Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Regina to Chicago from C$ 356

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 21/12. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Regina to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:40 a.m. - 9:50 a.m.YQR-ORD
22h 10m1 stop
Multiple Airlines Logo
12:26 p.m. - 6:20 p.m.ORD-YQR
5h 54m1 stop
C$ 356Multiple Airlines
Find Deal
Sun, 21 Dec - Fri, 26 Dec
Multiple Airlines Logo
11:40 a.m. - 9:50 a.m.YQR-ORD
22h 10m1 stop
Multiple Airlines Logo
11:03 a.m. - 6:20 p.m.ORD-YQR
7h 17m1 stop
C$ 385Multiple Airlines
Find Deal
Sun, 21 Dec - Wed, 24 Dec
Multiple Airlines Logo
11:40 a.m. - 9:50 a.m.YQR-ORD
22h 10m1 stop
Multiple Airlines Logo
8:20 p.m. - 6:20 p.m.ORD-YQR
22h 00m1 stop
C$ 437Multiple Airlines
Find Deal
Sun, 21 Dec - Sun, 28 Dec
Multiple Airlines Logo
6:20 p.m. - 10:44 a.m.YQR-ORD
40h 24m2 stops
Multiple Airlines Logo
11:27 a.m. - 6:20 p.m.ORD-YQR
6h 53m1 stop
C$ 443Multiple Airlines
Find Deal
Tue, 16 Dec - Tue, 23 Dec
Delta Logo
11:45 a.m. - 5:56 p.m.YQR-ORD
6h 11m1 stop
Delta Logo
6:50 a.m. - 6:17 p.m.ORD-YQR
11h 27m2 stops
C$ 490Delta
Find Deal
Sat, 10 Jan - Tue, 13 Jan
Delta Logo
11:40 a.m. - 9:34 p.m.YQR-ORD
9h 54m1 stop
Delta Logo
10:05 a.m. - 6:17 p.m.ORD-YQR
8h 12m1 stop
C$ 621Delta
Find Deal
Sat, 20 Dec - Sat, 3 Jan
United Airlines Logo
10:53 a.m. - 4:58 p.m.YQR-ORD
6h 05m1 stop
United Airlines Logo
2:31 p.m. - 10:51 p.m.ORD-YQR
8h 20m1 stop
C$ 685United Airlines
Find Deal
Tue, 16 Dec - Tue, 23 Dec
WestJet Logo
12:15 p.m. - 1:35 p.m.YQR-ORD
25h 20m1 stop
WestJet Logo
6:51 p.m. - 6:21 p.m.ORD-YQR
23h 30m1 stop
C$ 768WestJet
Find Deal
Sun, 1 Feb - Sun, 22 Feb
WestJet Logo
6:10 a.m. - 1:35 p.m.YQR-ORD
7h 25m1 stop
WestJet Logo
9:50 a.m. - 5:46 p.m.ORD-YQR
31h 56m2 stops
C$ 916WestJet
Find Deal
Fri, 19 Dec - Sat, 27 Dec
Air Canada Logo
5:40 a.m. - 9:19 p.m.YQR-ORD
15h 39m2 stops
Air Canada Logo
5:52 p.m. - 10:39 a.m.ORD-YQR
16h 47m2 stops
C$ 979Air Canada
Find Deal
Fri, 19 Dec - Wed, 24 Dec

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
10 Jan
YQR11:45 a.m.Regina
6h 11m
1 stop
ORD5:56 p.m.Chicago O'Hare Intl
13 Jan
ORD6:50 a.m.Chicago O'Hare Intl
11h 27m
2 stops
YQR6:17 p.m.Regina
C$ 490
Find similar
Delta
20 Dec
YQR11:40 a.m.Regina
9h 54m
1 stop
ORD9:34 p.m.Chicago O'Hare Intl
3 Jan
ORD10:05 a.m.Chicago O'Hare Intl
8h 12m
1 stop
YQR6:17 p.m.Regina
C$ 621
Find similar
Delta
20 Dec
YQR11:40 a.m.Regina
9h 54m
1 stop
ORD9:34 p.m.Chicago O'Hare Intl
27 Dec
ORD7:05 p.m.Chicago O'Hare Intl
23h 15m
1 stop
YQR6:20 p.m.Regina
C$ 713
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
1 Feb
YQR12:15 p.m.Regina
25h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
22 Feb
ORD6:51 p.m.Chicago O'Hare Intl
23h 30m
1 stop
YQR6:21 p.m.Regina
C$ 768
Find similar
WestJet
19 Dec
YQR6:10 a.m.Regina
7h 25m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
27 Dec
ORD9:50 a.m.Chicago O'Hare Intl
31h 56m
2 stops
YQR5:46 p.m.Regina
C$ 916
Find similar
WestJet
20 Dec
YQR11:40 a.m.Regina
9h 54m
1 stop
ORD9:34 p.m.Chicago O'Hare Intl
27 Dec
ORD9:50 a.m.Chicago O'Hare Intl
31h 56m
2 stops
YQR5:46 p.m.Regina
C$ 957
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 96,600 searches. Data last updated 3 November 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 21/12

