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

Air Canada, United Airlines, and WestJet are the most popular carriers 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 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$ 245 Cheap Flights from Regina to Chicago in 2026

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.

9:45 a.m. - 6:32 p.m.YQR Regina-ORD Chicago O'Hare Intl

7h 47m1 stop Denver Intl

5:55 a.m. - 9:30 p.m.ORD Chicago O'Hare Intl-YQR Regina

16h 35m1 stop Denver Intl

C$ 420United Airlines

Tue, 22 Sep - Wed, 23 Sep

9:45 a.m. - 6:32 p.m.YQR Regina-ORD Chicago O'Hare Intl

7h 47m1 stop Denver Intl

5:55 a.m. - 9:30 p.m.ORD Chicago O'Hare Intl-YQR Regina

16h 35m1 stop Denver Intl

C$ 430United Airlines

Tue, 22 Sep - Wed, 23 Sep

10:45 a.m. - 11:59 p.m.YQR Regina-ORD Chicago O'Hare Intl

13h 14m1 stop Denver Intl

8:40 p.m. - 10:43 a.m.ORD Chicago O'Hare Intl-YQR Regina

14h 03m1 stop Toronto Pearson Intl

C$ 432Multiple Airlines

Sat, 21 Nov - Sat, 28 Nov

9:45 a.m. - 6:32 p.m.YQR Regina-ORD Chicago O'Hare Intl

7h 47m1 stop Denver Intl

5:55 a.m. - 9:30 p.m.ORD Chicago O'Hare Intl-YQR Regina

16h 35m1 stop Denver Intl

C$ 435United Airlines

Tue, 22 Sep - Wed, 23 Sep

10:45 a.m. - 11:57 p.m.YQR Regina-ORD Chicago O'Hare Intl

12h 12m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

9:59 a.m. - 6:40 p.m.ORD Chicago O'Hare Intl-YQR Regina

9h 41m1 stop Minneapolis St Paul

C$ 457Delta

Sat, 24 Oct - Sat, 31 Oct

5:40 a.m. - 1:23 p.m.YQR Regina-ORD Chicago O'Hare Intl

6h 43m1 stop Toronto Pearson Intl

8:40 p.m. - 9:00 a.m.ORD Chicago O'Hare Intl-YQR Regina

13h 20m1 stop Toronto Pearson Intl

C$ 489Air Canada

Sat, 3 Oct - Mon, 5 Oct

10:45 a.m. - 9:27 p.m.YQR Regina-ORD Chicago O'Hare Intl

9h 42m1 stop Minneapolis St Paul

7:00 a.m. - 5:20 p.m.ORD Chicago O'Hare Intl-YQR Regina

11h 20m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul

C$ 497Delta

Tue, 6 Oct - Fri, 9 Oct

5:40 a.m. - 1:23 p.m.YQR Regina-ORD Chicago O'Hare Intl

6h 43m1 stop Toronto Pearson Intl

8:40 p.m. - 9:00 a.m.ORD Chicago O'Hare Intl-YQR Regina

13h 20m1 stop Toronto Pearson Intl

C$ 500Air Canada

Sun, 4 Oct - Tue, 6 Oct

5:45 a.m. - 1:23 p.m.YQR Regina-ORD Chicago O'Hare Intl

6h 38m1 stop Toronto Pearson Intl

9:55 a.m. - 7:05 p.m.ORD Chicago O'Hare Intl-YQR Regina

10h 10m1 stop Toronto Pearson Intl

C$ 508Air Canada

Tue, 22 Sep - Wed, 23 Sep

8:20 p.m. - 4:40 p.m.YQR Regina-ORD Chicago O'Hare Intl

19h 20m2 stops Edmonton Calgary

5:30 p.m. - 1:10 a.m.ORD Chicago O'Hare Intl-YQR Regina

8h 40m1 stop Calgary

C$ 517WestJet

Sun, 4 Oct - Tue, 6 Oct

Cheap last-minute flights

Enter your travel dates to find the best prices.

