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Cheap flights from Regina to Chicago from C$ 207

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 16/4. 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

Enter your travel dates to find the best prices.
WestJet Logo
4:25 p.m. - 1:35 p.m.
YQR
-
ORD
21h 10m1 stop
WestJet Logo
2:20 p.m. - 9:06 p.m.
ORD
-
YQR
6h 46m1 stop
C$ 302WestJet
Thu, 5 Feb - Mon, 9 Feb
United Airlines Logo
10:45 a.m. - 11:59 p.m.
YQR
-
ORD
13h 14m1 stop
United Airlines Logo
7:10 a.m. - 10:51 p.m.
ORD
-
YQR
15h 41m1 stop
C$ 306United Airlines
Sat, 10 Jan - Wed, 4 Mar
WestJet Logo
7:05 a.m. - 1:35 p.m.
YQR
-
ORD
30h 30m2 stops
WestJet Logo
2:20 p.m. - 9:06 p.m.
ORD
-
YQR
6h 46m1 stop
C$ 405WestJet
Thu, 5 Feb - Mon, 9 Feb
WestJet Logo
6:10 p.m. - 1:35 p.m.
YQR
-
ORD
19h 25m2 stops
WestJet Logo
2:20 p.m. - 10:32 a.m.
ORD
-
YQR
44h 12m2 stops
C$ 413WestJet
Thu, 5 Feb - Mon, 9 Feb
United Airlines Logo
10:45 a.m. - 6:46 p.m.
YQR
-
ORD
8h 01m1 stop
United Airlines Logo
7:25 a.m. - 10:51 p.m.
ORD
-
YQR
15h 26m2 stops
C$ 478United Airlines
Sat, 10 Jan - Wed, 4 Mar
United Airlines Logo
10:45 a.m. - 6:46 p.m.
YQR
-
ORD
8h 01m1 stop
United Airlines Logo
1:55 p.m. - 10:51 p.m.
ORD
-
YQR
8h 56m1 stop
C$ 497United Airlines
Thu, 5 Feb - Mon, 9 Feb
Multiple Airlines Logo
7:00 a.m. - 2:17 p.m.
YQR
-
ORD
31h 17m3 stops
Multiple Airlines Logo
2:20 p.m. - 10:32 a.m.
ORD
-
YQR
20h 12m2 stops
C$ 561Multiple Airlines
Thu, 5 Feb - Mon, 9 Feb
United Airlines Logo
5:40 a.m. - 8:17 p.m.
YQR
-
ORD
14h 37m2 stops
United Airlines Logo
1:55 p.m. - 10:51 p.m.
ORD
-
YQR
8h 56m1 stop
C$ 579United Airlines
Mon, 12 Jan - Thu, 15 Jan
Delta Logo
11:45 a.m. - 8:40 a.m.
YQR
-
ORD
20h 55m1 stop
Delta Logo
8:50 a.m. - 6:20 p.m.
ORD
-
YQR
9h 30m1 stop
C$ 617Delta
Mon, 12 Jan - Thu, 15 Jan
WestJet Logo
7:00 a.m. - 6:58 p.m.
YQR
-
ORD
11h 58m2 stops
WestJet Logo
7:10 a.m. - 1:15 a.m.
ORD
-
YQR
18h 05m2 stops
C$ 624WestJet
Sat, 10 Jan - Wed, 4 Mar