11:40 a.m.-9:50 a.m.

1 stop22h 10m

Chicago O'Hare Intl

Fri 26/12

12:26 p.m.-6:20 p.m.

1 stop5h 54m

C$ 356

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 21/12

11:40 a.m.-9:50 a.m.

1 stop22h 10m

Chicago O'Hare Intl

Wed 24/12

11:03 a.m.-6:20 p.m.

1 stop7h 17m

C$ 385

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 21/12

11:40 a.m.-9:50 a.m.

1 stop22h 10m

Chicago O'Hare Intl

Sun 28/12

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

1 stop22h 00m

C$ 437

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 16/12

6:20 p.m.-10:44 a.m.

2 stops40h 24m

Chicago O'Hare Intl

Tue 23/12

11:27 a.m.-6:20 p.m.

1 stop6h 53m

C$ 443

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 10/1

11:45 a.m.-5:56 p.m.

1 stop6h 11m

Chicago O'Hare Intl

Tue 13/1

6:50 a.m.-6:17 p.m.

2 stops11h 27m

C$ 490

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 20/12

11:40 a.m.-9:34 p.m.

1 stop9h 54m

Chicago O'Hare Intl

Sat 3/1

10:05 a.m.-6:17 p.m.

1 stop8h 12m

C$ 621

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 16/12

10:53 a.m.-4:58 p.m.

1 stop6h 05m

Chicago O'Hare Intl

Tue 23/12

2:31 p.m.-10:51 p.m.

1 stop8h 20m

C$ 685

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 1/2

12:15 p.m.-1:35 p.m.

1 stop25h 20m

Chicago O'Hare Intl

Sun 22/2

6:51 p.m.-6:21 p.m.

1 stop23h 30m

C$ 768

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 19/12

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

1 stop7h 25m

Chicago O'Hare Intl

Sat 27/12

9:50 a.m.-5:46 p.m.

2 stops31h 56m

C$ 916

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 19/12

5:40 a.m.-9:19 p.m.

2 stops15h 39m

Chicago O'Hare Intl

Wed 24/12

5:52 p.m.-10:39 a.m.

2 stops16h 47m

C$ 979

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 Saturday when prices can be found for as low as C$ 512. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Regina to Chicago O'Hare Intl Airport for around C$ 819.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the afternoon is the cheapest time of day to fly from Regina to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 469. Flying to Chicago O'Hare Intl Airport in the afternoon is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 678 on average. Flights to Chicago O'Hare Intl Airport from Regina at noon are generally more expensive because this time of day is more convenient for travellers’ schedules.

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.
Search flight deals

  • How far is Regina to Chicago O'Hare Intl by plane?

    Regina and Chicago O'Hare Intl are 1586.9 km apart from one another. Typically, this will take 6h 05m by plane in normal conditions.

  • 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 are refreshed on a daily basis.

  • How many operators does momondo search for flights from Regina Airport to Chicago O'Hare Intl Airport?

  • 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 offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify 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 necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Regina to Chicago O'Hare Intl Airport?

Best airlines flying from Regina to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Regina to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 412Free CancellationRating
7.1
10,392 reviews
Search Air Canada flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Schaumburg
Rosemont
Hoffman Estates
Northbrook
Tinley Park
Munster
Hammond
Naperville
Glenview
Great Lakes
Wheeling
Des Plaines
Elk Grove Village
Harvard
Merrillville
Oak Brook
Elmhurst
Kenosha
Skokie
Rockford

Why use momondo?

Why should I use momondo to find a flight deal from Regina to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Regina to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Regina to Chicago with flexible booking policies on momondo?

Flights from Regina to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo helps you find the best flight between Regina and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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.

An easier way to manage your Chicago O'Hare Intl Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 3/12
Wed 10/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago