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Cheap flights from Regina to Chicago from C$ 311

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 15/7. 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

Find the cheapest flights from Regina to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
5:45 a.m. - 1:23 p.m.
YQR
-
ORD
6h 38m
1 stop
United Airlines Logo
2:30 p.m. - 9:41 p.m.
ORD
-
YQR
8h 11m
1 stop
C$ 505United Airlines
Tue, 20 Oct - Sat, 24 Oct
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
8:45 a.m. - 7:05 p.m.
ORD
-
YQR
11h 20m
2 stops
C$ 520Air Canada
Tue, 20 Oct - Sat, 24 Oct
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
8:45 a.m. - 7:05 p.m.
ORD
-
YQR
11h 20m
2 stops
C$ 522Air Canada
Tue, 20 Oct - Sat, 24 Oct
Air Canada Logo
5:45 a.m. - 8:12 p.m.
YQR
-
ORD
13h 27m
2 stops
Air Canada Logo
8:45 a.m. - 7:05 p.m.
ORD
-
YQR
11h 20m
2 stops
C$ 525Air Canada
Tue, 20 Oct - Sat, 24 Oct
Air Canada Logo
5:45 a.m. - 8:12 p.m.
YQR
-
ORD
13h 27m
2 stops
Air Canada Logo
8:45 a.m. - 7:05 p.m.
ORD
-
YQR
11h 20m
2 stops
C$ 526Air Canada
Tue, 20 Oct - Sat, 24 Oct
Air Canada Logo
6:00 a.m. - 2:56 p.m.
YQR
-
ORD
8h 56m
1 stop
Air Canada Logo
6:30 p.m. - 10:39 a.m.
ORD
-
YQR
16h 09m
1 stop
C$ 543Air Canada
Sun, 22 Nov - Mon, 23 Nov
Multiple Airlines Logo
9:45 a.m. - 11:59 p.m.
YQR
-
ORD
13h 14m
1 stop
Multiple Airlines Logo
8:45 a.m. - 7:05 p.m.
ORD
-
YQR
11h 20m
2 stops
C$ 544Multiple Airlines
Sat, 19 Sep - Sat, 26 Sep
Delta Logo
12:45 p.m. - 7:34 p.m.
YQR
-
ORD
6h 49m
1 stop
Delta Logo
12:15 p.m. - 12:55 a.m.
ORD
-
YQR
12h 40m
2 stops
C$ 555Delta
Sun, 1 Nov - Tue, 19 Jan
Delta Logo
11:45 a.m. - 10:10 p.m.
YQR
-
MDW
9h 25m
2 stops
Delta Logo
9:30 a.m. - 7:21 p.m.
MDW
-
YQR
9h 51m
2 stops
C$ 555Delta
Sat, 31 Oct - Wed, 4 Nov
Multiple Airlines Logo
4:15 p.m. - 9:40 a.m.
YQR
-
MDW
16h 25m
2 stops
Multiple Airlines Logo
10:25 a.m. - 12:35 a.m.
MDW
-
YQR
15h 10m
1 stop
C$ 720Multiple Airlines
Wed, 8 Jul - Sat, 11 Jul

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Air Canada flights from Regina to Chicago

Our best Air Canada deals on Regina to Chicago flight tickets
Air Canada
20 Oct
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
24 Oct
ORD8:45 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR7:05 p.m.Regina
C$ 520
Air Canada
20 Oct
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
24 Oct
ORD8:45 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR7:05 p.m.Regina
C$ 522
Air Canada
20 Oct
YQR5:45 a.m.Regina
13h 27m
2 stops
ORD8:12 p.m.Chicago O'Hare Intl
24 Oct
ORD8:45 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR7:05 p.m.Regina
C$ 526

United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets
United Airlines
19 Sep
YQR9:45 a.m.Regina
9h 37m
1 stop
ORD8:22 p.m.Chicago O'Hare Intl
26 Sep
ORD2:30 p.m.Chicago O'Hare Intl
8h 11m
1 stop
YQR9:41 p.m.Regina
C$ 557
United Airlines
11 Sep
YQR9:45 a.m.Regina
12h 01m
1 stop
ORD10:46 p.m.Chicago O'Hare Intl
16 Sep
ORD1:30 p.m.Chicago O'Hare Intl
9h 00m
1 stop
YQR9:30 p.m.Regina
C$ 558
United Airlines
3 Jul
YQR9:45 a.m.Regina
13h 59m
1 stop
ORD12:44 a.m.Chicago O'Hare Intl
8 Jul
ORD6:00 a.m.Chicago O'Hare Intl
16h 30m
1 stop
YQR9:30 p.m.Regina
C$ 561

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 14 June 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
Quickest round-trip

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 20/10

5:45 a.m.-1:23 p.m.

1 stop6h 38m

Chicago O'Hare Intl

Sat 24/10

2:30 p.m.-9:41 p.m.

1 stop8h 11m

C$ 505

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 20/10

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

1 stop8h 10m

Chicago O'Hare Intl

Sat 24/10

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

2 stops11h 20m

C$ 520

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 20/10

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

1 stop8h 10m

Chicago O'Hare Intl

Sat 24/10

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

2 stops11h 20m

C$ 522

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 20/10

5:45 a.m.-8:12 p.m.

2 stops13h 27m

Chicago O'Hare Intl

Sat 24/10

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

2 stops11h 20m

C$ 524

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 20/10

5:45 a.m.-8:12 p.m.

2 stops13h 27m

Chicago O'Hare Intl

Sat 24/10

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

2 stops11h 20m

C$ 526

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 22/11

6:00 a.m.-2:56 p.m.

1 stop8h 56m

Chicago O'Hare Intl

Mon 23/11

6:30 p.m.-10:39 a.m.

1 stop16h 09m

C$ 543

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 19/9

9:45 a.m.-11:59 p.m.

1 stop13h 14m

Chicago O'Hare Intl

Sat 26/9

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

2 stops11h 20m

C$ 544

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 1/11

12:45 p.m.-7:34 p.m.

1 stop6h 49m

Chicago O'Hare Intl

Tue 19/1

12:15 p.m.-12:55 a.m.

2 stops12h 40m

C$ 555

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 31/10

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

2 stops9h 25m

Chicago Midway

Wed 4/11

9:30 a.m.-7:21 p.m.

2 stops9h 51m

C$ 555

ReginaChicago

YQR - MDW

YQRMDW

Regina

Wed 8/7

4:15 p.m.-9:40 a.m.

2 stops16h 25m

Chicago Midway

Sat 11/7

10:25 a.m.-12:35 a.m.

1 stop15h 10m

C$ 720

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$ 283.

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

5h 14m

Direct flights

None
The fastest flight from Regina to Chicago takes 5h 14m
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 5h 14m.

  • 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