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Cheap flights from Regina to Chicago from C$ 268

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 8/6. 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
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 515WestJet
Thu, 1 Oct - Mon, 5 Oct
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$ 516WestJet
Thu, 1 Oct - Mon, 5 Oct
WestJet Logo
8:20 p.m. - 4:40 p.m.
YQR
-
ORD
19h 20m
2 stops
WestJet Logo
5:30 p.m. - 11:20 p.m.
ORD
-
YQR
6h 50m
1 stop
C$ 569WestJet
Thu, 1 Oct - Mon, 5 Oct
WestJet Logo
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
WestJet Logo
5:30 p.m. - 11:15 a.m.
ORD
-
YQR
18h 45m
2 stops
C$ 570WestJet
Thu, 1 Oct - Mon, 5 Oct
Delta Logo
10:45 a.m. - 9:45 p.m.
YQR
-
MDW
10h 00m
2 stops
Delta Logo
1:00 p.m. - 11:20 p.m.
MDW
-
YQR
11h 20m
2 stops
C$ 601Delta
Thu, 22 Oct - Sat, 24 Oct
Delta Logo
7:00 a.m. - 6:37 p.m.
YQR
-
MDW
10h 37m
2 stops
Delta Logo
9:55 a.m. - 5:20 p.m.
MDW
-
YQR
8h 25m
1 stop
C$ 602Delta
Thu, 22 Oct - Sat, 24 Oct
Air Canada Logo
5:45 a.m. - 1:22 p.m.
YQR
-
ORD
6h 37m
1 stop
Air Canada Logo
8:40 p.m. - 9:05 a.m.
ORD
-
YQR
13h 25m
1 stop
C$ 631Air Canada
Tue, 23 Jun - Tue, 30 Jun
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
8:40 p.m. - 9:05 a.m.
ORD
-
YQR
13h 25m
1 stop
C$ 732Air Canada
Sat, 20 Jun - Sat, 27 Jun
Multiple Airlines Logo
4:15 p.m. - 9:40 a.m.
YQR
-
MDW
16h 25m
2 stops
Multiple Airlines Logo
10:25 a.m. - 12:35 a.m.
MDW
-
YQR
15h 10m
1 stop
C$ 762Multiple Airlines
Sat, 20 Jun - Sat, 27 Jun
Multiple Airlines Logo
6:00 a.m. - 9:40 a.m.
YQR
-
MDW
26h 40m
1 stop
Multiple Airlines Logo
10:25 a.m. - 12:35 a.m.
MDW
-
YQR
15h 10m
1 stop
C$ 772Multiple Airlines
Sat, 20 Jun - Sat, 27 Jun

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets
WestJet
1 Oct
YQR8:35 a.m.Regina
7h 05m
1 stop
ORD4:40 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$ 515
WestJet
1 Oct
YQR7:00 a.m.Regina
8h 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$ 516
WestJet
1 Oct
YQR8:20 p.m.Regina
19h 20m
2 stops
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$ 569

Air Canada flights from Regina to Chicago

Our best Air Canada deals on Regina to Chicago flight tickets
Air Canada
23 Jun
YQR5:45 a.m.Regina
6h 37m
1 stop
ORD1:22 p.m.Chicago O'Hare Intl
30 Jun
ORD8:40 p.m.Chicago O'Hare Intl
13h 25m
1 stop
YQR9:05 a.m.Regina
C$ 631
Air Canada
20 Jun
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
27 Jun
ORD8:40 p.m.Chicago O'Hare Intl
13h 25m
1 stop
YQR9:05 a.m.Regina
C$ 732
Air Canada
1 Oct
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
5 Oct
ORD8:45 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR7:05 p.m.Regina
C$ 820

momondo Fare Finder

 
Customize your flight search to find flights from Regina to Chicago 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 27 May 2026.
Use the filters below to find and compare flights from Regina to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 1/10

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

1 stop7h 05m

Chicago O'Hare Intl

Mon 5/10

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

1 stop8h 40m

C$ 515
Quickest round-trip

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 1/10

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$ 516

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 1/10

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

2 stops19h 20m

Chicago O'Hare Intl

Mon 5/10

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

1 stop6h 50m

C$ 569

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 1/10

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

1 stop7h 05m

Chicago O'Hare Intl

Mon 5/10

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

2 stops18h 45m

C$ 570

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 22/10

10:45 a.m.-9:45 p.m.

2 stops10h 00m

Chicago Midway

Sat 24/10

1:00 p.m.-11:20 p.m.

2 stops11h 20m

C$ 601

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 22/10

7:00 a.m.-6:37 p.m.

2 stops10h 37m

Chicago Midway

Sat 24/10

9:55 a.m.-5:20 p.m.

1 stop8h 25m

C$ 602

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 23/6

5:45 a.m.-1:22 p.m.

1 stop6h 37m

Chicago O'Hare Intl

Tue 30/6

8:40 p.m.-9:05 a.m.

1 stop13h 25m

C$ 631

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 20/6

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

1 stop8h 10m

Chicago O'Hare Intl

Sat 27/6

8:40 p.m.-9:05 a.m.

1 stop13h 25m

C$ 732

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 20/6

4:15 p.m.-9:40 a.m.

2 stops16h 25m

Chicago Midway

Sat 27/6

10:25 a.m.-12:35 a.m.

1 stop15h 10m

C$ 762

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 20/6

6:00 a.m.-9:40 a.m.

1 stop26h 40m

Chicago Midway

Sat 27/6

10:25 a.m.-12:35 a.m.

1 stop15h 10m

C$ 772

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

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 typical price of a round-trip flight between Regina and Chicago?

What is the cheapest month to fly to Chicago?

The month of October is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 279.

When to book flights from Regina to Chicago

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

Cheap Regina to Chicago (YQR to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Regina to Chicago

Fastest flight time

7h 05m

Direct flights

None
The fastest flight from Regina to Chicago takes 7h 05m
There are no direct flights from Regina to Chicago. There are no popular flight routes from Regina to Chicago.
Search flight deals

Frequently asked questions about flying from Regina to Chicago

  • How far is Regina to Chicago by plane?

    The distance between Regina and Chicago is about 1611.7 km. By plane, this route typically takes 7h 05m.

  • When did momondo last update prices for flights from Regina Airport to Chicago?

    Prices for flights from Regina Airport to Chicago were last updated today.

  • How old do you have to be to fly from Regina Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Regina Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Regina to Chicago?

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Munster

Why use momondo?

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

It is quick and easy to find Regina to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo allows you to filter the results for Regina to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Regina to Chicago?

Once all potential Regina to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport