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Cheap flights from Regina to Chicago from C$ 207

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 9/1. 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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Find the cheapest flights from Regina to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
1:10 p.m. - 1:35 p.m.YQR-ORD
23h 25m1 stop
WestJet Logo
5:30 p.m. - 11:02 p.m.ORD-YQR
6h 32m1 stop
C$ 316WestJet
Find Deal
Thu, 16 Apr - Wed, 17 Jun
WestJet Logo
5:10 p.m. - 1:35 p.m.YQR-ORD
19h 25m2 stops
WestJet Logo
5:30 p.m. - 11:02 p.m.ORD-YQR
6h 32m1 stop
C$ 319WestJet
Find Deal
Thu, 16 Apr - Wed, 17 Jun
Delta Logo
11:45 a.m. - 6:36 p.m.YQR-MDW
6h 51m1 stop
Delta Logo
9:50 a.m. - 6:17 p.m.MDW-YQR
8h 27m1 stop
C$ 470Delta
Find Deal
Mon, 26 Jan - Fri, 30 Jan
Delta Logo
11:45 a.m. - 6:36 p.m.YQR-MDW
6h 51m1 stop
Delta Logo
9:50 a.m. - 6:17 p.m.MDW-YQR
8h 27m1 stop
C$ 491Delta
Find Deal
Mon, 26 Jan - Fri, 30 Jan
Delta Logo
11:45 a.m. - 6:36 p.m.YQR-MDW
6h 51m1 stop
Delta Logo
1:26 p.m. - 1:17 a.m.MDW-YQR
11h 51m2 stops
C$ 501Delta
Find Deal
Mon, 26 Jan - Fri, 30 Jan
Delta Logo
11:40 a.m. - 7:55 p.m.YQR-ORD
8h 15m1 stop
Delta Logo
11:00 a.m. - 6:20 p.m.ORD-YQR
7h 20m1 stop
C$ 580Delta
Find Deal
Mon, 8 Dec - Fri, 12 Dec
Air Canada Logo
5:00 a.m. - 6:33 p.m.YQR-ORD
12h 33m2 stops
Air Canada Logo
8:40 a.m. - 6:13 p.m.ORD-YQR
10h 33m2 stops
C$ 736Air Canada
Find Deal
Thu, 16 Apr - Wed, 17 Jun
WestJet Logo
6:10 a.m. - 1:35 p.m.YQR-ORD
7h 25m1 stop
WestJet Logo
2:20 p.m. - 9:15 p.m.ORD-YQR
6h 55m1 stop
C$ 810WestJet
Find Deal
Mon, 8 Dec - Fri, 12 Dec
United Airlines Logo
10:53 a.m. - 11:59 p.m.YQR-ORD
13h 06m1 stop
United Airlines Logo
8:15 p.m. - 10:39 a.m.ORD-YQR
14h 24m1 stop
C$ 1,043United Airlines
Find Deal
Wed, 24 Dec - Sun, 28 Dec
United Airlines Logo
10:53 a.m. - 11:59 p.m.YQR-ORD
13h 06m1 stop
United Airlines Logo
8:02 p.m. - 10:51 p.m.ORD-YQR
26h 49m2 stops
C$ 1,089United Airlines
Find Deal
Wed, 24 Dec - Sun, 28 Dec

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets
WestJet
16 Apr
YQR1:10 p.m.Regina
23h 25m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
17 Jun
ORD5:30 p.m.Chicago O'Hare Intl
6h 32m
1 stop
YQR11:02 p.m.Regina
C$ 316
Find similar
WestJet
16 Apr
YQR5:10 p.m.Regina
19h 25m
2 stops
ORD1:35 p.m.Chicago O'Hare Intl
17 Jun
ORD5:30 p.m.Chicago O'Hare Intl
6h 32m
1 stop
YQR11:02 p.m.Regina
C$ 319
Find similar
WestJet
8 Dec
YQR6:10 a.m.Regina
7h 25m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
12 Dec
ORD2:20 p.m.Chicago O'Hare Intl
6h 55m
1 stop
YQR9:15 p.m.Regina
C$ 810
Find similar

United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets
United Airlines
1 Dec
YQR10:45 a.m.Regina
8h 08m
1 stop
ORD6:53 p.m.Chicago O'Hare Intl
20 Dec
ORD1:48 p.m.Chicago O'Hare Intl
9h 03m
1 stop
YQR10:51 p.m.Regina
C$ 945
Find similar
United Airlines
24 Dec
YQR10:53 a.m.Regina
13h 06m
1 stop
ORD11:59 p.m.Chicago O'Hare Intl
28 Dec
ORD8:15 p.m.Chicago O'Hare Intl
14h 24m
1 stop
YQR10:39 a.m.Regina
C$ 1,043
Find similar
United Airlines
24 Dec
YQR10:53 a.m.Regina
13h 06m
1 stop
ORD11:59 p.m.Chicago O'Hare Intl
28 Dec
ORD8:02 p.m.Chicago O'Hare Intl
26h 49m
2 stops
YQR10:51 p.m.Regina
C$ 1,089
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 26 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

Thu 16/4

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

1 stop23h 25m

Chicago O'Hare Intl

Wed 17/6

5:30 p.m.-11:02 p.m.

1 stop6h 32m

C$ 316

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 16/4

5:10 p.m.-1:35 p.m.

2 stops19h 25m

Chicago O'Hare Intl

Wed 17/6

5:30 p.m.-11:02 p.m.

1 stop6h 32m

C$ 319

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.-6:17 p.m.

1 stop8h 27m

C$ 470

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.-6:17 p.m.

1 stop8h 27m

C$ 491

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 26/1

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

1 stop6h 51m

Chicago Midway

Fri 30/1

1:26 p.m.-1:17 a.m.

2 stops11h 51m

C$ 501

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 8/12

11:40 a.m.-7:55 p.m.

1 stop8h 15m

Chicago O'Hare Intl

Fri 12/12

11:00 a.m.-6:20 p.m.

1 stop7h 20m

C$ 580

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 16/4

5:00 a.m.-6:33 p.m.

2 stops12h 33m

Chicago O'Hare Intl

Wed 17/6

8:40 a.m.-6:13 p.m.

2 stops10h 33m

C$ 736

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 8/12

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

1 stop7h 25m

Chicago O'Hare Intl

Fri 12/12

2:20 p.m.-9:15 p.m.

1 stop6h 55m

C$ 810

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 24/12

10:53 a.m.-11:59 p.m.

1 stop13h 06m

Chicago O'Hare Intl

Sun 28/12

8:15 p.m.-10:39 a.m.

1 stop14h 24m

C$ 1,043

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 24/12

10:53 a.m.-11:59 p.m.

1 stop13h 06m

Chicago O'Hare Intl

Sun 28/12

8:02 p.m.-10:51 p.m.

2 stops26h 49m

C$ 1,089

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
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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 September is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 378.

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$ 414. 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$ 971. 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$ 472. 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$ 714 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

5h 20m

Direct flights

None
The fastest flight from Regina to Chicago takes 5h 20m
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 20m.

  • 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$ 415Free CancellationRating
7.1
10,481 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