10:45 a.m. - 8:30 p.m.YQR Regina-ORD Chicago O'Hare Intl

8h 45m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County

8:55 a.m. - 12:35 a.m.ORD Chicago O'Hare Intl-YQR Regina

16h 40m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

C$ 593Delta

Wed, 9 Sep - Fri, 11 Sep

10:45 a.m. - 9:33 p.m.YQR Regina-ORD Chicago O'Hare Intl

9h 48m1 stop Minneapolis St Paul

6:10 a.m. - 5:20 p.m.ORD Chicago O'Hare Intl-YQR Regina

12h 10m1 stop Minneapolis St Paul

C$ 808Delta

Wed, 9 Sep - Fri, 11 Sep

10:45 a.m. - 11:59 p.m.YQR Regina-ORD Chicago O'Hare Intl

12h 14m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

5:30 p.m. - 1:10 a.m.ORD Chicago O'Hare Intl-YQR Regina

8h 40m1 stop Calgary

C$ 847Multiple Airlines

Tue, 8 Sep - Fri, 11 Sep

10:45 a.m. - 9:33 p.m.YQR Regina-ORD Chicago O'Hare Intl

9h 48m1 stop Minneapolis St Paul

12:29 p.m. - 1:10 a.m.ORD Chicago O'Hare Intl-YQR Regina

13h 41m2 stops Minneapolis St Paul Calgary

C$ 852Delta

Tue, 8 Sep - Fri, 11 Sep

10:45 a.m. - 9:33 p.m.YQR Regina-ORD Chicago O'Hare Intl

9h 48m1 stop Minneapolis St Paul

5:30 p.m. - 1:10 a.m.ORD Chicago O'Hare Intl-YQR Regina

8h 40m1 stop Calgary

C$ 858Multiple Airlines

Tue, 8 Sep - Fri, 11 Sep

10:45 a.m. - 11:59 p.m.YQR Regina-ORD Chicago O'Hare Intl

12h 14m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

8:55 a.m. - 12:35 a.m.ORD Chicago O'Hare Intl-YQR Regina

16h 40m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

C$ 915Delta

Tue, 8 Sep - Fri, 11 Sep

10:45 a.m. - 11:59 p.m.YQR Regina-ORD Chicago O'Hare Intl

12h 14m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

8:55 a.m. - 12:35 a.m.ORD Chicago O'Hare Intl-YQR Regina

16h 40m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

C$ 919Delta

Tue, 8 Sep - Fri, 11 Sep

4:15 p.m. - 11:00 a.m.YQR Regina-MDW Chicago Midway

17h 45m2 stops Calgary Toronto Pearson Intl

3:20 p.m. - 12:35 a.m.MDW Chicago Midway-YQR Regina

10h 15m1 stop Toronto Island

C$ 1,445Multiple Airlines

Mon, 7 Sep - Tue, 8 Sep

6:00 a.m. - 11:00 a.m.YQR Regina-MDW Chicago Midway

28h 00m1 stop Toronto Pearson Intl

3:20 p.m. - 12:35 a.m.MDW Chicago Midway-YQR Regina

10h 15m1 stop Toronto Island

C$ 1,477Multiple Airlines

Mon, 7 Sep - Tue, 8 Sep

2:15 p.m. - 8:00 a.m.YQR Regina-ORD Chicago O'Hare Intl

16h 45m1 stop Toronto Pearson Intl

5:53 p.m. - 9:00 a.m.ORD Chicago O'Hare Intl-YQR Regina

16h 07m1 stop Toronto Pearson Intl

C$ 1,623Air Canada

Mon, 7 Sep - Tue, 8 Sep

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Air Canada flights from Regina to Chicago

