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Cheap flights from Regina to Chicago from C$ 235

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 11/5. 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

Find the cheapest flights from Regina to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
9:45 a.m. - 9:39 p.m.
YQR
-
ORD
10h 54m
1 stop
United Airlines Logo
6:00 a.m. - 9:30 p.m.
ORD
-
YQR
16h 30m
1 stop
C$ 452United Airlines
Tue, 2 Jun - Sat, 6 Jun
United Airlines Logo
9:45 a.m. - 9:39 p.m.
YQR
-
ORD
10h 54m
1 stop
United Airlines Logo
6:00 a.m. - 9:30 p.m.
ORD
-
YQR
16h 30m
1 stop
C$ 453United Airlines
Tue, 2 Jun - Sat, 6 Jun
United Airlines Logo
9:45 a.m. - 12:44 a.m.
YQR
-
ORD
13h 59m
1 stop
United Airlines Logo
6:00 a.m. - 9:30 p.m.
ORD
-
YQR
16h 30m
1 stop
C$ 455United Airlines
Wed, 10 Jun - Sat, 13 Jun
Delta Logo
10:45 a.m. - 9:20 p.m.
YQR
-
ORD
9h 35m
1 stop
Delta Logo
8:42 a.m. - 5:20 p.m.
ORD
-
YQR
9h 38m
1 stop
C$ 479Delta
Thu, 14 May - Sun, 17 May
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
Multiple Airlines Logo
8:06 p.m. - 5:20 p.m.
ORD
-
YQR
22h 14m
1 stop
C$ 482Multiple Airlines
Mon, 25 May - Mon, 1 Jun
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$ 505Delta
Mon, 25 May - Mon, 1 Jun
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
9:20 p.m. - 9:02 a.m.
ORD
-
YQR
12h 42m
1 stop
C$ 511Air Canada
Thu, 21 May - Mon, 25 May
Delta Logo
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
Delta Logo
8:36 a.m. - 5:20 p.m.
ORD
-
YQR
9h 44m
1 stop
C$ 522Delta
Fri, 5 Jun - Sun, 7 Jun
Delta Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
Delta Logo
8:36 a.m. - 5:20 p.m.
ORD
-
YQR
9h 44m
1 stop
C$ 523Delta
Fri, 5 Jun - Sun, 7 Jun
Multiple Airlines Logo
11:50 a.m. - 9:45 a.m.
YQR
-
MDW
20h 55m
2 stops
Multiple Airlines Logo
10:15 a.m. - 12:35 a.m.
MDW
-
YQR
15h 20m
1 stop
C$ 738Multiple Airlines
Mon, 25 May - Mon, 1 Jun

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Delta flights from Regina to Chicago

Our best Delta deals on Regina to Chicago flight tickets
Delta
14 May
YQR10:45 a.m.Regina
9h 35m
1 stop
ORD9:20 p.m.Chicago O'Hare Intl
17 May
ORD8:42 a.m.Chicago O'Hare Intl
9h 38m
1 stop
YQR5:20 p.m.Regina
C$ 479
Delta
25 May
YQR10:45 a.m.Regina
6h 11m
1 stop
MDW5:56 p.m.Chicago Midway
1 Jun
MDW9:23 a.m.Chicago Midway
8h 57m
1 stop
YQR5:20 p.m.Regina
C$ 505
Delta
5 Jun
YQR8:35 a.m.Regina
7h 05m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
7 Jun
ORD8:36 a.m.Chicago O'Hare Intl
9h 44m
1 stop
YQR5:20 p.m.Regina
C$ 522

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets
WestJet
5 Jun
YQR8:35 a.m.Regina
7h 05m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
7 Jun
ORD5:30 p.m.Chicago O'Hare Intl
18h 45m
2 stops
YQR11:15 a.m.Regina
C$ 688
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
27h 15m
2 stops
YQR7:45 p.m.Regina
C$ 713
WestJet
21 May
YQR8:20 p.m.Regina
19h 20m
2 stops
ORD4:40 p.m.Chicago O'Hare Intl
25 May
ORD5:30 p.m.Chicago O'Hare Intl
18h 45m
2 stops
YQR11:15 a.m.Regina
C$ 787

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 29 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

Tue 2/6

9:45 a.m.-9:39 p.m.

1 stop10h 54m

Chicago O'Hare Intl

Sat 6/6

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

1 stop16h 30m

C$ 452

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 2/6

9:45 a.m.-9:39 p.m.

1 stop10h 54m

Chicago O'Hare Intl

Sat 6/6

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

1 stop16h 30m

C$ 453

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 10/6

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

1 stop13h 59m

Chicago O'Hare Intl

Sat 13/6

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

1 stop16h 30m

C$ 455

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 14/5

10:45 a.m.-9:20 p.m.

1 stop9h 35m

Chicago O'Hare Intl

Sun 17/5

8:42 a.m.-5:20 p.m.

1 stop9h 38m

C$ 479

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 25/5

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

1 stop8h 40m

Chicago O'Hare Intl

Mon 1/6

8:06 p.m.-5:20 p.m.

1 stop22h 14m

C$ 482
Quickest round-trip

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 25/5

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

1 stop6h 11m

Chicago Midway

Mon 1/6

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

1 stop8h 57m

C$ 505

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 21/5

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

1 stop8h 10m

Chicago O'Hare Intl

Mon 25/5

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

1 stop12h 42m

C$ 511

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 5/6

8:35 a.m.-4:40 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Sun 7/6

8:36 a.m.-5:20 p.m.

1 stop9h 44m

C$ 522

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

8:36 a.m.-5:20 p.m.

1 stop9h 44m

C$ 523

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 25/5

11:50 a.m.-9:45 a.m.

2 stops20h 55m

Chicago Midway

Mon 1/6

10:15 a.m.-12:35 a.m.

1 stop15h 20m

C$ 738

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 May is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 219.

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 20m

Direct flights

None
The fastest flight from Regina to Chicago takes 6h 20m
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 20m.

  • 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