Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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 9/3. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Regina to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
6:55 a.m. - 4:43 p.m.
YQR
-
ORD
8h 48m
1 stop
WestJet Logo
5:30 p.m. - 1:07 a.m.
ORD
-
YQR
8h 37m
1 stop
C$ 322WestJet
Fri, 29 May - Tue, 2 Jun
WestJet Logo
8:35 a.m. - 4:43 p.m.
YQR
-
ORD
7h 08m
1 stop
WestJet Logo
5:30 p.m. - 11:02 p.m.
ORD
-
YQR
6h 32m
1 stop
C$ 351WestJet
Thu, 30 Apr - Mon, 4 May
WestJet Logo
8:35 a.m. - 4:43 p.m.
YQR
-
ORD
7h 08m
1 stop
WestJet Logo
5:30 p.m. - 4:55 p.m.
ORD
-
YQR
24h 25m
2 stops
C$ 387WestJet
Thu, 30 Apr - Mon, 4 May
WestJet Logo
6:55 a.m. - 4:43 p.m.
YQR
-
ORD
8h 48m
1 stop
WestJet Logo
5:30 p.m. - 11:02 p.m.
ORD
-
YQR
6h 32m
1 stop
C$ 388WestJet
Wed, 17 Jun - Mon, 22 Jun
WestJet Logo
5:30 p.m. - 4:43 p.m.
YQR
-
ORD
22h 13m
2 stops
WestJet Logo
5:30 p.m. - 4:55 p.m.
ORD
-
YQR
24h 25m
2 stops
C$ 393WestJet
Fri, 29 May - Tue, 2 Jun
United Airlines Logo
9:45 a.m. - 12:30 a.m.
YQR
-
ORD
13h 45m
1 stop
United Airlines Logo
12:55 p.m. - 9:30 p.m.
ORD
-
YQR
9h 35m
1 stop
C$ 400United Airlines
Sun, 12 Apr - Wed, 15 Apr
Multiple Airlines Logo
6:55 a.m. - 7:06 p.m.
YQR
-
ORD
11h 11m
2 stops
Multiple Airlines Logo
5:30 p.m. - 11:02 p.m.
ORD
-
YQR
6h 32m
1 stop
C$ 413Multiple Airlines
Mon, 4 May - Fri, 8 May
Air Canada Logo
5:00 a.m. - 1:01 p.m.
YQR
-
ORD
8h 01m
1 stop
Air Canada Logo
8:40 p.m. - 10:39 a.m.
ORD
-
YQR
13h 59m
1 stop
C$ 466Air Canada
Mon, 2 Mar - Tue, 3 Mar
Delta Logo
11:40 a.m. - 6:40 p.m.
YQR
-
MDW
7h 00m
1 stop
Delta Logo
7:20 p.m. - 6:31 p.m.
MDW
-
YQR
23h 11m
1 stop
C$ 545Delta
Mon, 2 Mar - Tue, 3 Mar
Delta Logo
11:40 a.m. - 6:40 p.m.
YQR
-
MDW
7h 00m
1 stop
Delta Logo
7:20 p.m. - 6:31 p.m.
MDW
-
YQR
23h 11m
1 stop
C$ 546Delta
Mon, 2 Mar - Tue, 3 Mar

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets
WestJet
29 May
YQR6:55 a.m.Regina
8h 48m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
2 Jun
ORD5:30 p.m.Chicago O'Hare Intl
8h 37m
1 stop
YQR1:07 a.m.Regina
C$ 322
WestJet
30 Apr
YQR8:35 a.m.Regina
7h 08m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
4 May
ORD5:30 p.m.Chicago O'Hare Intl
6h 32m
1 stop
YQR11:02 p.m.Regina
C$ 351
WestJet
30 Apr
YQR8:35 a.m.Regina
7h 08m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
4 May
ORD5:30 p.m.Chicago O'Hare Intl
24h 25m
2 stops
YQR4:55 p.m.Regina
C$ 387

United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets
United Airlines
12 Apr
YQR9:45 a.m.Regina
13h 45m
1 stop
ORD12:30 a.m.Chicago O'Hare Intl
15 Apr
ORD12:55 p.m.Chicago O'Hare Intl
9h 35m
1 stop
YQR9:30 p.m.Regina
C$ 400
United Airlines
13 Feb
YQR10:45 a.m.Regina
24h 34m
1 stop
ORD11:19 a.m.Chicago O'Hare Intl
17 Feb
ORD12:50 p.m.Chicago O'Hare Intl
10h 01m
1 stop
YQR10:51 p.m.Regina
C$ 984

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 24 January 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

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 29/5

6:55 a.m.-4:43 p.m.

1 stop8h 48m

Chicago O'Hare Intl

Tue 2/6

5:30 p.m.-1:07 a.m.

1 stop8h 37m

C$ 322

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 30/4

8:35 a.m.-4:43 p.m.

1 stop7h 08m

Chicago O'Hare Intl

Mon 4/5

5:30 p.m.-11:02 p.m.

1 stop6h 32m

C$ 351

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 30/4

8:35 a.m.-4:43 p.m.

1 stop7h 08m

Chicago O'Hare Intl

Mon 4/5

5:30 p.m.-4:55 p.m.

2 stops24h 25m

C$ 387

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 17/6

6:55 a.m.-4:43 p.m.

1 stop8h 48m

Chicago O'Hare Intl

Mon 22/6

5:30 p.m.-11:02 p.m.

1 stop6h 32m

C$ 388

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 29/5

5:30 p.m.-4:43 p.m.

2 stops22h 13m

Chicago O'Hare Intl

Tue 2/6

5:30 p.m.-4:55 p.m.

2 stops24h 25m

C$ 393

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 12/4

9:45 a.m.-12:30 a.m.

1 stop13h 45m

Chicago O'Hare Intl

Wed 15/4

12:55 p.m.-9:30 p.m.

1 stop9h 35m

C$ 400

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 4/5

6:55 a.m.-7:06 p.m.

2 stops11h 11m

Chicago O'Hare Intl

Fri 8/5

5:30 p.m.-11:02 p.m.

1 stop6h 32m

C$ 413

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 2/3

5:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago O'Hare Intl

Tue 3/3

8:40 p.m.-10:39 a.m.

1 stop13h 59m

C$ 466

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 2/3

11:40 a.m.-6:40 p.m.

1 stop7h 00m

Chicago Midway

Tue 3/3

7:20 p.m.-6:31 p.m.

1 stop23h 11m

C$ 545

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 2/3

11:40 a.m.-6:40 p.m.

1 stop7h 00m

Chicago Midway

Tue 3/3

7:20 p.m.-6:31 p.m.

1 stop23h 11m

C$ 546

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

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 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$ 381.

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

7h 00m

Direct flights

None
The fastest flight from Regina to Chicago takes 7h 00m
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 7h 00m.

  • 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
Air CanadaPriceFrom C$ 177Free CancellationRating
7.1
10,652 reviews
Search Air Canada flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 23/2
Mon 2/3
By creating a price alert you accept our terms of use and privacy policy.

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