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Cheap flights from Regina to Chicago from C$ 280

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 10/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Regina to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
2:00 p.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
25h 40m1 stop Calgary
WestJet Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
C$ 466WestJet
Sat, 26 Sep - Tue, 29 Sep
WestJet Logo
8:20 p.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
19h 20m2 stops Edmonton Calgary
WestJet Logo
5:30 p.m. - 1:10 a.m.ORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
C$ 487WestJet
Sat, 26 Sep - Tue, 29 Sep
United Airlines Logo
9:45 a.m. - 10:46 p.m.YQR  Regina-ORD Chicago O'Hare Intl
12h 01m1 stop Denver Intl
United Airlines Logo
6:00 a.m. - 9:30 p.m.ORD  Chicago O'Hare Intl-YQR Regina
16h 30m1 stop Denver Intl
C$ 489United Airlines
Wed, 2 Sep - Tue, 8 Sep
United Airlines Logo
9:45 a.m. - 9:59 p.m.YQR  Regina-ORD Chicago O'Hare Intl
11h 14m1 stop Denver Intl
United Airlines Logo
6:00 a.m. - 9:30 p.m.ORD  Chicago O'Hare Intl-YQR Regina
16h 30m1 stop Denver Intl
C$ 489United Airlines
Tue, 1 Sep - Tue, 8 Sep
Air Canada Logo
5:45 a.m. - 2:55 p.m.YQR  Regina-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
Air Canada Logo
9:55 a.m. - 7:05 p.m.ORD  Chicago O'Hare Intl-YQR Regina
10h 10m1 stop Toronto Pearson Intl
C$ 524Air Canada
Thu, 17 Sep - Thu, 24 Sep
WestJet Logo
8:20 p.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
19h 20m2 stops Edmonton Calgary
WestJet Logo
5:30 p.m. - 7:45 p.m.ORD  Chicago O'Hare Intl-YQR Regina
27h 15m2 stops Calgary Edmonton
C$ 531WestJet
Sat, 26 Sep - Tue, 29 Sep
WestJet Logo
2:00 p.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
25h 40m1 stop Calgary
WestJet Logo
5:30 p.m. - 11:20 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
C$ 538WestJet
Thu, 1 Oct - Mon, 5 Oct
WestJet Logo
8:20 p.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
19h 20m2 stops Edmonton Calgary
WestJet Logo
5:30 p.m. - 11:20 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
C$ 538WestJet
Thu, 1 Oct - Mon, 5 Oct
WestJet Logo
9:05 p.m. - 4:40 p.m.YQR  Regina-ORD Chicago O'Hare Intl
18h 35m1 stop Calgary
WestJet Logo
5:30 p.m. - 11:20 p.m.ORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
C$ 540WestJet
Thu, 1 Oct - Mon, 5 Oct
Delta Logo
6:00 a.m. - 6:33 p.m.YQR  Regina-MDW Chicago Midway
11h 33m2 stops Calgary Detroit Metropolitan Wayne County
Delta Logo
1:19 p.m. - 11:20 p.m.MDW  Chicago Midway-YQR Regina
11h 01m2 stops Detroit Metropolitan Wayne County Calgary
C$ 544Delta
Thu, 1 Oct - Mon, 5 Oct

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Delta flights from Regina to Chicago

Our best Delta deals on Regina to Chicago flight tickets
Delta
1 Oct
YQR6:00 a.m.Regina
11h 33m
2 stops
MDW6:33 p.m.Chicago Midway
5 Oct
MDW1:19 p.m.Chicago Midway
11h 01m
2 stops
YQR11:20 p.m.Regina
C$ 544
Delta
1 Oct
YQR6:00 a.m.Regina
11h 26m
2 stops
ORD6:26 p.m.Chicago O'Hare Intl
5 Oct
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
C$ 545
Delta
2 Sep
YQR6:00 a.m.Regina
13h 30m
2 stops
ORD8:30 p.m.Chicago O'Hare Intl
8 Sep
ORD8:25 a.m.Chicago O'Hare Intl
9h 55m
1 stop
YQR5:20 p.m.Regina
C$ 608

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets
WestJet
26 Sep
YQR2:00 p.m.Regina
25h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
29 Sep
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
C$ 466
WestJet
26 Sep
YQR8:20 p.m.Regina
19h 20m
2 stops
ORD4:40 p.m.Chicago O'Hare Intl
29 Sep
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
C$ 487
WestJet
26 Sep
YQR8:20 p.m.Regina
19h 20m
2 stops
ORD4:40 p.m.Chicago O'Hare Intl
29 Sep
ORD5:30 p.m.Chicago O'Hare Intl
27h 15m
2 stops
YQR7:45 p.m.Regina
C$ 531

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 8 August 2026.
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

Cheapest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 26/9

2:00 p.m.-4:40 p.m.

1 stop25h 40m

Chicago O'Hare Intl

Tue 29/9

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

1 stop8h 40m

C$ 466

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 26/9

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

2 stops19h 20m

Chicago O'Hare Intl

Tue 29/9

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

1 stop8h 40m

C$ 487

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Wed 2/9

9:45 a.m.-10:46 p.m.

1 stop12h 01m

Chicago O'Hare Intl

Tue 8/9

6:00 a.m.-9:30 p.m.

1 stop16h 30m

C$ 489

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 1/9

9:45 a.m.-9:59 p.m.

1 stop11h 14m

Chicago O'Hare Intl

Tue 8/9

6:00 a.m.-9:30 p.m.

1 stop16h 30m

C$ 489
Quickest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 17/9

5:45 a.m.-2:55 p.m.

1 stop8h 10m

Chicago O'Hare Intl

Thu 24/9

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

1 stop10h 10m

C$ 524

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 26/9

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

2 stops19h 20m

Chicago O'Hare Intl

Tue 29/9

5:30 p.m.-7:45 p.m.

2 stops27h 15m

C$ 531

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 1/10

2:00 p.m.-4:40 p.m.

1 stop25h 40m

Chicago O'Hare Intl

Mon 5/10

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

1 stop6h 50m

C$ 538

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 1/10

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

2 stops19h 20m

Chicago O'Hare Intl

Mon 5/10

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

1 stop6h 50m

C$ 538

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 1/10

9:05 p.m.-4:40 p.m.

1 stop18h 35m

Chicago O'Hare Intl

Mon 5/10

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

1 stop6h 50m

C$ 540

ReginaChicago

YQR Regina - MDW Chicago Midway

YQRMDW

Regina

Thu 1/10

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

2 stops11h 33m

Chicago Midway

Mon 5/10

1:19 p.m.-11:20 p.m.

2 stops11h 01m

C$ 544

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?

Prices are currently low for flights on this route.

Typical prices usually range from C$ 495 to C$ 944.
The lowest price recently found on this route was C$ 466.

What is the cheapest month to fly to Chicago?

The month of November is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 487.

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

6h 34m

Direct flights

None
The fastest flight from Regina to Chicago takes 6h 34m
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 34m.

  • 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?

Travelling to a place near Chicago?

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