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

Air Canada and Delta 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 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 September 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$ 256 Cheap Flights from Regina to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

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.

11:40 a.m. - 4:40 p.m.YQR Regina-ORD Chicago O'Hare Intl

28h 00m1 stop Calgary

5:30 p.m. - 11:20 p.m.ORD Chicago O'Hare Intl-YQR Regina

6h 50m1 stop Calgary

C$ 461WestJet

Wed, 14 Oct - Fri, 16 Oct

4:00 a.m. - 1:13 p.m.YQR Regina-ORD Chicago O'Hare Intl

8h 13m1 stop Toronto Pearson Intl

4:30 p.m. - 11:27 p.m.ORD Chicago O'Hare Intl-YQR Regina

6h 57m1 stop Toronto Pearson Intl

C$ 467Air Canada

Sat, 31 Oct - Sat, 7 Nov

11:50 a.m. - 4:40 p.m.YQR Regina-ORD Chicago O'Hare Intl

27h 50m2 stops Edmonton Calgary

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

8h 40m1 stop Calgary

C$ 467WestJet

Wed, 14 Oct - Fri, 16 Oct

5:00 a.m. - 3:38 p.m.YQR Regina-ORD Chicago O'Hare Intl

10h 38m1 stop Toronto Pearson Intl

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

14h 03m1 stop Toronto Pearson Intl

C$ 485Air Canada

Fri, 20 Nov - Sat, 28 Nov

5:00 a.m. - 1:13 p.m.YQR Regina-ORD Chicago O'Hare Intl

8h 13m1 stop Toronto Pearson Intl

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

14h 03m1 stop Toronto Pearson Intl

C$ 496Air Canada

Fri, 20 Nov - Sat, 28 Nov

5:00 a.m. - 1:13 p.m.YQR Regina-ORD Chicago O'Hare Intl

8h 13m1 stop Toronto Pearson Intl

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

14h 03m1 stop Toronto Pearson Intl

C$ 496Air Canada

Sat, 21 Nov - Sat, 28 Nov

5:00 a.m. - 1:13 p.m.YQR Regina-ORD Chicago O'Hare Intl

8h 13m1 stop Toronto Pearson Intl

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

14h 03m1 stop Toronto Pearson Intl

C$ 501Air Canada

Sat, 21 Nov - Sat, 28 Nov

6:00 a.m. - 5:40 p.m.YQR Regina-ORD Chicago O'Hare Intl

10h 40m1 stop Toronto Pearson Intl

12:20 p.m. - 1:20 a.m.ORD Chicago O'Hare Intl-YQR Regina

13h 00m1 stop Toronto Island

C$ 509Multiple Airlines

Fri, 30 Oct - Tue, 3 Nov

10:45 a.m. - 9:31 p.m.YQR Regina-ORD Chicago O'Hare Intl

10h 46m1 stop Denver Intl

2:37 p.m. - 10:41 p.m.ORD Chicago O'Hare Intl-YQR Regina

8h 04m1 stop Denver Intl

C$ 519United Airlines

Thu, 4 Feb - Mon, 8 Feb

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

6h 43m1 stop Toronto Pearson Intl

9:25 p.m. - 9:40 p.m.ORD Chicago O'Hare Intl-YQR Regina

25h 15m2 stops Minneapolis St Paul Denver Intl

C$ 699United Airlines

Sat, 24 Oct - Mon, 26 Oct

Cheap last-minute 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$ 589United Airlines

