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Cheap flights from Regina to Chicago from C$ 172

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 7/1. 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
6:10 a.m. - 1:35 p.m.YQR-ORD
7h 25m1 stop
WestJet Logo
2:20 p.m. - 9:08 p.m.ORD-YQR
6h 48m1 stop
C$ 319WestJet
Find Deal
Fri, 23 Jan - Fri, 30 Jan
WestJet Logo
6:10 a.m. - 1:35 p.m.YQR-ORD
7h 25m1 stop
WestJet Logo
2:20 p.m. - 10:30 a.m.ORD-YQR
44h 10m2 stops
C$ 406WestJet
Find Deal
Fri, 23 Jan - Fri, 30 Jan
WestJet Logo
6:10 a.m. - 1:35 p.m.YQR-ORD
7h 25m1 stop
WestJet Logo
2:20 p.m. - 10:32 a.m.ORD-YQR
44h 12m2 stops
C$ 446WestJet
Find Deal
Fri, 16 Jan - Fri, 23 Jan
Delta Logo
11:45 a.m. - 11:56 p.m.YQR-ORD
12h 11m2 stops
Delta Logo
8:50 a.m. - 6:20 p.m.ORD-YQR
9h 30m1 stop
C$ 470Delta
Find Deal
Sun, 25 Jan - Thu, 29 Jan
Delta Logo
11:45 a.m. - 6:36 p.m.YQR-MDW
6h 51m1 stop
Delta Logo
9:50 a.m. - 6:20 p.m.MDW-YQR
8h 30m1 stop
C$ 470Delta
Find Deal
Mon, 26 Jan - Fri, 30 Jan
United Airlines Logo
10:45 a.m. - 9:45 a.m.YQR-ORD
23h 00m2 stops
United Airlines Logo
7:00 a.m. - 10:51 p.m.ORD-YQR
15h 51m1 stop
C$ 480United Airlines
Find Deal
Sun, 25 Jan - Thu, 29 Jan
Delta Logo
11:45 a.m. - 6:36 p.m.YQR-MDW
6h 51m1 stop
Delta Logo
9:50 a.m. - 6:20 p.m.MDW-YQR
8h 30m1 stop
C$ 490Delta
Find Deal
Fri, 23 Jan - Fri, 30 Jan
Air Canada Logo
5:00 a.m. - 7:45 p.m.YQR-ORD
14h 45m1 stop
Air Canada Logo
6:28 p.m. - 10:39 a.m.ORD-YQR
16h 11m1 stop
C$ 556Air Canada
Find Deal
Sun, 25 Jan - Thu, 29 Jan
Air Canada Logo
5:00 a.m. - 4:40 p.m.YQR-ORD
11h 40m1 stop
Air Canada Logo
6:28 p.m. - 10:39 a.m.ORD-YQR
16h 11m1 stop
C$ 575Air Canada
Find Deal
Sun, 25 Jan - Thu, 29 Jan
Multiple Airlines Logo
7:15 a.m. - 11:20 a.m.YQR-MDW
27h 05m1 stop
Multiple Airlines Logo
10:49 a.m. - 12:15 a.m.MDW-YQR
14h 26m2 stops
C$ 589Multiple Airlines
Find Deal
Thu, 12 Mar - Sun, 15 Mar

Delta flights from Regina to Chicago

Our best Delta deals on Regina to Chicago flight tickets
Delta
25 Jan
YQR11:45 a.m.Regina
12h 11m
2 stops
ORD11:56 p.m.Chicago O'Hare Intl
29 Jan
ORD8:50 a.m.Chicago O'Hare Intl
9h 30m
1 stop
YQR6:20 p.m.Regina
C$ 470
Find similar
Delta
23 Jan
YQR11:45 a.m.Regina
6h 51m
1 stop
MDW6:36 p.m.Chicago Midway
30 Jan
MDW9:50 a.m.Chicago Midway
8h 30m
1 stop
YQR6:20 p.m.Regina
C$ 490
Find similar
Delta
16 Jan
YQR11:45 a.m.Regina
12h 14m
2 stops
ORD11:59 p.m.Chicago O'Hare Intl
23 Jan
ORD6:50 a.m.Chicago O'Hare Intl
11h 30m
2 stops
YQR6:20 p.m.Regina
C$ 491
Find similar

Air Canada flights from Regina to Chicago

Our best Air Canada deals on Regina to Chicago flight tickets
Air Canada
25 Jan
YQR5:00 a.m.Regina
14h 45m
1 stop
ORD7:45 p.m.Chicago O'Hare Intl
29 Jan
ORD6:28 p.m.Chicago O'Hare Intl
16h 11m
1 stop
YQR10:39 a.m.Regina
C$ 556
Find similar
Air Canada
25 Jan
YQR5:00 a.m.Regina
11h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
29 Jan
ORD6:28 p.m.Chicago O'Hare Intl
16h 11m
1 stop
YQR10:39 a.m.Regina
C$ 575
Find similar
Air Canada
25 Jan
YQR5:00 a.m.Regina
13h 55m
2 stops
ORD6:55 p.m.Chicago O'Hare Intl
29 Jan
ORD1:00 p.m.Chicago O'Hare Intl
10h 19m
2 stops
YQR11:19 p.m.Regina
C$ 733
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 December 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

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$ 319

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$ 406

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$ 446

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 25/1

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

2 stops12h 11m

Chicago O'Hare Intl

Thu 29/1

8:50 a.m.-6:20 p.m.

1 stop9h 30m

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.-6:20 p.m.

1 stop8h 30m

C$ 470

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 25/1

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

2 stops23h 00m

Chicago O'Hare Intl

Thu 29/1

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

1 stop15h 51m

C$ 480

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$ 490

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 25/1

5:00 a.m.-7:45 p.m.

1 stop14h 45m

Chicago O'Hare Intl

Thu 29/1

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

1 stop16h 11m

C$ 556

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 25/1

5:00 a.m.-4:40 p.m.

1 stop11h 40m

Chicago O'Hare Intl

Thu 29/1

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

1 stop16h 11m

C$ 575

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 12/3

7:15 a.m.-11:20 a.m.

1 stop27h 05m

Chicago Midway

Sun 15/3

10:49 a.m.-12:15 a.m.

2 stops14h 26m

C$ 589

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 typical price of a round-trip flight between Regina and Chicago?

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$ 375.

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$ 410. 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$ 962. 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$ 468. 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$ 708 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 34m

Direct flights

None
The fastest flight from Regina to Chicago takes 5h 34m
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 55m.

  • 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
10,500 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