oct
ORD8:45 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR7:05 p.m.Regina
C$ 524

United Airlines flights from Regina to Chicago O'Hare Intl Airport

Our best United Airlines deals on Regina to Chicago O'Hare Intl Airport flight tickets
United Airlines
17 Oct
YQR9:45 a.m.Regina
10h 33m
1 stop
ORD9:18 p.m.Chicago O'Hare Intl
21 Nov
ORD8:40 a.m.Chicago O'Hare Intl
14h 01m
1 stop
YQR10:41 p.m.Regina
C$ 519
United Airlines
17 Aug
YQR9:45 a.m.Regina
13h 14m
1 stop
ORD11:59 p.m.Chicago O'Hare Intl
23 Aug
ORD7:00 a.m.Chicago O'Hare Intl
15h 30m
1 stop
YQR9:30 p.m.Regina
C$ 563
United Airlines
15 Oct
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
21 Nov
ORD8:40 a.m.Chicago O'Hare Intl
14h 01m
1 stop
YQR10:41 p.m.Regina
C$ 606

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 23 June 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 - ORD

YQRORD

Regina

Sat 17/10

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

1 stop23h 25m

Chicago O'Hare Intl

Fri 20/11

2:20 p.m.-11:25 p.m.

1 stop9h 05m

C$ 462

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 17/10

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

2 stops19h 20m

Chicago O'Hare Intl

Fri 20/11

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

1 stop10h 35m

C$ 496

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 17/10

9:45 a.m.-8:22 p.m.

1 stop9h 37m

Chicago O'Hare Intl

Sun 22/11

8:40 a.m.-10:41 p.m.

1 stop14h 01m

C$ 519

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 20/10

5:45 a.m.-2:55 p.m.

1 stop8h 10m

Chicago O'Hare Intl

Sat 24/10

8:45 a.m.-7:05 p.m.

2 stops11h 20m

C$ 520

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 20/10

5:45 a.m.-2:55 p.m.

1 stop8h 10m

Chicago O'Hare Intl

Sat 24/10

8:45 a.m.-7:05 p.m.

2 stops11h 20m

C$ 521

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 20/10

5:45 a.m.-8:12 p.m.

2 stops13h 27m

Chicago O'Hare Intl

Sat 24/10

8:45 a.m.-7:05 p.m.

2 stops11h 20m

C$ 524

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 20/10

5:45 a.m.-8:12 p.m.

2 stops13h 27m

Chicago O'Hare Intl

Sat 24/10

8:45 a.m.-7:05 p.m.

2 stops11h 20m

C$ 526

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 14/8

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

1 stop25h 40m

Chicago O'Hare Intl

Tue 18/8

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

1 stop8h 40m

C$ 540
Quickest round-trip

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 15/10

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

1 stop7h 05m

Chicago O'Hare Intl

Fri 20/11

2:20 p.m.-11:25 p.m.

1 stop9h 05m

C$ 553

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 15/10

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

1 stop8h 40m

Chicago O'Hare Intl

Wed 18/11

9:30 a.m.-7:21 p.m.

1 stop9h 51m

C$ 560

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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?

Air Canada, WestJet, and United Airlines are the most popular carriers 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

6h 56m

Direct flights

None
The fastest flight from Regina to Chicago O'Hare Intl Airport takes 6h 56m
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 6h 56m 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
Glenview
Waukegan
Rosemont
Des Plaines
Merrillville
Kenosha
Northbrook
Evanston
Tinley Park
Downers Grove
Great Lakes
Hammond
Harvey
Naperville
Munster
Harvard
Hoffman Estates
Elmhurst
DeKalb

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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