Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Regina from $196

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Regina departing on 6/18. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? 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 Chicago to Regina

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:25 pm - 5:20 pm
ORD
-
YQR
23h 55m
1 stop
Multiple Airlines Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$398Multiple Airlines
Fri, Jun 5 - Mon, Jun 8
WestJet Logo
5:30 pm - 1:10 am
ORD
-
YQR
8h 40m
1 stop
WestJet Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$424WestJet
Tue, Aug 18 - Tue, Aug 25
Multiple Airlines Logo
6:31 pm - 5:20 pm
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
10:45 am - 5:24 pm
YQR
-
ORD
5h 39m
1 stop
$428Multiple Airlines
Mon, Jun 22 - Mon, Jun 29
Multiple Airlines Logo
6:39 pm - 5:20 pm
ORD
-
YQR
23h 41m
1 stop
Multiple Airlines Logo
6:00 am - 12:49 am
YQR
-
ORD
17h 49m
2 stops
$456Multiple Airlines
Wed, Jul 15 - Wed, Jul 22
United Airlines Logo
2:33 pm - 9:30 pm
ORD
-
YQR
7h 57m
1 stop
United Airlines Logo
9:45 am - 10:49 pm
YQR
-
ORD
12h 04m
1 stop
$468United Airlines
Sat, Jun 6 - Mon, Jun 8
Air Canada Logo
8:40 pm - 9:05 am
ORD
-
YQR
13h 25m
1 stop
Air Canada Logo
5:45 am - 2:55 pm
YQR
-
ORD
8h 10m
1 stop
$471Air Canada
Fri, Jun 19 - Sun, Jun 21
United Airlines Logo
6:00 am - 9:30 pm
ORD
-
YQR
16h 30m
1 stop
United Airlines Logo
9:45 am - 11:19 pm
YQR
-
ORD
12h 34m
1 stop
$487United Airlines
Tue, Jun 23 - Mon, Jun 29
Air Canada Logo
8:45 am - 7:05 pm
ORD
-
YQR
11h 20m
2 stops
Air Canada Logo
5:45 am - 2:55 pm
YQR
-
ORD
8h 10m
1 stop
$489Air Canada
Tue, Oct 20 - Sat, Oct 24
Multiple Airlines Logo
9:37 pm - 5:20 pm
ORD
-
YQR
20h 43m
2 stops
Multiple Airlines Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$491Multiple Airlines
Fri, Jun 5 - Mon, Jun 8
Multiple Airlines Logo
6:31 pm - 5:20 pm
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
10:45 am - 8:03 am
YQR
-
ORD
44h 18m
2 stops
$497Multiple Airlines
Mon, Jun 22 - Mon, Jun 29

United Airlines flights from Chicago to Regina

Our best United Airlines deals on Chicago to Regina flight tickets
United Airlines
Jun 6
ORD2:33 pmChicago O'Hare Intl
7h 57m
1 stop
YQR9:30 pmRegina
Jun 8
YQR9:45 amRegina
12h 04m
1 stop
ORD10:49 pmChicago O'Hare Intl
$468
United Airlines
Jun 23
ORD6:00 amChicago O'Hare Intl
16h 30m
1 stop
YQR9:30 pmRegina
Jun 29
YQR9:45 amRegina
12h 34m
1 stop
ORD11:19 pmChicago O'Hare Intl
$487
United Airlines
Aug 11
ORD6:00 amChicago O'Hare Intl
16h 30m
1 stop
YQR9:30 pmRegina
Aug 12
YQR9:45 amRegina
12h 01m
1 stop
ORD10:46 pmChicago O'Hare Intl
$530

Delta flights from Chicago to Regina

Our best Delta deals on Chicago to Regina flight tickets
Delta
Jun 19
ORD12:27 pmChicago O'Hare Intl
5h 53m
1 stop
YQR5:20 pmRegina
Jun 21
YQR10:45 amRegina
8h 46m
2 stops
ORD8:31 pmChicago O'Hare Intl
$557
Delta
Jun 5
ORD7:07 amChicago O'Hare Intl
11h 13m
2 stops
YQR5:20 pmRegina
Jun 8
YQR10:45 amRegina
8h 46m
2 stops
ORD8:31 pmChicago O'Hare Intl
$562
Delta
Oct 13
ORD12:15 pmChicago O'Hare Intl
6h 05m
1 stop
YQR5:20 pmRegina
Oct 20
YQR6:00 amRegina
11h 40m
2 stops
ORD6:40 pmChicago O'Hare Intl
$563

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Regina 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 832,500 searches. Data last updated May 16, 2026.
Use the filters below to find and compare flights from Chicago to Regina that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/5

6:25 pm-5:20 pm

1 stop23h 55m

Regina

Mon 6/8

8:35 am-4:40 pm

1 stop7h 05m

$398
Quickest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 8/18

5:30 pm-1:10 am

1 stop8h 40m

Regina

Tue 8/25

8:35 am-4:40 pm

1 stop7h 05m

$424

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 6/22

6:31 pm-5:20 pm

1 stop23h 49m

Regina

Mon 6/29

10:45 am-5:24 pm

1 stop5h 39m

$428

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 7/15

6:39 pm-5:20 pm

1 stop23h 41m

Regina

Wed 7/22

6:00 am-12:49 am

2 stops17h 49m

$456

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 6/6

2:33 pm-9:30 pm

1 stop7h 57m

Regina

Mon 6/8

9:45 am-10:49 pm

1 stop12h 04m

$468

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

8:40 pm-9:05 am

1 stop13h 25m

Regina

Sun 6/21

5:45 am-2:55 pm

1 stop8h 10m

$471

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 6/23

6:00 am-9:30 pm

1 stop16h 30m

Regina

Mon 6/29

9:45 am-11:19 pm

1 stop12h 34m

$487

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 10/20

8:45 am-7:05 pm

2 stops11h 20m

Regina

Sat 10/24

5:45 am-2:55 pm

1 stop8h 10m

$489

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/5

9:37 pm-5:20 pm

2 stops20h 43m

Regina

Mon 6/8

8:35 am-4:40 pm

1 stop7h 05m

$491

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 6/22

6:31 pm-5:20 pm

1 stop23h 49m

Regina

Mon 6/29

10:45 am-8:03 am

2 stops44h 18m

$497

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Regina from

How to get the cheapest flight ticket from Chicago to Regina

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 Regina?

The month of November is another great option to travel to Regina, with average flight prices from Chicago averaging around $137.

When to book flights from Chicago to Regina

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Regina according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Regina (CHI to YQR) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Regina

Fastest flight time

5h 53m

Direct flights

None
The fastest flight from Chicago to Regina takes 5h 53m
There are no direct flights from Chicago to Regina. There are no popular flight routes from Chicago to Regina.
Search flight deals

Frequently asked questions about flying from Chicago to Regina

  • How far is Chicago to Regina by plane?

    The straight-line distance from Chicago to Regina is 1001.4 mi. Typically, this will take 5h 53m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago to Regina Airport?

    Prices for flights from Chicago to Regina Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Regina Airport?

  • How old do you have to be to fly from Chicago to Regina Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Regina Airport.

  • What documentation or ID do you need to fly to Regina Airport?

    The necessary travel and health documents for your Regina Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Chicago to Regina

Compare and see reviews for airlines that fly from Chicago to Regina with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $303Free CancellationRating
7.4
9,727 reviews
Search United Airlines flights
WestJetPriceFrom $330Free CancellationRating
7.2
3,336 reviews
Search WestJet flights

Traveling to a place near Regina?

Book flights to Regina if you plan to visit one of these locations
Moose Jaw

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Regina?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Regina for you.

Can I find flights from Chicago to Regina with flexible booking policies on momondo?

Flights from Chicago to Regina with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Regina?

momondo helps you find the best flight between Chicago and Regina by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Regina right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Regina, momondo offers a useful price alert feature which will track prices for flights to Regina from Chicago and alert you when they change.

An easier way to manage your Regina 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 6/15
Mon 6/22
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Canada

Airports servicing Saskatchewan

Saskatoon Airport