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.

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

United Airlines and WestJet are the most popular carriers operating from Regina to Chicago

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

Flights via Calgary (YYC) offer the lowest average round-trip price of C$ 370.

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 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.

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 December 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$ 197 Cheap Flights from Regina to Chicago in 2025/26

1 adult

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

4:25 p.m. - 1:35 p.m.

YQR

ORD

21h 10m1 stop

2:20 p.m. - 9:06 p.m.

ORD

YQR

6h 46m1 stop

C$ 302WestJet

Thu, 5 Feb - Mon, 9 Feb

10:45 a.m. - 11:59 p.m.

YQR

ORD

13h 14m1 stop

7:10 a.m. - 10:51 p.m.

ORD

YQR

15h 41m1 stop

C$ 306United Airlines

Sat, 10 Jan - Wed, 4 Mar

7:05 a.m. - 1:35 p.m.

YQR

ORD

30h 30m2 stops

2:20 p.m. - 9:06 p.m.

ORD

YQR

6h 46m1 stop

C$ 405WestJet

Thu, 5 Feb - Mon, 9 Feb

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

YQR

ORD

19h 25m2 stops

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

ORD

YQR

44h 12m2 stops

C$ 413WestJet

Thu, 5 Feb - Mon, 9 Feb

10:45 a.m. - 6:46 p.m.

YQR

ORD

8h 01m1 stop

7:25 a.m. - 10:51 p.m.

ORD

YQR

15h 26m2 stops

C$ 478United Airlines

Sat, 10 Jan - Wed, 4 Mar

10:45 a.m. - 6:46 p.m.

YQR

ORD

8h 01m1 stop

1:55 p.m. - 10:51 p.m.

ORD

YQR

8h 56m1 stop

C$ 497United Airlines

Thu, 5 Feb - Mon, 9 Feb

11:45 a.m. - 12:48 p.m.

YQR

MDW

25h 03m2 stops

9:50 a.m. - 6:20 p.m.

MDW

YQR

8h 30m1 stop

C$ 546Delta

Sun, 11 Jan - Thu, 15 Jan

7:00 a.m. - 2:17 p.m.

YQR

ORD

31h 17m3 stops

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

ORD

YQR

20h 12m2 stops

C$ 561Multiple Airlines

Thu, 5 Feb - Mon, 9 Feb

5:40 a.m. - 8:17 p.m.

YQR

ORD

14h 37m2 stops

1:55 p.m. - 10:51 p.m.

ORD

YQR

8h 56m1 stop

C$ 579United Airlines

Mon, 12 Jan - Thu, 15 Jan

11:45 a.m. - 8:40 a.m.

YQR

ORD

20h 55m1 stop

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

ORD

YQR

9h 30m1 stop

C$ 617Delta

Mon, 12 Jan - Thu, 15 Jan

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets

WestJet

5 Feb

YQR4:25 p.m.Regina

21h 10m

1 stop

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

9 Feb

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

6h 46m

1 stop

YQR9:06 p.m.Regina

C$ 302

Find similar

WestJet

5 Feb

YQR7:05 a.m.Regina

30h 30m

2 stops

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

9 Feb

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

6h 46m

1 stop

YQR9:06 p.m.Regina

C$ 405

Find similar

WestJet

5 Feb

YQR6:10 p.m.Regina

19h 25m

2 stops

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

9 Feb

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

44h 12m

2 stops

YQR10:32 a.m.Regina

C$ 413

Find similar

United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets

United Airlines

10 Jan

YQR10:45 a.m.Regina

13h 14m

1 stop

ORD11:59 p.m.Chicago O'Hare Intl

4 Mar

ORD7:10 a.m.Chicago O'Hare Intl

15h 41m

1 stop

YQR10:51 p.m.Regina

C$ 306

Find similar

United Airlines

10 Jan

YQR10:45 a.m.Regina

8h 01m

1 stop

ORD6:46 p.m.Chicago O'Hare Intl

4 Mar

ORD7:25 a.m.Chicago O'Hare Intl

15h 26m

2 stops

YQR10:51 p.m.Regina

C$ 478

Find similar

United Airlines

5 Feb

YQR10:45 a.m.Regina

8h 01m

1 stop

ORD6:46 p.m.Chicago O'Hare Intl

9 Feb

ORD1:55 p.m.Chicago O'Hare Intl

8h 56m

1 stop

YQR10:51 p.m.Regina

C$ 497

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/2

4:25 p.m.-1:35 p.m.

1 stop21h 10m

Chicago O'Hare Intl

Mon 9/2

2:20 p.m.-9:06 p.m.

1 stop6h 46m

C$ 302

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 10/1

10:45 a.m.-11:59 p.m.

1 stop13h 14m

Chicago O'Hare Intl

Wed 4/3

7:10 a.m.-10:51 p.m.

1 stop15h 41m

C$ 306

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/2

7:05 a.m.-1:35 p.m.

2 stops30h 30m

Chicago O'Hare Intl

Mon 9/2

2:20 p.m.-9:06 p.m.

1 stop6h 46m

C$ 405

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/2

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

2 stops19h 25m

Chicago O'Hare Intl

Mon 9/2

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

2 stops44h 12m

C$ 413

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 10/1

10:45 a.m.-6:46 p.m.

1 stop8h 01m

Chicago O'Hare Intl

Wed 4/3

7:25 a.m.-10:51 p.m.

2 stops15h 26m

C$ 478

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/2

10:45 a.m.-6:46 p.m.

1 stop8h 01m

Chicago O'Hare Intl

Mon 9/2

1:55 p.m.-10:51 p.m.

1 stop8h 56m

C$ 497

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sun 11/1

11:45 a.m.-12:48 p.m.

2 stops25h 03m

Chicago Midway

Thu 15/1

9:50 a.m.-6:20 p.m.

1 stop8h 30m

C$ 546

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/2

7:00 a.m.-2:17 p.m.

3 stops31h 17m

Chicago O'Hare Intl

Mon 9/2

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

2 stops20h 12m

C$ 561

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 12/1

5:40 a.m.-8:17 p.m.

2 stops14h 37m

Chicago O'Hare Intl

Thu 15/1

1:55 p.m.-10:51 p.m.

1 stop8h 56m

C$ 579

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 12/1

11:45 a.m.-8:40 a.m.

1 stop20h 55m

Chicago O'Hare Intl

Thu 15/1

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

1 stop9h 30m

C$ 617

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 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$ 369.

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$ 404. 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$ 948. 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$ 461. 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$ 697 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

Fastest flight time	6h 38m
Direct flights	None

The fastest flight from Regina to Chicago takes 6h 38m

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 38m.
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 December 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 70% of all bookings. The subsequent popular airline is Air Canada at 30%.

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$ 405	Free Cancellation	Rating 7.1 10,534 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.