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Cheap flights from Regina to Chicago from C$ 249

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 6/6. 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

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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.
Multiple Airlines Logo
5:10 a.m. - 1:35 p.m.
YQR
-
ORD
7h 25m
1 stop
Multiple Airlines Logo
7:20 a.m. - 6:21 p.m.
ORD
-
YQR
12h 01m
1 stop
C$ 474Multiple Airlines
Fri, 17 Apr - Sun, 19 Apr
Air Canada Logo
5:45 a.m. - 1:25 p.m.
YQR
-
ORD
6h 40m
1 stop
Air Canada Logo
8:20 p.m. - 9:02 a.m.
ORD
-
YQR
13h 42m
1 stop
C$ 504Air Canada
Tue, 5 May - Wed, 6 May
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
9:55 a.m. - 7:07 p.m.
ORD
-
YQR
10h 12m
1 stop
C$ 505Air Canada
Tue, 5 May - Wed, 6 May
Air Canada Logo
5:45 a.m. - 8:08 p.m.
YQR
-
ORD
13h 23m
2 stops
Air Canada Logo
8:20 p.m. - 9:02 a.m.
ORD
-
YQR
13h 42m
1 stop
C$ 508Air Canada
Tue, 5 May - Wed, 6 May
Air Canada Logo
5:45 a.m. - 8:08 p.m.
YQR
-
ORD
13h 23m
2 stops
Air Canada Logo
9:55 a.m. - 7:07 p.m.
ORD
-
YQR
10h 12m
1 stop
C$ 509Air Canada
Tue, 5 May - Wed, 6 May
Delta Logo
10:45 a.m. - 6:13 p.m.
YQR
-
ORD
6h 28m
1 stop
Delta Logo
7:00 a.m. - 5:20 p.m.
ORD
-
YQR
11h 20m
2 stops
C$ 527Delta
Tue, 28 Apr - Tue, 5 May
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$ 530WestJet
Fri, 5 Jun - Sun, 7 Jun
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$ 533WestJet
Fri, 5 Jun - Sun, 7 Jun
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$ 537WestJet
Fri, 5 Jun - Sun, 7 Jun
Delta Logo
7:00 a.m. - 8:14 p.m.
YQR
-
ORD
12h 14m
2 stops
Delta Logo
12:30 p.m. - 5:20 p.m.
ORD
-
YQR
5h 50m
1 stop
C$ 543Delta
Sat, 16 May - Sat, 23 May

Air Canada flights from Regina to Chicago

Our best Air Canada deals on Regina to Chicago flight tickets
Air Canada
9 May
YQR5:45 a.m.Regina
6h 40m
1 stop
ORD1:25 p.m.Chicago O'Hare Intl
12 May
ORD8:45 a.m.Chicago O'Hare Intl
11h 22m
2 stops
YQR7:07 p.m.Regina
C$ 465
Air Canada
9 May
YQR5:45 a.m.Regina
13h 23m
2 stops
ORD8:08 p.m.Chicago O'Hare Intl
12 May
ORD8:45 a.m.Chicago O'Hare Intl
11h 22m
2 stops
YQR7:07 p.m.Regina
C$ 469
Air Canada
18 May
YQR5:45 a.m.Regina
8h 05m
1 stop
ORD2:50 p.m.Chicago O'Hare Intl
25 May
ORD8:35 p.m.Chicago O'Hare Intl
13h 27m
1 stop
YQR9:02 a.m.Regina
C$ 477

Delta flights from Regina to Chicago

Our best Delta deals on Regina to Chicago flight tickets
Delta
28 Apr
YQR10:45 a.m.Regina
6h 28m
1 stop
ORD6:13 p.m.Chicago O'Hare Intl
5 May
ORD7:00 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR5:20 p.m.Regina
C$ 527
Delta
16 May
YQR7:00 a.m.Regina
12h 14m
2 stops
ORD8:14 p.m.Chicago O'Hare Intl
23 May
ORD12:30 p.m.Chicago O'Hare Intl
5h 50m
1 stop
YQR5:20 p.m.Regina
C$ 543
Delta
25 Apr
YQR10:40 a.m.Regina
6h 31m
1 stop
ORD6:11 p.m.Chicago O'Hare Intl
30 Apr
ORD1:36 p.m.Chicago O'Hare Intl
12h 34m
2 stops
YQR1:10 a.m.Regina
C$ 548

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 3 April 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

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 17/4

5:10 a.m.-1:35 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Sun 19/4

7:20 a.m.-6:21 p.m.

1 stop12h 01m

C$ 474

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 5/5

5:45 a.m.-1:25 p.m.

1 stop6h 40m

Chicago O'Hare Intl

Wed 6/5

8:20 p.m.-9:02 a.m.

1 stop13h 42m

C$ 504

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 5/5

5:45 a.m.-2:55 p.m.

1 stop8h 10m

Chicago O'Hare Intl

Wed 6/5

9:55 a.m.-7:07 p.m.

1 stop10h 12m

C$ 505

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 5/5

5:45 a.m.-8:08 p.m.

2 stops13h 23m

Chicago O'Hare Intl

Wed 6/5

8:20 p.m.-9:02 a.m.

1 stop13h 42m

C$ 508

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 5/5

5:45 a.m.-8:08 p.m.

2 stops13h 23m

Chicago O'Hare Intl

Wed 6/5

9:55 a.m.-7:07 p.m.

1 stop10h 12m

C$ 509

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 28/4

10:45 a.m.-6:13 p.m.

1 stop6h 28m

Chicago O'Hare Intl

Tue 5/5

7:00 a.m.-5:20 p.m.

2 stops11h 20m

C$ 527
Quickest round-trip

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 5/6

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

1 stop8h 40m

Chicago O'Hare Intl

Sun 7/6

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

1 stop8h 40m

C$ 530

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 5/6

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

1 stop8h 40m

Chicago O'Hare Intl

Sun 7/6

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

1 stop8h 40m

C$ 533

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 5/6

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

1 stop8h 40m

Chicago O'Hare Intl

Sun 7/6

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

1 stop8h 40m

C$ 537

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 16/5

7:00 a.m.-8:14 p.m.

2 stops12h 14m

Chicago O'Hare Intl

Sat 23/5

12:30 p.m.-5:20 p.m.

1 stop5h 50m

C$ 543

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?

What is the cheapest month to fly to Chicago?

The month of April is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 385.

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 40m

Direct flights

None
The fastest flight from Regina to Chicago takes 6h 40m
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 40m.

  • 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 many operators does momondo search for flights from Regina Airport to Chicago?

  • 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?

Best airlines flying from Regina to Chicago

Compare and see reviews for airlines that fly from Regina to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom C$ 313Free CancellationRating
7.4
9,538 reviews
Search United Airlines flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Munster

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