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.

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

Flights via Calgary (YYC) offer the lowest average round-trip price of C$ 376.

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.

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.

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

WestJet is the most popular carrier operating from Regina to Chicago

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 November 2025.

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$ 206 Cheap Flights from Regina to Chicago in 2025/26

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

Prices are currently typical for flights on this route. Typical prices usually range from C$ 402 to C$ 839. The lowest price recently found on this route was C$ 437.

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

8h 48m1 stop

5:30 p.m. - 10:57 a.m.ORD-YQR

18h 27m1 stop

C$ 437WestJet

Find Deal

Sun, 3 May - Mon, 4 May

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

7h 25m1 stop

10:38 p.m. - 4:08 p.m.ORD-YQR

41h 30m2 stops

C$ 440Multiple Airlines

Find Deal

Mon, 19 Jan - Fri, 13 Feb

11:40 a.m. - 1:23 p.m.YQR-ORD

49h 43m2 stops

7:38 p.m. - 6:20 p.m.ORD-YQR

22h 42m1 stop

C$ 447Multiple Airlines

Find Deal

Mon, 1 Dec - Mon, 22 Dec

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

8h 48m1 stop

5:30 p.m. - 1:07 a.m.ORD-YQR

8h 37m1 stop

C$ 483Delta

Find Deal

Sun, 3 May - Mon, 4 May

11:40 a.m. - 7:22 p.m.YQR-ORD

7h 42m1 stop

7:38 p.m. - 6:20 p.m.ORD-YQR

22h 42m1 stop

C$ 485Multiple Airlines

Find Deal

Mon, 1 Dec - Mon, 22 Dec

11:40 a.m. - 9:40 p.m.YQR-ORD

10h 00m1 stop

8:50 a.m. - 6:20 p.m.ORD-YQR

9h 30m1 stop

C$ 490Delta

Find Deal

Wed, 10 Dec - Tue, 16 Dec

2:25 p.m. - 9:54 a.m.YQR-ORD

18h 29m2 stops

3:40 p.m. - 9:33 a.m.ORD-YQR

18h 53m2 stops

C$ 497Air Canada

Find Deal

Sun, 3 May - Mon, 4 May

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

8h 48m1 stop

5:30 p.m. - 9:30 a.m.ORD-YQR

17h 00m2 stops

C$ 537WestJet

Find Deal

Sun, 3 May - Mon, 4 May

11:40 a.m. - 6:40 p.m.YQR-ORD

7h 00m1 stop

10:00 a.m. - 6:20 p.m.ORD-YQR

8h 20m1 stop

C$ 551Multiple Airlines

Find Deal

Wed, 26 Nov - Sat, 29 Nov

6:10 a.m. - 9:48 p.m.YQR-ORD

15h 38m2 stops

7:20 a.m. - 6:45 p.m.ORD-YQR

35h 25m3 stops

C$ 576Multiple Airlines

Find Deal

Wed, 10 Dec - Tue, 16 Dec

United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets

United Airlines

3 May

YQR9:45 a.m.Regina

11h 40m

1 stop

ORD10:25 p.m.Chicago O'Hare Intl

4 May

ORD2:18 p.m.Chicago O'Hare Intl

8h 18m

1 stop

YQR9:36 p.m.Regina

C$ 779

Find similar

United Airlines

1 Dec

YQR10:45 a.m.Regina

13h 13m

1 stop

ORD11:58 p.m.Chicago O'Hare Intl

20 Dec

ORD1:48 p.m.Chicago O'Hare Intl

9h 03m

1 stop

YQR10:51 p.m.Regina

C$ 1,032

Find similar

United Airlines

1 Dec

YQR10:45 a.m.Regina

22h 56m

2 stops

ORD9:41 a.m.Chicago O'Hare Intl

20 Dec

ORD1:48 p.m.Chicago O'Hare Intl

9h 03m

1 stop

YQR10:51 p.m.Regina

C$ 1,076

Find similar

Air Canada flights from Regina to Chicago

Our best Air Canada deals on Regina to Chicago flight tickets

Air Canada

3 May

YQR2:25 p.m.Regina

18h 29m

2 stops

ORD9:54 a.m.Chicago O'Hare Intl

4 May

ORD3:40 p.m.Chicago O'Hare Intl

18h 53m

2 stops

YQR9:33 a.m.Regina

C$ 497

Find similar

Air Canada

3 May

YQR2:25 p.m.Regina

18h 29m

2 stops

ORD9:54 a.m.Chicago O'Hare Intl

4 May

ORD3:40 p.m.Chicago O'Hare Intl

18h 53m

2 stops

YQR9:33 a.m.Regina

C$ 843

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 3/5

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

1 stop8h 48m

Chicago O'Hare Intl

Mon 4/5

5:30 p.m.-10:57 a.m.

1 stop18h 27m

C$ 437

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 19/1

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

1 stop7h 25m

Chicago O'Hare Intl

Fri 13/2

10:38 p.m.-4:08 p.m.

2 stops41h 30m

C$ 440

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 1/12

11:40 a.m.-1:23 p.m.

2 stops49h 43m

Chicago O'Hare Intl

Mon 22/12

7:38 p.m.-6:20 p.m.

1 stop22h 42m

C$ 447

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 3/5

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

1 stop8h 48m

Chicago O'Hare Intl

Mon 4/5

5:30 p.m.-1:07 a.m.

1 stop8h 37m

C$ 483

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 1/12

11:40 a.m.-7:22 p.m.

1 stop7h 42m

Chicago O'Hare Intl

Mon 22/12

7:38 p.m.-6:20 p.m.

1 stop22h 42m

C$ 485

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 10/12

11:40 a.m.-9:40 p.m.

1 stop10h 00m

Chicago O'Hare Intl

Tue 16/12

8:50 a.m.-6:20 p.m.

1 stop9h 30m

C$ 490

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 3/5

2:25 p.m.-9:54 a.m.

2 stops18h 29m

Chicago O'Hare Intl

Mon 4/5

3:40 p.m.-9:33 a.m.

2 stops18h 53m

C$ 497

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 3/5

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

1 stop8h 48m

Chicago O'Hare Intl

Mon 4/5

5:30 p.m.-9:30 a.m.

2 stops17h 00m

C$ 537

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 26/11

11:40 a.m.-6:40 p.m.

1 stop7h 00m

Chicago O'Hare Intl

Sat 29/11

10:00 a.m.-6:20 p.m.

1 stop8h 20m

C$ 551

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 10/12

6:10 a.m.-9:48 p.m.

2 stops15h 38m

Chicago O'Hare Intl

Tue 16/12

7:20 a.m.-6:45 p.m.

3 stops35h 25m

C$ 576

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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 September is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 375.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as C$ 411. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 964. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the afternoon is the cheapest time of day to fly from Regina to Chicago when you can find flight prices for as low as C$ 469. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 709 per ticket.

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

Direct flights	None

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

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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 02m.
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 November 2025.
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 69% of all bookings. The subsequent popular airline is Air Canada at 31%.

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$ 412	Free Cancellation	Rating 7.1 10,444 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.