Our best Air Canada deals on Regina to Chicago flight tickets

Air Canada

3 Oct

YQR5:40 a.m.Regina

6h 43m

1 stop

ORD1:23 p.m.Chicago O'Hare Intl

5 Oct

ORD8:40 p.m.Chicago O'Hare Intl

13h 20m

1 stop

YQR9:00 a.m.Regina

C$ 489

Air Canada

4 Oct

YQR5:40 a.m.Regina

6h 43m

1 stop

ORD1:23 p.m.Chicago O'Hare Intl

6 Oct

ORD8:40 p.m.Chicago O'Hare Intl

13h 20m

1 stop

YQR9:00 a.m.Regina

C$ 500

Air Canada

22 Sep

YQR5:45 a.m.Regina

6h 38m

1 stop

ORD1:23 p.m.Chicago O'Hare Intl

23 Sep

ORD9:55 a.m.Chicago O'Hare Intl

10h 10m

1 stop

YQR7:05 p.m.Regina

C$ 508

United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets

United Airlines

22 Sep

YQR9:45 a.m.Regina

7h 47m

1 stop

ORD6:32 p.m.Chicago O'Hare Intl

23 Sep

ORD5:55 a.m.Chicago O'Hare Intl

16h 35m

1 stop

YQR9:30 p.m.Regina

C$ 420

United Airlines

22 Sep

YQR9:45 a.m.Regina

7h 47m

1 stop

ORD6:32 p.m.Chicago O'Hare Intl

23 Sep

ORD5:55 a.m.Chicago O'Hare Intl

16h 35m

1 stop

YQR9:30 p.m.Regina

C$ 430

United Airlines

22 Sep

YQR9:45 a.m.Regina

7h 47m

1 stop

ORD6:32 p.m.Chicago O'Hare Intl

23 Sep

ORD5:55 a.m.Chicago O'Hare Intl

16h 35m

1 stop

YQR9:30 p.m.Regina

C$ 435

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 22/9

9:45 a.m.-6:32 p.m.

1 stop7h 47m

Chicago O'Hare Intl

Wed 23/9

5:55 a.m.-9:30 p.m.

1 stop16h 35m

C$ 420

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 22/9

9:45 a.m.-6:32 p.m.

1 stop7h 47m

Chicago O'Hare Intl

Wed 23/9

5:55 a.m.-9:30 p.m.

1 stop16h 35m

C$ 430

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 21/11

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

1 stop13h 14m

Chicago O'Hare Intl

Sat 28/11

8:40 p.m.-10:43 a.m.

1 stop14h 03m

C$ 432

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 22/9

9:45 a.m.-6:32 p.m.

1 stop7h 47m

Chicago O'Hare Intl

Wed 23/9

5:55 a.m.-9:30 p.m.

1 stop16h 35m

C$ 435

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 24/10

10:45 a.m.-11:57 p.m.

2 stops12h 12m

Chicago O'Hare Intl

Sat 31/10

9:59 a.m.-6:40 p.m.

1 stop9h 41m

C$ 457

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 3/10

5:40 a.m.-1:23 p.m.

1 stop6h 43m

Chicago O'Hare Intl

Mon 5/10

8:40 p.m.-9:00 a.m.

1 stop13h 20m

C$ 489

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 6/10

10:45 a.m.-9:27 p.m.

1 stop9h 42m

Chicago O'Hare Intl

Fri 9/10

7:00 a.m.-5:20 p.m.

2 stops11h 20m

C$ 497

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sun 4/10

5:40 a.m.-1:23 p.m.

1 stop6h 43m

Chicago O'Hare Intl

Tue 6/10

8:40 p.m.-9:00 a.m.

1 stop13h 20m

C$ 500

Quickest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 22/9

5:45 a.m.-1:23 p.m.

1 stop6h 38m

Chicago O'Hare Intl

Wed 23/9

9:55 a.m.-7:05 p.m.

1 stop10h 10m

C$ 508

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sun 4/10

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

2 stops19h 20m

Chicago O'Hare Intl

Tue 6/10

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

1 stop8h 40m

C$ 517

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

Airlines

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$ 481.

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

Best price found	C$ 245
Fastest flight time	6h 14m
Direct flights	None

The best one-way flight to Chicago from Regina in the past 72 hours is C$ 245. The best round-trip flight deal from Regina to Chicago found on momondo in the last 72 hours is C$ 420.

The fastest flight from Regina to Chicago takes 6h 14m

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

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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 6h 14m.
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?
momondo data reveals that the most frequently booked airline on the route from Regina to Chicago is WestJet, representing 37% of all bookings. The subsequent popular airlines are Air Canada at 32% and United Airlines at 32%.

Merrillville

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Munster

Valparaiso

Portage

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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Cheap flights from Regina to Chicago from C$ 245

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 31/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names, great deals

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Air Canada flights from Regina to Chicago

Our best Air Canada deals on Regina to Chicago flight tickets

United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets

momondo Fare Finder

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How to get the cheapest flight ticket from Regina to Chicago

What is the cheapest month to fly to Chicago?

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

When to book flights from Regina to Chicago

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

Best price found

Fastest flight time

Direct flights

Frequently asked questions about flying from Regina to Chicago

Travelling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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