Tue, 22 Sep - Wed, 23 Sep

5:45 a.m. - 2:05 p.m.YQR Regina-ORD Chicago O'Hare Intl

7h 20m1 stop Toronto Pearson Intl

4:26 p.m. - 9:30 p.m.ORD Chicago O'Hare Intl-YQR Regina

6h 04m1 stop Denver Intl

C$ 1,278Air Canada

Tue, 22 Sep - Wed, 23 Sep

5:45 a.m. - 6:37 p.m.YQR Regina-ORD Chicago O'Hare Intl

11h 52m2 stops Toronto Pearson Intl Washington, D.C. Dulles Intl

10:55 a.m. - 9:30 p.m.ORD Chicago O'Hare Intl-YQR Regina

11h 35m1 stop Denver Intl

C$ 1,286Air Canada

Tue, 22 Sep - Wed, 23 Sep

5:45 a.m. - 2:55 p.m.YQR Regina-ORD Chicago O'Hare Intl

8h 10m1 stop Toronto Pearson Intl

12:59 p.m. - 7:05 p.m.ORD Chicago O'Hare Intl-YQR Regina

7h 06m1 stop Toronto Pearson Intl

C$ 1,442Air Canada

Tue, 22 Sep - Wed, 23 Sep

5:45 a.m. - 6:37 p.m.YQR Regina-ORD Chicago O'Hare Intl

11h 52m2 stops Toronto Pearson Intl Washington, D.C. Dulles Intl

7:09 a.m. - 1:25 p.m.ORD Chicago O'Hare Intl-YQR Regina

7h 16m1 stop Toronto Pearson Intl

C$ 1,450Air Canada

Tue, 22 Sep - Wed, 23 Sep

1:25 p.m. - 9:33 p.m.YQR Regina-ORD Chicago O'Hare Intl

7h 08m2 stops Winnipeg Minneapolis St Paul

8:25 a.m. - 5:20 p.m.ORD Chicago O'Hare Intl-YQR Regina

9h 55m1 stop Minneapolis St Paul

C$ 1,472WestJet

Tue, 22 Sep - Wed, 23 Sep

9:45 a.m. - 10:46 p.m.YQR Regina-ORD Chicago O'Hare Intl

12h 01m1 stop Denver Intl

7:09 a.m. - 1:25 p.m.ORD Chicago O'Hare Intl-YQR Regina

7h 16m1 stop Toronto Pearson Intl

C$ 1,478Air Canada

Tue, 22 Sep - Wed, 23 Sep

9:45 a.m. - 10:46 p.m.YQR Regina-ORD Chicago O'Hare Intl

12h 01m1 stop Denver Intl

7:09 a.m. - 1:25 p.m.ORD Chicago O'Hare Intl-YQR Regina

7h 16m1 stop Toronto Pearson Intl

C$ 1,479Air Canada

Tue, 22 Sep - Wed, 23 Sep

5:45 a.m. - 6:37 p.m.YQR Regina-ORD Chicago O'Hare Intl

11h 52m2 stops Toronto Pearson Intl Washington, D.C. Dulles Intl

10:55 a.m. - 9:30 p.m.ORD Chicago O'Hare Intl-YQR Regina

11h 35m1 stop Denver Intl

C$ 1,485Air Canada

Tue, 22 Sep - Wed, 23 Sep

5:45 a.m. - 6:37 p.m.YQR Regina-ORD Chicago O'Hare Intl

11h 52m2 stops Toronto Pearson Intl Washington, D.C. Dulles Intl

10:55 a.m. - 9:30 p.m.ORD Chicago O'Hare Intl-YQR Regina

11h 35m1 stop Denver Intl

C$ 1,486Air Canada

Tue, 22 Sep - Wed, 23 Sep

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United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets

