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$ 374.

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.

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$ 170 Cheap Flights from Regina to Chicago in 2025/26

1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Regina to Chicago

Round-trip

One-way

Last minute

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. - 9:08 p.m.

ORD

YQR

6h 48m1 stop

C$ 318WestJet

Fri, 23 Jan - Fri, 30 Jan

4:25 p.m. - 5:56 p.m.

YQR

ORD

25h 31m2 stops

2:20 p.m. - 9:08 p.m.

ORD

YQR

6h 48m1 stop

C$ 349Multiple Airlines

Wed, 28 Jan - Fri, 30 Jan

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

YQR

ORD

8h 01m1 stop

7:00 a.m. - 10:51 p.m.

ORD

YQR

15h 51m1 stop

C$ 392United Airlines

Wed, 28 Jan - Fri, 30 Jan

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

YQR

ORD

7h 25m1 stop

2:20 p.m. - 10:30 a.m.

ORD

YQR

44h 10m2 stops

C$ 405WestJet

Fri, 23 Jan - Fri, 30 Jan

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

YQR

ORD

7h 25m1 stop

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

ORD

YQR

44h 12m2 stops

C$ 445WestJet

Fri, 16 Jan - Fri, 23 Jan

10:45 a.m. - 11:34 a.m.

YQR

ORD

24h 49m2 stops

7:00 a.m. - 10:51 p.m.

ORD

YQR

15h 51m1 stop

C$ 479United Airlines

Sun, 25 Jan - Thu, 29 Jan

11:45 a.m. - 6:36 p.m.

YQR

MDW

6h 51m1 stop

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

MDW

YQR

8h 30m1 stop

C$ 488Delta

Fri, 23 Jan - Fri, 30 Jan

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

YQR

ORD

12h 14m2 stops

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

ORD

YQR

11h 30m2 stops

C$ 490Delta

Fri, 16 Jan - Fri, 23 Jan

11:45 a.m. - 6:36 p.m.

YQR

MDW

6h 51m1 stop

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

MDW

YQR

8h 30m1 stop

C$ 490Delta

Mon, 26 Jan - Fri, 30 Jan

5:00 a.m. - 6:51 p.m.

YQR

ORD

13h 51m2 stops

6:28 p.m. - 10:39 a.m.

ORD

YQR

16h 11m1 stop

C$ 529Air Canada

Wed, 28 Jan - Thu, 29 Jan

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets

WestJet

23 Jan

YQR6:10 a.m.Regina

7h 25m

1 stop

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

30 Jan

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

6h 48m

1 stop

YQR9:08 p.m.Regina

C$ 318

Find similar

WestJet

23 Jan

YQR6:10 a.m.Regina

7h 25m

1 stop

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

30 Jan

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

44h 10m

2 stops

YQR10:30 a.m.Regina

C$ 405

Find similar

WestJet

16 Jan

YQR6:10 a.m.Regina

7h 25m

1 stop

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

23 Jan

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

44h 12m

2 stops

YQR10:32 a.m.Regina

C$ 445

Find similar

United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets

United Airlines

28 Jan

YQR10:45 a.m.Regina

6h 19m

1 stop

ORD5:04 p.m.Chicago O'Hare Intl

29 Jan

ORD7:00 a.m.Chicago O'Hare Intl

15h 51m

1 stop

YQR10:51 p.m.Regina

C$ 392

Find similar

United Airlines

25 Jan

YQR10:45 a.m.Regina

24h 49m

2 stops

ORD11:34 a.m.Chicago O'Hare Intl

29 Jan

ORD7:00 a.m.Chicago O'Hare Intl

15h 51m

1 stop

YQR10:51 p.m.Regina

C$ 479

Find similar

United Airlines

25 Jan

YQR10:45 a.m.Regina

24h 49m

2 stops

ORD11:34 a.m.Chicago O'Hare Intl

29 Jan

ORD8:18 p.m.Chicago O'Hare Intl

26h 33m

2 stops

YQR10:51 p.m.Regina

C$ 608

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 23/1

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

1 stop7h 25m

Chicago O'Hare Intl

Fri 30/1

2:20 p.m.-9:08 p.m.

1 stop6h 48m

C$ 318

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 28/1

4:25 p.m.-5:56 p.m.

2 stops25h 31m

Chicago O'Hare Intl

Fri 30/1

2:20 p.m.-9:08 p.m.

1 stop6h 48m

C$ 349

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 28/1

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

1 stop8h 01m

Chicago O'Hare Intl

Fri 30/1

7:00 a.m.-10:51 p.m.

1 stop15h 51m

C$ 392

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 23/1

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

1 stop7h 25m

Chicago O'Hare Intl

Fri 30/1

2:20 p.m.-10:30 a.m.

2 stops44h 10m

C$ 405

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 16/1

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

1 stop7h 25m

Chicago O'Hare Intl

Fri 23/1

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

2 stops44h 12m

C$ 445

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 25/1

10:45 a.m.-11:34 a.m.

2 stops24h 49m

Chicago O'Hare Intl

Thu 29/1

7:00 a.m.-10:51 p.m.

1 stop15h 51m

C$ 479

ReginaChicago

YQR - MDW

YQRMDW

Regina

Fri 23/1

11:45 a.m.-6:36 p.m.

1 stop6h 51m

Chicago Midway

Fri 30/1

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

1 stop8h 30m

C$ 488

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 16/1

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

2 stops12h 14m

Chicago O'Hare Intl

Fri 23/1

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

2 stops11h 30m

C$ 490

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 26/1

11:45 a.m.-6:36 p.m.

1 stop6h 51m

Chicago Midway

Fri 30/1

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

1 stop8h 30m

C$ 490

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 28/1

5:00 a.m.-6:51 p.m.

2 stops13h 51m

Chicago O'Hare Intl

Thu 29/1

6:28 p.m.-10:39 a.m.

1 stop16h 11m

C$ 529

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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

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$ 374.

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$ 409. 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$ 960. 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$ 467. 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$ 706 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 5h 39m.
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 72% of all bookings. The subsequent popular airline is Air Canada at 28%.

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$ 410	Free Cancellation	Rating 7.1 10,500 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.