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Cheap flights from Regina to Chicago from C$ 228

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 9/6. 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

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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
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$ 397WestJet
Tue, 9 Jun - Fri, 12 Jun
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 7:45 p.m.
ORD
-
YQR
27h 15m
2 stops
C$ 451WestJet
Tue, 9 Jun - Fri, 12 Jun
WestJet Logo
11:50 a.m. - 4:40 p.m.
YQR
-
ORD
27h 50m
2 stops
WestJet Logo
5:30 p.m. - 10:50 a.m.
ORD
-
YQR
18h 20m
1 stop
C$ 489WestJet
Fri, 5 Jun - Sun, 7 Jun
United Airlines Logo
9:45 a.m. - 6:51 p.m.
YQR
-
ORD
8h 06m
1 stop
United Airlines Logo
6:00 a.m. - 9:30 p.m.
ORD
-
YQR
16h 30m
1 stop
C$ 498United Airlines
Tue, 9 Jun - Tue, 16 Jun
United Airlines Logo
9:45 a.m. - 12:44 a.m.
YQR
-
ORD
13h 59m
1 stop
United Airlines Logo
7:05 a.m. - 9:30 p.m.
ORD
-
YQR
15h 25m
1 stop
C$ 524United Airlines
Fri, 12 Jun - Sat, 20 Jun
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
Multiple Airlines Logo
9:48 p.m. - 5:20 p.m.
ORD
-
YQR
20h 32m
2 stops
C$ 531Multiple Airlines
Tue, 9 Jun - Tue, 16 Jun
Air Canada Logo
12:40 p.m. - 7:48 p.m.
YQR
-
ORD
6h 08m
1 stop
Air Canada Logo
8:45 a.m. - 7:05 p.m.
ORD
-
YQR
11h 20m
2 stops
C$ 549Air Canada
Wed, 16 Sep - Sat, 19 Sep
Delta Logo
10:45 a.m. - 6:18 p.m.
YQR
-
MDW
6h 33m
1 stop
Delta Logo
9:49 a.m. - 5:20 p.m.
MDW
-
YQR
8h 31m
1 stop
C$ 658Delta
Tue, 28 Jul - Sat, 1 Aug
Delta Logo
10:45 a.m. - 6:18 p.m.
YQR
-
MDW
6h 33m
1 stop
Delta Logo
9:49 a.m. - 5:20 p.m.
MDW
-
YQR
8h 31m
1 stop
C$ 660Delta
Thu, 9 Jul - Tue, 14 Jul
Multiple Airlines Logo
9:05 p.m. - 2:35 p.m.
YQR
-
MDW
16h 30m
2 stops
Multiple Airlines Logo
3:20 p.m. - 12:35 a.m.
MDW
-
YQR
10h 15m
1 stop
C$ 774Multiple Airlines
Sun, 21 Jun - Fri, 26 Jun

Air Canada flights from Regina to Chicago

Our best Air Canada deals on Regina to Chicago flight tickets
Air Canada
16 Sep
YQR12:40 p.m.Regina
6h 08m
1 stop
ORD7:48 p.m.Chicago O'Hare Intl
19 Sep
ORD8:45 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR7:05 p.m.Regina
C$ 549
Air Canada
16 Sep
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
19 Sep
ORD8:45 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR7:05 p.m.Regina
C$ 550
Air Canada
12 Sep
YQR12:40 p.m.Regina
6h 08m
1 stop
ORD7:48 p.m.Chicago O'Hare Intl
21 Sep
ORD8:40 p.m.Chicago O'Hare Intl
13h 30m
1 stop
YQR9:10 a.m.Regina
C$ 570

Delta flights from Regina to Chicago

Our best Delta deals on Regina to Chicago flight tickets
Delta
12 Jun
YQR10:45 a.m.Regina
7h 46m
1 stop
ORD7:31 p.m.Chicago O'Hare Intl
20 Jun
ORD7:01 a.m.Chicago O'Hare Intl
11h 19m
2 stops
YQR5:20 p.m.Regina
C$ 598
Delta
12 Jun
YQR10:45 a.m.Regina
5h 17m
1 stop
ORD5:02 p.m.Chicago O'Hare Intl
20 Jun
ORD7:01 a.m.Chicago O'Hare Intl
11h 19m
2 stops
YQR5:20 p.m.Regina
C$ 599
Delta
16 Sep
YQR7:00 a.m.Regina
12h 24m
2 stops
ORD8:24 p.m.Chicago O'Hare Intl
19 Sep
ORD8:55 a.m.Chicago O'Hare Intl
9h 25m
2 stops
YQR5:20 p.m.Regina
C$ 608

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 16 May 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

Tue 9/6

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

1 stop8h 40m

Chicago O'Hare Intl

Fri 12/6

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

1 stop8h 40m

C$ 397

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 9/6

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

1 stop8h 40m

Chicago O'Hare Intl

Fri 12/6

5:30 p.m.-7:45 p.m.

2 stops27h 15m

C$ 451

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 5/6

11:50 a.m.-4:40 p.m.

2 stops27h 50m

Chicago O'Hare Intl

Sun 7/6

5:30 p.m.-10:50 a.m.

1 stop18h 20m

C$ 489

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 9/6

9:45 a.m.-6:51 p.m.

1 stop8h 06m

Chicago O'Hare Intl

Tue 16/6

6:00 a.m.-9:30 p.m.

1 stop16h 30m

C$ 498

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 12/6

9:45 a.m.-12:44 a.m.

1 stop13h 59m

Chicago O'Hare Intl

Sat 20/6

7:05 a.m.-9:30 p.m.

1 stop15h 25m

C$ 524

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 9/6

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

1 stop8h 40m

Chicago O'Hare Intl

Tue 16/6

9:48 p.m.-5:20 p.m.

2 stops20h 32m

C$ 531

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 16/9

12:40 p.m.-7:48 p.m.

1 stop6h 08m

Chicago O'Hare Intl

Sat 19/9

8:45 a.m.-7:05 p.m.

2 stops11h 20m

C$ 549
Quickest round-trip

ReginaChicago

YQR - MDW

YQRMDW

Regina

Tue 28/7

10:45 a.m.-6:18 p.m.

1 stop6h 33m

Chicago Midway

Sat 1/8

9:49 a.m.-5:20 p.m.

1 stop8h 31m

C$ 658

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 9/7

10:45 a.m.-6:18 p.m.

1 stop6h 33m

Chicago Midway

Tue 14/7

9:49 a.m.-5:20 p.m.

1 stop8h 31m

C$ 660

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sun 21/6

9:05 p.m.-2:35 p.m.

2 stops16h 30m

Chicago Midway

Fri 26/6

3:20 p.m.-12:35 a.m.

1 stop10h 15m

C$ 774

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 October is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 278.

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 33m

Direct flights

None
The fastest flight from Regina to Chicago takes 6h 33m
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 33m.

  • 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