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
5 Feb
YQR4:25 p.m.Regina
21h 10m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
9 Feb
ORD2:20 p.m.Chicago O'Hare Intl
6h 46m
1 stop
YQR9:06 p.m.Regina
C$ 302
Find similar
WestJet
5 Feb
YQR7:05 a.m.Regina
30h 30m
2 stops
ORD1:35 p.m.Chicago O'Hare Intl
9 Feb
ORD2:20 p.m.Chicago O'Hare Intl
6h 46m
1 stop
YQR9:06 p.m.Regina
C$ 405
Find similar
WestJet
5 Feb
YQR6:10 p.m.Regina
19h 25m
2 stops
ORD1:35 p.m.Chicago O'Hare Intl
9 Feb
ORD2:20 p.m.Chicago O'Hare Intl
44h 12m
2 stops
YQR10:32 a.m.Regina
C$ 413
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
10 Jan
YQR10:45 a.m.Regina
13h 14m
1 stop
ORD11:59 p.m.Chicago O'Hare Intl
4 Mar
ORD7:10 a.m.Chicago O'Hare Intl
15h 41m
1 stop
YQR10:51 p.m.Regina
C$ 306
Find similar
United Airlines
10 Jan
YQR10:45 a.m.Regina
8h 01m
1 stop
ORD6:46 p.m.Chicago O'Hare Intl
4 Mar
ORD7:25 a.m.Chicago O'Hare Intl
15h 26m
2 stops
YQR10:51 p.m.Regina
C$ 478
Find similar
United Airlines
5 Feb
YQR10:45 a.m.Regina
8h 01m
1 stop
ORD6:46 p.m.Chicago O'Hare Intl
9 Feb
ORD1:55 p.m.Chicago O'Hare Intl
8h 56m
1 stop
YQR10:51 p.m.Regina
C$ 497
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 18 December 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 5/2

4:25 p.m.-1:35 p.m.

1 stop21h 10m

Chicago O'Hare Intl

Mon 9/2

2:20 p.m.-9:06 p.m.

1 stop6h 46m

C$ 302

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 10/1

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

1 stop13h 14m

Chicago O'Hare Intl

Wed 4/3

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

1 stop15h 41m

C$ 306

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/2

7:05 a.m.-1:35 p.m.

2 stops30h 30m

Chicago O'Hare Intl

Mon 9/2

2:20 p.m.-9:06 p.m.

1 stop6h 46m

C$ 405

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/2

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

2 stops19h 25m

Chicago O'Hare Intl

Mon 9/2

2:20 p.m.-10:32 a.m.

2 stops44h 12m

C$ 413

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 10/1

10:45 a.m.-6:46 p.m.

1 stop8h 01m

Chicago O'Hare Intl

Wed 4/3

7:25 a.m.-10:51 p.m.

2 stops15h 26m

C$ 478

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/2

10:45 a.m.-6:46 p.m.

1 stop8h 01m

Chicago O'Hare Intl

Mon 9/2

1:55 p.m.-10:51 p.m.

1 stop8h 56m

C$ 497

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/2

7:00 a.m.-2:17 p.m.

3 stops31h 17m

Chicago O'Hare Intl

Mon 9/2

2:20 p.m.-10:32 a.m.

2 stops20h 12m

C$ 561

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 12/1

5:40 a.m.-8:17 p.m.

2 stops14h 37m

Chicago O'Hare Intl

Thu 15/1

1:55 p.m.-10:51 p.m.

1 stop8h 56m

C$ 579

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 12/1

11:45 a.m.-8:40 a.m.

1 stop20h 55m

Chicago O'Hare Intl

Thu 15/1

8:50 a.m.-6:20 p.m.

1 stop9h 30m

C$ 617

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 10/1

7:00 a.m.-6:58 p.m.

2 stops11h 58m

Chicago O'Hare Intl

Wed 4/3

7:10 a.m.-1:15 a.m.

2 stops18h 05m

C$ 624

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 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$ 504. 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$ 805.

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$ 461. 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$ 667 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

Fastest flight time

10h 41m

Direct flights

None
The fastest flight from Regina to Chicago O'Hare Intl Airport takes 10h 41m
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 10h 41m 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$ 405Free CancellationRating
7.1
10,534 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
Skokie
Hammond
Harvey
Naperville
Glenview
Great Lakes
Wheeling
Elmhurst
Harvard
Merrillville
Elk Grove Village
Oak Brook
Kenosha

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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