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Cheap flights from Regina to Chicago from C$ 234

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 23/4. 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.
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$ 385WestJet
Tue, 26 May - Fri, 29 May
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$ 394United Airlines
Tue, 26 May - Fri, 29 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$ 395WestJet
Tue, 26 May - Fri, 29 May
United Airlines Logo
9:45 a.m. - 12:44 a.m.
YQR
-
ORD
13h 59m
1 stop
United Airlines Logo
1:05 p.m. - 9:30 p.m.
ORD
-
YQR
9h 25m
1 stop
C$ 415United Airlines
Tue, 26 May - Fri, 29 May
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$ 424Air Canada
Mon, 1 Jun - Mon, 8 Jun
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
8:20 p.m. - 9:02 a.m.
ORD
-
YQR
13h 42m
1 stop
C$ 437Air Canada
Mon, 1 Jun - Mon, 8 Jun
Multiple Airlines Logo
7:15 a.m. - 5:00 p.m.
YQR
-
ORD
8h 45m
1 stop
Multiple Airlines Logo
5:30 p.m. - 11:20 p.m.
ORD
-
YQR
6h 50m
1 stop
C$ 443Multiple Airlines
Thu, 23 Apr - Thu, 14 May
Delta Logo
10:45 a.m. - 6:36 p.m.
YQR
-
MDW
6h 51m
1 stop
Delta Logo
9:29 a.m. - 5:20 p.m.
MDW
-
YQR
8h 51m
1 stop
C$ 483Delta
Mon, 27 Apr - Wed, 29 Apr
Delta Logo
10:40 a.m. - 6:40 p.m.
YQR
-
MDW
7h 00m
1 stop
Delta Logo
2:05 p.m. - 6:21 p.m.
MDW
-
YQR
5h 16m
1 stop
C$ 512Delta
Wed, 1 Apr - Wed, 8 Apr
Multiple Airlines Logo
6:00 a.m. - 9:40 a.m.
YQR
-
MDW
26h 40m
1 stop
Multiple Airlines Logo
3:20 p.m. - 12:50 p.m.
MDW
-
YQR
22h 30m
2 stops
C$ 651Multiple Airlines
Mon, 1 Jun - Mon, 8 Jun

Air Canada flights from Regina to Chicago

Our best Air Canada deals on Regina to Chicago flight tickets
Air Canada
1 Jun
YQR5:45 a.m.Regina
6h 40m
1 stop
ORD1:25 p.m.Chicago O'Hare Intl
8 Jun
ORD8:20 p.m.Chicago O'Hare Intl
13h 42m
1 stop
YQR9:02 a.m.Regina
C$ 424
Air Canada
1 Jun
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
8 Jun
ORD8:20 p.m.Chicago O'Hare Intl
13h 42m
1 stop
YQR9:02 a.m.Regina
C$ 436
Air Canada
30 Apr
YQR5:00 a.m.Regina
7h 05m
1 stop
ORD1:05 p.m.Chicago O'Hare Intl
4 May
ORD8:20 p.m.Chicago O'Hare Intl
13h 42m
1 stop
YQR9:02 a.m.Regina
C$ 454

United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets
United Airlines
26 May
YQR9:45 a.m.Regina
13h 59m
1 stop
ORD12:44 a.m.Chicago O'Hare Intl
29 May
ORD7:05 a.m.Chicago O'Hare Intl
15h 25m
1 stop
YQR9:30 p.m.Regina
C$ 394
United Airlines
26 May
YQR9:45 a.m.Regina
13h 59m
1 stop
ORD12:44 a.m.Chicago O'Hare Intl
29 May
ORD1:05 p.m.Chicago O'Hare Intl
9h 25m
1 stop
YQR9:30 p.m.Regina
C$ 415
United Airlines
26 May
YQR9:45 a.m.Regina
13h 59m
1 stop
ORD12:44 a.m.Chicago O'Hare Intl
29 May
ORD6:00 a.m.Chicago O'Hare Intl
16h 30m
1 stop
YQR9:30 p.m.Regina
C$ 434

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 March 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 26/5

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

1 stop8h 40m

Chicago O'Hare Intl

Fri 29/5

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

1 stop8h 40m

C$ 384

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 26/5

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

1 stop13h 59m

Chicago O'Hare Intl

Fri 29/5

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

1 stop15h 25m

C$ 394

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 26/5

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

1 stop8h 40m

Chicago O'Hare Intl

Fri 29/5

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

1 stop8h 40m

C$ 395

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 26/5

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

1 stop13h 59m

Chicago O'Hare Intl

Fri 29/5

1:05 p.m.-9:30 p.m.

1 stop9h 25m

C$ 415

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 1/6

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

1 stop6h 40m

Chicago O'Hare Intl

Mon 8/6

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

1 stop13h 42m

C$ 424

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 1/6

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

1 stop8h 10m

Chicago O'Hare Intl

Mon 8/6

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

1 stop13h 42m

C$ 436

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 23/4

7:15 a.m.-5:00 p.m.

1 stop8h 45m

Chicago O'Hare Intl

Thu 14/5

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

1 stop6h 50m

C$ 443

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 27/4

10:45 a.m.-6:36 p.m.

1 stop6h 51m

Chicago Midway

Wed 29/4

9:29 a.m.-5:20 p.m.

1 stop8h 51m

C$ 483
Quickest round-trip

ReginaChicago

YQR - MDW

YQRMDW

Regina

Wed 1/4

10:40 a.m.-6:40 p.m.

1 stop7h 00m

Chicago Midway

Wed 8/4

2:05 p.m.-6:21 p.m.

1 stop5h 16m

C$ 512

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 1/6

6:00 a.m.-9:40 a.m.

1 stop26h 40m

Chicago Midway

Mon 8/6

3:20 p.m.-12:50 p.m.

2 stops22h 30m

C$ 651

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$ 379.

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 05m

Direct flights

None
The fastest flight from Regina to Chicago takes 6h 05m
There are no direct flights from Regina to Chicago. There are no popular flight routes from Regina to Chicago.
Search flight deals

  • 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 05m.

  • 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$ 308Free CancellationRating
7.4
9,423 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
Munster
Hammond

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