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Cheap flights from Regina to Chicago from C$ 356

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Regina to Chicago departing on 21/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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Find the cheapest flights from Regina to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:40 a.m. - 9:50 a.m.YQR-ORD
22h 10m1 stop
Multiple Airlines Logo
12:26 p.m. - 6:20 p.m.ORD-YQR
5h 54m1 stop
C$ 356Multiple Airlines
Find Deal
Sun, 21 Dec - Fri, 26 Dec
Multiple Airlines Logo
11:40 a.m. - 9:50 a.m.YQR-ORD
22h 10m1 stop
Multiple Airlines Logo
11:03 a.m. - 6:20 p.m.ORD-YQR
7h 17m1 stop
C$ 385Multiple Airlines
Find Deal
Sun, 21 Dec - Wed, 24 Dec
Multiple Airlines Logo
11:40 a.m. - 9:50 a.m.YQR-ORD
22h 10m1 stop
Multiple Airlines Logo
8:20 p.m. - 6:20 p.m.ORD-YQR
22h 00m1 stop
C$ 437Multiple Airlines
Find Deal
Sun, 21 Dec - Sun, 28 Dec
Multiple Airlines Logo
6:20 p.m. - 10:44 a.m.YQR-ORD
40h 24m2 stops
Multiple Airlines Logo
11:27 a.m. - 6:20 p.m.ORD-YQR
6h 53m1 stop
C$ 443Multiple Airlines
Find Deal
Tue, 16 Dec - Tue, 23 Dec
Delta Logo
11:45 a.m. - 5:56 p.m.YQR-ORD
6h 11m1 stop
Delta Logo
6:50 a.m. - 6:17 p.m.ORD-YQR
11h 27m2 stops
C$ 490Delta
Find Deal
Sat, 10 Jan - Tue, 13 Jan
Delta Logo
11:40 a.m. - 5:19 p.m.YQR-MDW
5h 39m1 stop
Delta Logo
5:59 p.m. - 6:20 p.m.MDW-YQR
24h 21m1 stop
C$ 593Delta
Find Deal
Sun, 21 Dec - Wed, 24 Dec
United Airlines Logo
10:53 a.m. - 4:58 p.m.YQR-ORD
6h 05m1 stop
United Airlines Logo
2:31 p.m. - 10:51 p.m.ORD-YQR
8h 20m1 stop
C$ 685United Airlines
Find Deal
Tue, 16 Dec - Tue, 23 Dec
WestJet Logo
12:15 p.m. - 1:35 p.m.YQR-ORD
25h 20m1 stop
WestJet Logo
6:51 p.m. - 6:21 p.m.ORD-YQR
23h 30m1 stop
C$ 768WestJet
Find Deal
Sun, 1 Feb - Sun, 22 Feb
WestJet Logo
6:10 a.m. - 1:35 p.m.YQR-ORD
7h 25m1 stop
WestJet Logo
9:50 a.m. - 5:46 p.m.ORD-YQR
31h 56m2 stops
C$ 916WestJet
Find Deal
Fri, 19 Dec - Sat, 27 Dec
Air Canada Logo
5:40 a.m. - 9:19 p.m.YQR-ORD
15h 39m2 stops
Air Canada Logo
5:52 p.m. - 10:39 a.m.ORD-YQR
16h 47m2 stops
C$ 979Air Canada
Find Deal
Fri, 19 Dec - Wed, 24 Dec

Delta flights from Regina to Chicago

Our best Delta deals on Regina to Chicago flight tickets
Delta
10 Jan
YQR11:45 a.m.Regina
6h 11m
1 stop
ORD5:56 p.m.Chicago O'Hare Intl
13 Jan
ORD6:50 a.m.Chicago O'Hare Intl
11h 27m
2 stops
YQR6:17 p.m.Regina
C$ 490
Find similar
Delta
21 Dec
YQR11:40 a.m.Regina
5h 39m
1 stop
MDW5:19 p.m.Chicago Midway
24 Dec
MDW5:59 p.m.Chicago Midway
24h 21m
1 stop
YQR6:20 p.m.Regina
C$ 593
Find similar
Delta
20 Dec
YQR11:40 a.m.Regina
9h 54m
1 stop
ORD9:34 p.m.Chicago O'Hare Intl
3 Jan
ORD10:05 a.m.Chicago O'Hare Intl
8h 12m
1 stop
YQR6:17 p.m.Regina
C$ 621
Find similar

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets
WestJet
1 Feb
YQR12:15 p.m.Regina
25h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
22 Feb
ORD6:51 p.m.Chicago O'Hare Intl
23h 30m
1 stop
YQR6:21 p.m.Regina
C$ 768
Find similar
WestJet
19 Dec
YQR6:10 a.m.Regina
7h 25m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
27 Dec
ORD9:50 a.m.Chicago O'Hare Intl
31h 56m
2 stops
YQR5:46 p.m.Regina
C$ 916
Find similar
WestJet
20 Dec
YQR11:40 a.m.Regina
5h 39m
1 stop
MDW5:19 p.m.Chicago Midway
25 Dec
MDW11:48 a.m.Chicago Midway
37h 29m
2 stops
YQR1:17 a.m.Regina
C$ 941
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Regina to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 3 November 2025.
Use the filters below to find and compare flights from Regina to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 21/12

11:40 a.m.-9:50 a.m.

1 stop22h 10m

Chicago O'Hare Intl

Fri 26/12

12:26 p.m.-6:20 p.m.

1 stop5h 54m

C$ 356

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 21/12

11:40 a.m.-9:50 a.m.

1 stop22h 10m

Chicago O'Hare Intl

Wed 24/12

11:03 a.m.-6:20 p.m.

1 stop7h 17m

C$ 385

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 21/12

11:40 a.m.-9:50 a.m.

1 stop22h 10m

Chicago O'Hare Intl

Sun 28/12

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

1 stop22h 00m

C$ 437

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 16/12

6:20 p.m.-10:44 a.m.

2 stops40h 24m

Chicago O'Hare Intl

Tue 23/12

11:27 a.m.-6:20 p.m.

1 stop6h 53m

C$ 443

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 10/1

11:45 a.m.-5:56 p.m.

1 stop6h 11m

Chicago O'Hare Intl

Tue 13/1

6:50 a.m.-6:17 p.m.

2 stops11h 27m

C$ 490

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sun 21/12

11:40 a.m.-5:19 p.m.

1 stop5h 39m

Chicago Midway

Wed 24/12

5:59 p.m.-6:20 p.m.

1 stop24h 21m

C$ 593

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 16/12

10:53 a.m.-4:58 p.m.

1 stop6h 05m

Chicago O'Hare Intl

Tue 23/12

2:31 p.m.-10:51 p.m.

1 stop8h 20m

C$ 685

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 1/2

12:15 p.m.-1:35 p.m.

1 stop25h 20m

Chicago O'Hare Intl

Sun 22/2

6:51 p.m.-6:21 p.m.

1 stop23h 30m

C$ 768

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 19/12

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

1 stop7h 25m

Chicago O'Hare Intl

Sat 27/12

9:50 a.m.-5:46 p.m.

2 stops31h 56m

C$ 916

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 19/12

5:40 a.m.-9:19 p.m.

2 stops15h 39m

Chicago O'Hare Intl

Wed 24/12

5:52 p.m.-10:39 a.m.

2 stops16h 47m

C$ 979

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Chicago from

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

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$ 409.

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 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?

  • 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?

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 CanadaPriceFrom C$ 412Free CancellationRating
7.1
10,398 reviews
Search Air Canada flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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.

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport