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Cheap flights from Regina to Chicago from C$ 255

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 19/6. 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.
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
8:45 a.m. - 7:07 p.m.
ORD
-
YQR
11h 22m
2 stops
C$ 461Air Canada
Sat, 9 May - Tue, 12 May
Air Canada Logo
5:45 a.m. - 8:08 p.m.
YQR
-
ORD
13h 23m
2 stops
Air Canada Logo
8:45 a.m. - 7:07 p.m.
ORD
-
YQR
11h 22m
2 stops
C$ 465Air Canada
Sat, 9 May - Tue, 12 May
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
8:35 p.m. - 9:02 a.m.
ORD
-
YQR
13h 27m
1 stop
C$ 476Air Canada
Wed, 20 May - Wed, 27 May
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
8:45 a.m. - 7:07 p.m.
ORD
-
YQR
11h 22m
2 stops
C$ 483Air Canada
Sat, 9 May - Tue, 12 May
Air Canada Logo
5:45 a.m. - 8:08 p.m.
YQR
-
ORD
13h 23m
2 stops
Air Canada Logo
8:45 a.m. - 7:07 p.m.
ORD
-
YQR
11h 22m
2 stops
C$ 487Air Canada
Sat, 9 May - Tue, 12 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$ 504WestJet
Fri, 22 May - Sun, 24 May
WestJet Logo
8:20 p.m. - 4:40 p.m.
YQR
-
ORD
43h 20m
2 stops
WestJet Logo
5:30 p.m. - 11:20 p.m.
ORD
-
YQR
6h 50m
1 stop
C$ 521WestJet
Wed, 20 May - Wed, 27 May
Delta Logo
10:45 a.m. - 5:56 p.m.
YQR
-
MDW
6h 11m
1 stop
Delta Logo
9:23 a.m. - 5:20 p.m.
MDW
-
YQR
8h 57m
1 stop
C$ 540Delta
Sat, 9 May - Tue, 12 May
Delta Logo
10:45 a.m. - 5:56 p.m.
YQR
-
MDW
6h 11m
1 stop
Delta Logo
9:22 a.m. - 5:20 p.m.
MDW
-
YQR
8h 58m
2 stops
C$ 551Delta
Sat, 9 May - Tue, 12 May
Multiple Airlines Logo
10:45 a.m. - 5:56 p.m.
YQR
-
MDW
6h 11m
1 stop
Multiple Airlines Logo
6:00 a.m. - 5:20 p.m.
MDW
-
YQR
12h 20m
2 stops
C$ 982Multiple Airlines
Sat, 23 May - Sat, 30 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
8h 10m
1 stop
ORD2:55 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$ 461
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$ 465
Air Canada
20 May
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
27 May
ORD8:35 p.m.Chicago O'Hare Intl
13h 27m
1 stop
YQR9:02 a.m.Regina
C$ 476

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets
WestJet
22 May
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
24 May
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
C$ 504
WestJet
20 May
YQR8:20 p.m.Regina
43h 20m
2 stops
ORD4:40 p.m.Chicago O'Hare Intl
27 May
ORD5:30 p.m.Chicago O'Hare Intl
6h 50m
1 stop
YQR11:20 p.m.Regina
C$ 521
WestJet
5 Jun
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
7 Jun
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
C$ 537

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 9 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

Sat 9/5

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

1 stop8h 10m

Chicago O'Hare Intl

Tue 12/5

8:45 a.m.-7:07 p.m.

2 stops11h 22m

C$ 461

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 9/5

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

2 stops13h 23m

Chicago O'Hare Intl

Tue 12/5

8:45 a.m.-7:07 p.m.

2 stops11h 22m

C$ 465

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 20/5

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

1 stop8h 10m

Chicago O'Hare Intl

Wed 27/5

8:35 p.m.-9:02 a.m.

1 stop13h 27m

C$ 476

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 9/5

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

1 stop8h 10m

Chicago O'Hare Intl

Tue 12/5

8:45 a.m.-7:07 p.m.

2 stops11h 22m

C$ 483

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 9/5

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

2 stops13h 23m

Chicago O'Hare Intl

Tue 12/5

8:45 a.m.-7:07 p.m.

2 stops11h 22m

C$ 487

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 22/5

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

1 stop8h 40m

Chicago O'Hare Intl

Sun 24/5

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

1 stop8h 40m

C$ 504

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 20/5

8:20 p.m.-4:40 p.m.

2 stops43h 20m

Chicago O'Hare Intl

Wed 27/5

5:30 p.m.-11:20 p.m.

1 stop6h 50m

C$ 521
Quickest round-trip

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 9/5

10:45 a.m.-5:56 p.m.

1 stop6h 11m

Chicago Midway

Tue 12/5

9:23 a.m.-5:20 p.m.

1 stop8h 57m

C$ 540

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 9/5

10:45 a.m.-5:56 p.m.

1 stop6h 11m

Chicago Midway

Tue 12/5

9:22 a.m.-5:20 p.m.

2 stops8h 58m

C$ 551

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 23/5

10:45 a.m.-5:56 p.m.

1 stop6h 11m

Chicago Midway

Sat 30/5

6:00 a.m.-5:20 p.m.

2 stops12h 20m

C$ 982

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 January is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 386.

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 56m

Direct flights

None
The fastest flight from Regina to Chicago takes 6h 56m
There are no direct flights from Regina to Chicago. There are no popular flight routes from Regina to Chicago.
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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 56m.

  • 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 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?

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