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Cheap flights from Regina to Chicago from C$ 205

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 27/5. 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 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. - 11:20 p.m.
ORD
-
YQR
6h 50m
1 stop
C$ 464WestJet
Tue, 29 Sep - Mon, 5 Oct
United Airlines Logo
9:45 a.m. - 12:44 a.m.
YQR
-
ORD
13h 59m
1 stop
United Airlines Logo
7:05 a.m. - 9:30 p.m.
ORD
-
YQR
15h 25m
1 stop
C$ 518United Airlines
Wed, 17 Jun - Sat, 20 Jun
WestJet Logo
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
WestJet Logo
5:30 p.m. - 7:45 p.m.
ORD
-
YQR
27h 15m
2 stops
C$ 528WestJet
Tue, 29 Sep - Mon, 5 Oct
Air Canada Logo
5:45 a.m. - 1:23 p.m.
YQR
-
ORD
6h 38m
1 stop
Air Canada Logo
8:45 a.m. - 7:05 p.m.
ORD
-
YQR
11h 20m
2 stops
C$ 551Air Canada
Fri, 25 Sep - Sat, 26 Sep
Delta Logo
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
Delta Logo
5:30 a.m. - 5:20 p.m.
ORD
-
YQR
12h 50m
2 stops
C$ 588Delta
Fri, 5 Jun - Sun, 7 Jun
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
Multiple Airlines Logo
9:48 p.m. - 5:20 p.m.
ORD
-
YQR
20h 32m
2 stops
C$ 589Multiple Airlines
Mon, 8 Jun - Wed, 10 Jun
Delta Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
Delta Logo
12:27 p.m. - 5:20 p.m.
ORD
-
YQR
5h 53m
1 stop
C$ 591Delta
Mon, 8 Jun - Wed, 10 Jun
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
9:50 a.m. - 7:05 p.m.
ORD
-
YQR
10h 15m
1 stop
C$ 598Air Canada
Fri, 25 Sep - Sat, 26 Sep
Delta Logo
10:45 a.m. - 7:31 p.m.
YQR
-
ORD
7h 46m
1 stop
Delta Logo
12:27 p.m. - 5:20 p.m.
ORD
-
YQR
5h 53m
1 stop
C$ 599Delta
Sun, 7 Jun - Thu, 11 Jun
Delta Logo
10:45 a.m. - 11:57 p.m.
YQR
-
ORD
12h 12m
2 stops
Delta Logo
1:35 p.m. - 11:20 p.m.
ORD
-
YQR
10h 45m
2 stops
C$ 607Delta
Tue, 29 Sep - Mon, 5 Oct

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
25 Sep
YQR5:45 a.m.Regina
6h 38m
1 stop
ORD1:23 p.m.Chicago O'Hare Intl
26 Sep
ORD8:45 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR7:05 p.m.Regina
C$ 551
Air Canada
25 Sep
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
26 Sep
ORD9:50 a.m.Chicago O'Hare Intl
10h 15m
1 stop
YQR7:05 p.m.Regina
C$ 598
Air Canada
18 Aug
YQR6:00 a.m.Regina
7h 55m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
19 Aug
ORD9:50 a.m.Chicago O'Hare Intl
10h 20m
1 stop
YQR7:10 p.m.Regina
C$ 645

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 Jun
YQR9:45 a.m.Regina
13h 59m
1 stop
ORD12:44 a.m.Chicago O'Hare Intl
20 Jun
ORD7:05 a.m.Chicago O'Hare Intl
15h 25m
1 stop
YQR9:30 p.m.Regina
C$ 518
United Airlines
25 Sep
YQR5:45 a.m.Regina
6h 38m
1 stop
ORD1:23 p.m.Chicago O'Hare Intl
26 Sep
ORD12:52 p.m.Chicago O'Hare Intl
7h 13m
1 stop
YQR7:05 p.m.Regina
C$ 619
United Airlines
19 Jul
YQR9:45 a.m.Regina
13h 59m
1 stop
ORD12:44 a.m.Chicago O'Hare Intl
24 Jul
ORD12:55 p.m.Chicago O'Hare Intl
7h 15m
1 stop
YQR7:10 p.m.Regina
C$ 665

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 May 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

Tue 29/9

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

1 stop8h 40m

Chicago O'Hare Intl

Mon 5/10

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

1 stop6h 50m

C$ 464

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 17/6

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

1 stop13h 59m

Chicago O'Hare Intl

Sat 20/6

7:05 a.m.-9:30 p.m.

1 stop15h 25m

C$ 518

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 29/9

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

1 stop7h 05m

Chicago O'Hare Intl

Mon 5/10

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

2 stops27h 15m

C$ 528

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 25/9

5:45 a.m.-1:23 p.m.

1 stop6h 38m

Chicago O'Hare Intl

Sat 26/9

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

2 stops11h 20m

C$ 551

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 5/6

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

1 stop7h 05m

Chicago O'Hare Intl

Sun 7/6

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

2 stops12h 50m

C$ 588

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 8/6

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

1 stop8h 40m

Chicago O'Hare Intl

Wed 10/6

9:48 p.m.-5:20 p.m.

2 stops20h 32m

C$ 589

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 8/6

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

1 stop8h 40m

Chicago O'Hare Intl

Wed 10/6

12:27 p.m.-5:20 p.m.

1 stop5h 53m

C$ 591

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 25/9

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

1 stop8h 10m

Chicago O'Hare Intl

Sat 26/9

9:50 a.m.-7:05 p.m.

1 stop10h 15m

C$ 598
Quickest round-trip

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 7/6

10:45 a.m.-7:31 p.m.

1 stop7h 46m

Chicago O'Hare Intl

Thu 11/6

12:27 p.m.-5:20 p.m.

1 stop5h 53m

C$ 599

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 29/9

10:45 a.m.-11:57 p.m.

2 stops12h 12m

Chicago O'Hare Intl

Mon 5/10

1:35 p.m.-11:20 p.m.

2 stops10h 45m

C$ 607

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 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 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 38m

Direct flights

None
The fastest flight from Regina to Chicago O'Hare Intl Airport takes 6h 38m
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 38m 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
Des Plaines
Merrillville
Rosemont
Northbrook
Tinley Park
Evanston
Downers Grove
Skokie
Great Lakes
Wheeling
Hammond
Glenview
Harvey
Naperville
Munster
Hoffman Estates
Harvard
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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