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Cheap flights from Regina to Chicago from C$ 176

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 28/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Regina to Chicago

Cheap round-trip flights

WestJet Logo
6:55 a.m. - 4:43 p.m.YQR-ORD
8h 48m1 stop
WestJet Logo
5:30 p.m. - 11:01 p.m.ORD-YQR
6h 31m1 stop
C$ 245WestJet
Find Deal
Thu, 16 Oct - Sat, 18 Oct
WestJet Logo
6:55 a.m. - 4:43 p.m.YQR-ORD
8h 48m1 stop
WestJet Logo
5:30 p.m. - 8:05 p.m.ORD-YQR
27h 35m1 stop
C$ 282WestJet
Find Deal
Fri, 17 Oct - Sun, 19 Oct
United Airlines Logo
11:25 a.m. - 7:24 p.m.YQR-ORD
6h 59m1 stop
United Airlines Logo
7:10 a.m. - 9:51 p.m.ORD-YQR
15h 41m1 stop
C$ 292United Airlines
Find Deal
Wed, 15 Oct - Wed, 29 Oct
United Airlines Logo
9:45 a.m. - 10:39 p.m.YQR-ORD
11h 54m1 stop
United Airlines Logo
2:53 p.m. - 9:36 p.m.ORD-YQR
7h 43m1 stop
C$ 298United Airlines
Find Deal
Mon, 20 Oct - Fri, 24 Oct
WestJet Logo
6:55 a.m. - 4:43 p.m.YQR-ORD
8h 48m1 stop
WestJet Logo
5:30 p.m. - 11:26 a.m.ORD-YQR
18h 56m2 stops
C$ 328WestJet
Find Deal
Fri, 17 Oct - Sun, 19 Oct
Logo
10:15 a.m. - 6:39 p.m.YQR-ORD
7h 24m1 stop
Logo
5:30 p.m. - 5:01 p.m.ORD-YQR
24h 31m2 stops
C$ 358
Find Deal
Mon, 20 Oct - Fri, 24 Oct
WestJet Logo
3:55 p.m. - 4:43 p.m.YQR-ORD
23h 48m2 stops
WestJet Logo
5:30 p.m. - 11:01 p.m.ORD-YQR
6h 31m1 stop
C$ 364WestJet
Find Deal
Thu, 16 Oct - Sat, 18 Oct
Delta Logo
6:00 a.m. - 8:23 p.m.YQR-ORD
13h 23m2 stops
Delta Logo
6:45 a.m. - 6:20 p.m.ORD-YQR
12h 35m2 stops
C$ 458Delta
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Wed, 15 Oct - Wed, 29 Oct
Logo
10:05 a.m. - 12:31 p.m.YQR-ORD
25h 26m3 stops
Logo
7:43 p.m. - 12:17 a.m.ORD-YQR
29h 34m2 stops
C$ 514
Find Deal
Wed, 15 Oct - Wed, 29 Oct
Air Canada Logo
2:25 p.m. - 8:00 a.m.YQR-ORD
16h 35m2 stops
Air Canada Logo
8:40 a.m. - 6:13 p.m.ORD-YQR
10h 33m2 stops
C$ 929Air Canada
Find Deal
Mon, 20 Oct - Fri, 24 Oct

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
16 Oct
YQR6:55 a.m.Regina
8h 48m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
18 Oct
ORD5:30 p.m.Chicago O'Hare Intl
6h 31m
1 stop
YQR11:01 p.m.Regina
C$ 245
Find similar
WestJet
17 Oct
YQR6:55 a.m.Regina
8h 48m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
19 Oct
ORD5:30 p.m.Chicago O'Hare Intl
27h 35m
1 stop
YQR8:05 p.m.Regina
C$ 282
Find similar
WestJet
17 Oct
YQR6:55 a.m.Regina
8h 48m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
19 Oct
ORD5:30 p.m.Chicago O'Hare Intl
18h 56m
2 stops
YQR11:26 a.m.Regina
C$ 328
Find similar

United Airlines flights from Regina to Chicago O'Hare Intl Airport

Our best United Airlines deals on Regina to Chicago O'Hare Intl Airport flight tickets
United Airlines
15 Oct
YQR11:25 a.m.Regina
6h 59m
1 stop
ORD7:24 p.m.Chicago O'Hare Intl
29 Oct
ORD7:10 a.m.Chicago O'Hare Intl
15h 41m
1 stop
YQR9:51 p.m.Regina
C$ 292
Find similar
United Airlines
20 Oct
YQR9:45 a.m.Regina
11h 54m
1 stop
ORD10:39 p.m.Chicago O'Hare Intl
24 Oct
ORD2:53 p.m.Chicago O'Hare Intl
7h 43m
1 stop
YQR9:36 p.m.Regina
C$ 298
Find similar
United Airlines
18 Dec
YQR10:53 a.m.Regina
8h 02m
1 stop
ORD6:55 p.m.Chicago O'Hare Intl
23 Dec
ORD4:50 p.m.Chicago O'Hare Intl
6h 29m
1 stop
YQR11:19 p.m.Regina
C$ 660
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 15 September 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

Thu 16/10

6:55 a.m.-4:43 p.m.

1 stop8h 48m

Chicago O'Hare Intl

Sat 18/10

5:30 p.m.-11:01 p.m.

1 stop6h 31m

C$ 245

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 17/10

6:55 a.m.-4:43 p.m.

1 stop8h 48m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-8:05 p.m.

1 stop27h 35m

C$ 282

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 15/10

11:25 a.m.-7:24 p.m.

1 stop6h 59m

Chicago O'Hare Intl

Wed 29/10

7:10 a.m.-9:51 p.m.

1 stop15h 41m

C$ 292

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 20/10

9:45 a.m.-10:39 p.m.

1 stop11h 54m

Chicago O'Hare Intl

Fri 24/10

2:53 p.m.-9:36 p.m.

1 stop7h 43m

C$ 298

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 17/10

6:55 a.m.-4:43 p.m.

1 stop8h 48m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-11:26 a.m.

2 stops18h 56m

C$ 328

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 20/10

10:15 a.m.-6:39 p.m.

1 stop7h 24m

Chicago O'Hare Intl

Fri 24/10

5:30 p.m.-5:01 p.m.

2 stops24h 31m

C$ 358

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 16/10

3:55 p.m.-4:43 p.m.

2 stops23h 48m

Chicago O'Hare Intl

Sat 18/10

5:30 p.m.-11:01 p.m.

1 stop6h 31m

C$ 364

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 15/10

6:00 a.m.-8:23 p.m.

2 stops13h 23m

Chicago O'Hare Intl

Wed 29/10

6:45 a.m.-6:20 p.m.

2 stops12h 35m

C$ 458

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 15/10

10:05 a.m.-12:31 p.m.

3 stops25h 26m

Chicago O'Hare Intl

Wed 29/10

7:43 p.m.-12:17 a.m.

2 stops29h 34m

C$ 514

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 20/10

2:25 p.m.-8:00 a.m.

2 stops16h 35m

Chicago O'Hare Intl

Fri 24/10

8:40 a.m.-6:13 p.m.

2 stops10h 33m

C$ 929

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Regina and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

In general, September is the cheapest month to fly from Regina to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 389. The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Regina averaging around C$ 469.

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$ 506. 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$ 809.

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$ 463. 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$ 670 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.
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  • 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 59m 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
WestJetPriceFrom C$ 374Free CancellationRating
7.2
3,091 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 401Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
DeltaPriceFrom C$ 465Free CancellationRating
7.9
7,954 reviews
Search Delta flights

Travelling to a place near Chicago?

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

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.

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