Which airport is the most popular layover for flights between Regina and Chicago?

Calgary (YYC) was the most common stop: 33% of momondo users choosing one-stop flights on this route connected there.

Which layover airport offers the lowest fares from Regina to Chicago?

Flights via Calgary (YYC) offer the lowest average round-trip price of C$ 373.

Which layover airport has the shortest travel time from Regina to Chicago?

Flights connecting via Denver (DEN) have the shortest average one-way travel time: 6h 20m.

What is the cheapest airline that flies from Regina to Chicago?

Air Canada and WestJet are the most popular carriers operating from Regina to Chicago

Which layover airport has the shortest connection time from Regina to Chicago?

Denver (DEN) has the shortest average layover time for this route: 1h 08m.

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 many operators does momondo search for flights from Regina Airport to Chicago?

There is 1 operator available for flights from Regina Airport to Chicago as of January 2026.

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.

C$ 182 Cheap Flights from Regina to Chicago in 2026

Q: What is the typical price of a round-trip flight between Regina and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from C$ 352 to C$ 426. The lowest price recently found on this route was C$ 274.

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Find the cheapest flights from Regina to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

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

YQR

ORD

7h 25m1 stop

2:20 p.m. - 10:32 a.m.

ORD

YQR

20h 12m2 stops

C$ 274WestJet

Mon, 23 Feb - Mon, 2 Mar

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

YQR

ORD

7h 25m1 stop

2:20 p.m. - 11:41 a.m.

ORD

YQR

21h 21m1 stop

C$ 281WestJet

Mon, 23 Feb - Mon, 2 Mar

10:45 a.m. - 9:29 p.m.

YQR

ORD

10h 44m1 stop

10:35 a.m. - 10:51 p.m.

ORD

YQR

12h 16m1 stop

C$ 302United Airlines

Tue, 24 Feb - Tue, 3 Mar

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

YQR

ORD

8h 48m1 stop

5:30 p.m. - 11:02 p.m.

ORD

YQR

6h 32m1 stop

C$ 334WestJet

Tue, 26 May - Sat, 30 May

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

YQR

ORD

22h 13m2 stops

5:30 p.m. - 11:02 p.m.

ORD

YQR

6h 32m1 stop

C$ 378WestJet

Tue, 26 May - Sat, 30 May

6:00 a.m. - 8:24 p.m.

YQR

ORD

13h 24m2 stops

8:55 a.m. - 4:30 p.m.

ORD

YQR

8h 35m2 stops

C$ 405Delta

Tue, 26 May - Sat, 30 May

11:35 a.m. - 11:56 p.m.

YQR

ORD

12h 21m2 stops

6:30 a.m. - 6:31 p.m.

ORD

YQR

12h 01m2 stops

C$ 412Delta

Tue, 24 Feb - Tue, 3 Mar

5:00 a.m. - 7:45 p.m.

YQR

ORD

14h 45m1 stop

8:40 p.m. - 10:39 a.m.

ORD

YQR

13h 59m1 stop

C$ 428Air Canada

Mon, 2 Mar - Tue, 3 Mar

5:00 a.m. - 7:45 p.m.

YQR

ORD

14h 45m1 stop

8:40 p.m. - 10:39 a.m.

ORD

YQR

13h 59m1 stop

C$ 430Air Canada

Mon, 2 Mar - Tue, 3 Mar

5:00 a.m. - 7:45 p.m.

YQR

ORD

14h 45m1 stop

12:50 p.m. - 10:39 a.m.

ORD

YQR

21h 49m2 stops

C$ 474Air Canada

Mon, 2 Mar - Tue, 3 Mar

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets

WestJet

23 Feb

YQR6:10 a.m.Regina

7h 25m

1 stop

ORD1:35 p.m.Chicago O'Hare Intl

2 Mar

ORD2:20 p.m.Chicago O'Hare Intl

20h 12m

2 stops

YQR10:32 a.m.Regina

C$ 274

WestJet

23 Feb

YQR6:10 a.m.Regina

7h 25m

1 stop

ORD1:35 p.m.Chicago O'Hare Intl

2 Mar

ORD2:20 p.m.Chicago O'Hare Intl

21h 21m

1 stop

YQR11:41 a.m.Regina

C$ 281

WestJet

26 May

YQR6:55 a.m.Regina

8h 48m

1 stop

ORD4:43 p.m.Chicago O'Hare Intl

30 May

ORD5:30 p.m.Chicago O'Hare Intl

6h 32m

1 stop

YQR11:02 p.m.Regina

C$ 334

United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets

United Airlines

24 Feb

YQR10:45 a.m.Regina

10h 44m

1 stop

ORD9:29 p.m.Chicago O'Hare Intl

3 Mar

ORD10:35 a.m.Chicago O'Hare Intl

12h 16m

1 stop

YQR10:51 p.m.Regina

C$ 302

United Airlines

17 Mar

YQR9:45 a.m.Regina

13h 07m

1 stop

ORD11:52 p.m.Chicago O'Hare Intl

21 Mar

ORD10:37 a.m.Chicago O'Hare Intl

12h 42m

2 stops

YQR10:19 p.m.Regina

C$ 591

United Airlines

21 Mar

YQR5:00 a.m.Regina

7h 01m

1 stop

ORD1:01 p.m.Chicago O'Hare Intl

21 Mar

ORD3:55 p.m.Chicago O'Hare Intl

7h 24m

1 stop

YQR10:19 p.m.Regina

C$ 668

Fly from

Fly to

Route

Depart

Return

Price

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 23/2

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

1 stop7h 25m

Chicago O'Hare Intl

Mon 2/3

2:20 p.m.-10:32 a.m.

2 stops20h 12m

C$ 274

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 23/2

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

1 stop7h 25m

Chicago O'Hare Intl

Mon 2/3

2:20 p.m.-11:41 a.m.

1 stop21h 21m

C$ 281

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 24/2

10:45 a.m.-9:29 p.m.

1 stop10h 44m

Chicago O'Hare Intl

Tue 3/3

10:35 a.m.-10:51 p.m.

1 stop12h 16m

C$ 302

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 26/5

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

1 stop8h 48m

Chicago O'Hare Intl

Sat 30/5

5:30 p.m.-11:02 p.m.

1 stop6h 32m

C$ 334

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 26/5

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

2 stops22h 13m

Chicago O'Hare Intl

Sat 30/5

5:30 p.m.-11:02 p.m.

1 stop6h 32m

C$ 378

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 26/5

6:00 a.m.-8:24 p.m.

2 stops13h 24m

Chicago O'Hare Intl

Sat 30/5

8:55 a.m.-4:30 p.m.

2 stops8h 35m

C$ 405

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 24/2

11:35 a.m.-11:56 p.m.

2 stops12h 21m

Chicago O'Hare Intl

Tue 3/3

6:30 a.m.-6:31 p.m.

2 stops12h 01m

C$ 412

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 2/3

5:00 a.m.-7:45 p.m.

1 stop14h 45m

Chicago O'Hare Intl

Tue 3/3

8:40 p.m.-10:39 a.m.

1 stop13h 59m

C$ 428

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 2/3

5:00 a.m.-7:45 p.m.

1 stop14h 45m

Chicago O'Hare Intl

Tue 3/3

8:40 p.m.-10:39 a.m.

1 stop13h 59m

C$ 430

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 2/3

5:00 a.m.-7:45 p.m.

1 stop14h 45m

Chicago O'Hare Intl

Tue 3/3

12:50 p.m.-10:39 a.m.

2 stops21h 49m

C$ 474

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first

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

Prices

Airlines

Layovers

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 April is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 385.

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	6h 10m
Direct flights	None

The fastest flight from Regina to Chicago takes 6h 10m

There are no direct flights from Regina to Chicago. There are no popular flight routes from Regina to Chicago.

Search flight deals

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 6h 10m.
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 many operators does momondo search for flights from Regina Airport to Chicago?
There is 1 operator available for flights from Regina Airport to Chicago as of January 2026.
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?
momondo data reveals that the most frequently booked airline on the route from Regina to Chicago is WestJet, representing 67% of all bookings. The subsequent popular airline is Air Canada at 33%.

Best airlines flying from Regina to Chicago

Compare and see reviews for airlines that fly from Regina to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom C$ 498	Free Cancellation	Rating 7.1 10,616 reviews		Search Air Canada flights

Munster

Hammond

Merrillville

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.