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Cheap flights from Regina to Chicago from $254

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 12/21. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:40 am - 9:50 amYQR-ORD
22h 10m1 stop
Multiple Airlines Logo
12:26 pm - 6:20 pmORD-YQR
5h 54m1 stop
$254Multiple Airlines
Find Deal
Sun, Dec 21 - Fri, Dec 26
Multiple Airlines Logo
11:40 am - 9:50 amYQR-ORD
22h 10m1 stop
Multiple Airlines Logo
11:03 am - 6:20 pmORD-YQR
7h 17m1 stop
$275Multiple Airlines
Find Deal
Sun, Dec 21 - Wed, Dec 24
Multiple Airlines Logo
11:40 am - 9:50 amYQR-ORD
22h 10m1 stop
Multiple Airlines Logo
8:20 pm - 6:20 pmORD-YQR
22h 00m1 stop
$312Multiple Airlines
Find Deal
Sun, Dec 21 - Sun, Dec 28
Multiple Airlines Logo
6:20 pm - 10:44 amYQR-ORD
40h 24m2 stops
Multiple Airlines Logo
11:27 am - 6:20 pmORD-YQR
6h 53m1 stop
$316Multiple Airlines
Find Deal
Tue, Dec 16 - Tue, Dec 23
Delta Logo
11:45 am - 9:42 pmYQR-ORD
9h 57m1 stop
Delta Logo
12:27 pm - 6:17 pmORD-YQR
5h 50m1 stop
$350Delta
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Sat, Jan 10 - Tue, Jan 13
Delta Logo
11:40 am - 9:34 pmYQR-ORD
9h 54m1 stop
Delta Logo
10:05 am - 6:17 pmORD-YQR
8h 12m1 stop
$443Delta
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Sat, Dec 20 - Sat, Jan 3
United Airlines Logo
10:53 am - 4:58 pmYQR-ORD
6h 05m1 stop
United Airlines Logo
2:31 pm - 10:51 pmORD-YQR
8h 20m1 stop
$489United Airlines
Find Deal
Tue, Dec 16 - Tue, Dec 23
WestJet Logo
6:10 am - 1:35 pmYQR-ORD
7h 25m1 stop
WestJet Logo
9:50 am - 5:46 pmORD-YQR
31h 56m2 stops
$654WestJet
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Fri, Dec 19 - Sat, Dec 27
WestJet Logo
11:40 am - 9:34 pmYQR-ORD
9h 54m1 stop
WestJet Logo
9:50 am - 5:46 pmORD-YQR
31h 56m2 stops
$683WestJet
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Sat, Dec 20 - Sat, Dec 27
Air Canada Logo
5:40 am - 9:19 pmYQR-ORD
15h 39m2 stops
Air Canada Logo
5:52 pm - 10:39 amORD-YQR
16h 47m2 stops
$699Air Canada
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Fri, Dec 19 - Wed, Dec 24

Delta flights from Regina to Chicago O'Hare Intl Airport

Our best Delta deals on Regina to Chicago O'Hare Intl Airport flight tickets
Delta
Jan 10
YQR11:45 amRegina
9h 57m
1 stop
ORD9:42 pmChicago O'Hare Intl
Jan 13
ORD12:27 pmChicago O'Hare Intl
5h 50m
1 stop
YQR6:17 pmRegina
$350
Find similar
Delta
Dec 20
YQR11:40 amRegina
9h 54m
1 stop
ORD9:34 pmChicago O'Hare Intl
Jan 3
ORD10:05 amChicago O'Hare Intl
8h 12m
1 stop
YQR6:17 pmRegina
$443
Find similar
Delta
Dec 20
YQR11:40 amRegina
9h 54m
1 stop
ORD9:34 pmChicago O'Hare Intl
Dec 27
ORD7:05 pmChicago O'Hare Intl
23h 15m
1 stop
YQR6:20 pmRegina
$509
Find similar

