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Cheap flights from Regina to Chicago from C$ 283

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 10/9. 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
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 481WestJet
Fri, 11 Sep - Mon, 21 Sep
United Airlines Logo
9:45 a.m. - 11:59 p.m.
YQR
-
ORD
13h 14m
1 stop
United Airlines Logo
6:00 a.m. - 9:30 p.m.
ORD
-
YQR
16h 30m
1 stop
C$ 482United Airlines
Sat, 15 Aug - Sat, 22 Aug
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 486WestJet
Fri, 25 Sep - Mon, 28 Sep
United Airlines Logo
9:45 a.m. - 6:30 p.m.
YQR
-
ORD
7h 45m
1 stop
United Airlines Logo
6:00 a.m. - 9:30 p.m.
ORD
-
YQR
16h 30m
1 stop
C$ 533United Airlines
Tue, 13 Oct - Sat, 17 Oct
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 11:15 a.m.
ORD
-
YQR
18h 45m
2 stops
C$ 545WestJet
Fri, 11 Sep - Mon, 21 Sep
United Airlines Logo
10:45 a.m. - 11:59 p.m.
YQR
-
ORD
12h 14m
1 stop
United Airlines Logo
1:05 p.m. - 10:40 p.m.
ORD
-
YQR
9h 35m
1 stop
C$ 548United Airlines
Sun, 25 Oct - Wed, 4 Nov
Multiple Airlines Logo
6:00 a.m. - 7:48 p.m.
YQR
-
ORD
12h 48m
1 stop
Multiple Airlines Logo
3:40 p.m. - 9:00 a.m.
ORD
-
YQR
18h 20m
2 stops
C$ 569Multiple Airlines
Tue, 8 Sep - Tue, 15 Sep
Multiple Airlines Logo
6:00 a.m. - 7:48 p.m.
YQR
-
ORD
12h 48m
1 stop
Multiple Airlines Logo
3:40 p.m. - 3:40 p.m.
ORD
-
YQR
25h 00m
3 stops
C$ 572Multiple Airlines
Tue, 8 Sep - Tue, 15 Sep
Delta Logo
7:00 a.m. - 6:00 p.m.
YQR
-
MDW
10h 00m
2 stops
Delta Logo
10:01 a.m. - 5:20 p.m.
MDW
-
YQR
8h 19m
1 stop
C$ 600Delta
Tue, 13 Oct - Sat, 17 Oct
Delta Logo
10:45 a.m. - 10:25 p.m.
YQR
-
MDW
10h 40m
2 stops
Delta Logo
9:29 a.m. - 6:21 p.m.
MDW
-
YQR
9h 52m
2 stops
C$ 620Delta
Tue, 20 Oct - Tue, 27 Oct

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United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets
United Airlines
15 Aug
YQR9:45 a.m.Regina
13h 14m
1 stop
ORD11:59 p.m.Chicago O'Hare Intl
22 Aug
ORD6:00 a.m.Chicago O'Hare Intl
16h 30m
1 stop
YQR9:30 p.m.Regina
C$ 482
United Airlines
13 Oct
YQR9:45 a.m.Regina
7h 45m
1 stop
ORD6:30 p.m.Chicago O'Hare Intl
17 Oct
ORD6:00 a.m.Chicago O'Hare Intl
16h 30m
1 stop
YQR9:30 p.m.Regina
C$ 533
United Airlines
25 Oct
YQR10:45 a.m.Regina
12h 14m
1 stop
ORD11:59 p.m.Chicago O'Hare Intl
4 Nov
ORD1:05 p.m.Chicago O'Hare Intl
9h 35m
1 stop
YQR10:40 p.m.Regina
C$ 548

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets
WestJet
11 Sep
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
21 Sep
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
C$ 480
WestJet
25 Sep
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
28 Sep
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
C$ 486
WestJet
11 Sep
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
21 Sep
ORD5:30 p.m.Chicago O'Hare Intl
18h 45m
2 stops
YQR11:15 a.m.Regina
C$ 545

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 July 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
Quickest round-trip

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 11/9

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Mon 21/9

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

1 stop8h 40m

C$ 480

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 15/8

9:45 a.m.-11:59 p.m.

1 stop13h 14m

Chicago O'Hare Intl

Sat 22/8

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

1 stop16h 30m

C$ 482

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 25/9

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Mon 28/9

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

1 stop8h 40m

C$ 486

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 13/10

9:45 a.m.-6:30 p.m.

1 stop7h 45m

Chicago O'Hare Intl

Sat 17/10

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

1 stop16h 30m

C$ 533

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 11/9

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Mon 21/9

5:30 p.m.-11:15 a.m.

2 stops18h 45m

C$ 545

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 25/10

10:45 a.m.-11:59 p.m.

1 stop12h 14m

Chicago O'Hare Intl

Wed 4/11

1:05 p.m.-10:40 p.m.

1 stop9h 35m

C$ 548

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 8/9

6:00 a.m.-7:48 p.m.

1 stop12h 48m

Chicago O'Hare Intl

Tue 15/9

3:40 p.m.-9:00 a.m.

2 stops18h 20m

C$ 569

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 8/9

6:00 a.m.-7:48 p.m.

1 stop12h 48m

Chicago O'Hare Intl

Tue 15/9

3:40 p.m.-3:40 p.m.

3 stops25h 00m

C$ 572

ReginaChicago

YQR - MDW

YQRMDW

Regina

Tue 13/10

7:00 a.m.-6:00 p.m.

2 stops10h 00m

Chicago Midway

Sat 17/10

10:01 a.m.-5:20 p.m.

1 stop8h 19m

C$ 600

ReginaChicago

YQR - MDW

YQRMDW

Regina

Tue 20/10

10:45 a.m.-10:25 p.m.

2 stops10h 40m

Chicago Midway

Tue 27/10

9:29 a.m.-6:21 p.m.

2 stops9h 52m

C$ 620

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$ 515 to C$ 857.
The lowest price recently found on this route was C$ 480.

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$ 447.

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.
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 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