United Airlines

4 Feb

YQR10:45 a.m.Regina

10h 46m

1 stop

ORD9:31 p.m.Chicago O'Hare Intl

8 Feb

ORD2:37 p.m.Chicago O'Hare Intl

8h 04m

1 stop

YQR10:41 p.m.Regina

C$ 519

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$ 589

United Airlines

24 Oct

YQR5:40 a.m.Regina

6h 43m

1 stop

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

26 Oct

ORD9:25 p.m.Chicago O'Hare Intl

25h 15m

2 stops

YQR9:40 p.m.Regina

C$ 699

Delta flights from Regina to Chicago

Our best Delta deals on Regina to Chicago flight tickets

Delta

28 Sep

YQR8:35 a.m.Regina

11h 58m

2 stops

ORD9:33 p.m.Chicago O'Hare Intl

1 Oct

ORD8:25 a.m.Chicago O'Hare Intl

9h 55m

1 stop

YQR5:20 p.m.Regina

C$ 548

Delta

30 Oct

YQR11:50 a.m.Regina

8h 37m

1 stop

ORD9:27 p.m.Chicago O'Hare Intl

3 Nov

ORD5:27 a.m.Chicago O'Hare Intl

13h 13m

2 stops

YQR6:40 p.m.Regina

C$ 562

Delta

21 Nov

YQR5:35 a.m.Regina

11h 06m

2 stops

ORD4:41 p.m.Chicago O'Hare Intl

28 Nov

ORD9:59 a.m.Chicago O'Hare Intl

8h 41m

1 stop

YQR6:40 p.m.Regina

C$ 563

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Wed 14/10

11:40 a.m.-4:40 p.m.

1 stop28h 00m

Chicago O'Hare Intl

Fri 16/10

5:30 p.m.-11:20 p.m.

1 stop6h 50m

C$ 461

Quickest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 31/10

4:00 a.m.-1:13 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sat 7/11

4:30 p.m.-11:27 p.m.

1 stop6h 57m

C$ 467

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Wed 14/10

11:50 a.m.-4:40 p.m.

2 stops27h 50m

Chicago O'Hare Intl

Fri 16/10

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

1 stop8h 40m

C$ 467

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 20/11

5:00 a.m.-3:38 p.m.

1 stop10h 38m

Chicago O'Hare Intl

Sat 28/11

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

1 stop14h 03m

C$ 485

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 20/11

5:00 a.m.-1:13 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sat 28/11

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

1 stop14h 03m

C$ 496

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 21/11

5:00 a.m.-1:13 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sat 28/11

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

1 stop14h 03m

C$ 496

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 21/11

5:00 a.m.-1:13 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sat 28/11

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

1 stop14h 03m

C$ 501

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 30/10

6:00 a.m.-5:40 p.m.

1 stop10h 40m

Chicago O'Hare Intl

Tue 3/11

12:20 p.m.-1:20 a.m.

1 stop13h 00m

C$ 509

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 4/2

10:45 a.m.-9:31 p.m.

1 stop10h 46m

Chicago O'Hare Intl

Mon 8/2

2:37 p.m.-10:41 p.m.

1 stop8h 04m

C$ 519

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 24/10

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

1 stop6h 43m

Chicago O'Hare Intl

Mon 26/10

9:25 p.m.-9:40 p.m.

2 stops25h 15m

C$ 699

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 June is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 608.

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$ 256
Fastest flight time	6h 43m
Direct flights	None

The best one-way flight to Chicago from Regina in the past 72 hours is C$ 256. The best round-trip flight deal from Regina to Chicago found on momondo in the last 72 hours is C$ 461.

The fastest flight from Regina to Chicago takes 6h 43m

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

Search flight deals

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 43m.
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 September 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 37% of all bookings. The subsequent popular airlines are Air Canada at 32% and United Airlines at 32%.

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
United Airlines	PriceFrom C$ 431	Free Cancellation	Rating 7.4 10,227 reviews		Search United Airlines flights

Merrillville

Benton Harbor

Hammond

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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Fly into one of these airports located in Chicago

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Chicago O'Hare Intl Airport

Cheap flights from Regina to Chicago from C$ 256

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.

Find the cheapest flights from Regina to Chicago

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Big names, great deals

Big names, great deals

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Filter for what you want

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United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets

Delta flights from Regina to Chicago

Our best Delta deals on Regina to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Regina to Chicago that are best for you.

See travel insights to Chicago from

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

Best airlines flying from Regina to Chicago

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

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

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

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.

Popular Cities in the United States

Popular flights according to clicks in the last 7 days on momondo

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According to popular flight searches on momondo this year

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