WestJet flights from Regina to Chicago O'Hare Intl Airport

Our best WestJet deals on Regina to Chicago O'Hare Intl Airport flight tickets
WestJet
Dec 19
YQR6:10 amRegina
7h 25m
1 stop
ORD1:35 pmChicago O'Hare Intl
Dec 27
ORD9:50 amChicago O'Hare Intl
31h 56m
2 stops
YQR5:46 pmRegina
$654
Find similar
WestJet
Dec 20
YQR11:40 amRegina
9h 54m
1 stop
ORD9:34 pmChicago O'Hare Intl
Dec 27
ORD9:50 amChicago O'Hare Intl
31h 56m
2 stops
YQR5:46 pmRegina
$683
Find similar
WestJet
Dec 19
YQR10:40 amRegina
11h 00m
2 stops
ORD9:40 pmChicago O'Hare Intl
Dec 26
ORD10:00 amChicago O'Hare Intl
15h 17m
2 stops
YQR1:17 amRegina
$697
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Regina to Chicago O'Hare Intl Airport 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 832,500 searches. Data last updated November 3, 2025.
Use the filters below to find and compare flights from Regina to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 12/21

11:40 am-9:50 am

1 stop22h 10m

Chicago O'Hare Intl

Fri 12/26

12:26 pm-6:20 pm

1 stop5h 54m

$254

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 12/21

11:40 am-9:50 am

1 stop22h 10m

Chicago O'Hare Intl

Wed 12/24

11:03 am-6:20 pm

1 stop7h 17m

$275

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 12/21

11:40 am-9:50 am

1 stop22h 10m

Chicago O'Hare Intl

Sun 12/28

8:20 pm-6:20 pm

1 stop22h 00m

$312

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 12/16

6:20 pm-10:44 am

2 stops40h 24m

Chicago O'Hare Intl

Tue 12/23

11:27 am-6:20 pm

1 stop6h 53m

$316

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 1/10

11:45 am-9:42 pm

1 stop9h 57m

Chicago O'Hare Intl

Tue 1/13

12:27 pm-6:17 pm

1 stop5h 50m

$350

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 12/20

11:40 am-9:34 pm

1 stop9h 54m

Chicago O'Hare Intl

Sat 1/3

10:05 am-6:17 pm

1 stop8h 12m

$443

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 12/16

10:53 am-4:58 pm

1 stop6h 05m

Chicago O'Hare Intl

Tue 12/23

2:31 pm-10:51 pm

1 stop8h 20m

$489

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 12/19

6:10 am-1:35 pm

1 stop7h 25m

Chicago O'Hare Intl

Sat 12/27

9:50 am-5:46 pm

2 stops31h 56m

$654

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 12/20

11:40 am-9:34 pm

1 stop9h 54m

Chicago O'Hare Intl

Sat 12/27

9:50 am-5:46 pm

2 stops31h 56m

$683

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 12/19

5:40 am-9:19 pm

2 stops15h 39m

Chicago O'Hare Intl

Wed 12/24

5:52 pm-10:39 am

2 stops16h 47m

$699

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 O'Hare Intl Airport

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 day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $285. This is often the case because there is less demand to fly during this day of the week. On the other hand, Thursday is the most expensive day to depart from Regina because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $590.

When to book flights from Regina to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Regina to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Regina to Chicago O'Hare Intl Airport (YQR to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Regina to Chicago O'Hare Intl Airport

Direct flights

None
There are no direct flights from Regina to Chicago O'Hare Intl Airport. There are no popular flight routes from Regina to Chicago O'Hare Intl Airport.
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  • How far is Regina to Chicago O'Hare Intl by plane?

    Regina and Chicago O'Hare Intl are 986.1 mi apart from one another. Flights usually cover this in 6h 05m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Regina Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Regina Airport to Chicago O'Hare Intl Airport were last updated today.

  • How old do you have to be to fly from Regina Airport to Chicago O'Hare Intl Airport?

    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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
Benton Harbor

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?

momondo does allow users to show only those flights to Chicago from Regina which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Regina to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Regina to Chicago.

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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