Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Saskatchewan to Chicago from C$ 164

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Saskatchewan to Chicago departing on 27/5. 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

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 Saskatchewan 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. - 11:15 a.m.
ORD
-
YQR
18h 45m
2 stops
C$ 369WestJet
Sat, 30 May - Wed, 3 Jun
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 3:40 p.m.
ORD
-
YQR
23h 10m
1 stop
C$ 379WestJet
Sat, 30 May - Wed, 3 Jun
Air Canada Logo
5:00 a.m. - 1:05 p.m.
YXE
-
ORD
7h 05m
1 stop
Air Canada Logo
7:55 a.m. - 1:31 p.m.
ORD
-
YXE
6h 36m
1 stop
C$ 407Air Canada
Tue, 14 Apr - Sat, 18 Apr
United Airlines Logo
9:45 a.m. - 12:30 a.m.
YQR
-
ORD
13h 45m
1 stop
United Airlines Logo
7:00 a.m. - 9:30 p.m.
ORD
-
YQR
15h 30m
1 stop
C$ 418United Airlines
Thu, 23 Apr - Fri, 24 Apr
Multiple Airlines Logo
3:25 p.m. - 6:47 a.m.
YQR
-
ORD
14h 22m
2 stops
Multiple Airlines Logo
2:20 p.m. - 10:44 a.m.
ORD
-
YQR
21h 24m
1 stop
C$ 429Multiple Airlines
Thu, 23 Apr - Fri, 24 Apr
Air Canada Logo
5:00 a.m. - 1:05 p.m.
YXE
-
ORD
7h 05m
1 stop
Air Canada Logo
7:55 a.m. - 1:31 p.m.
ORD
-
YXE
6h 36m
1 stop
C$ 433Air Canada
Tue, 14 Apr - Sat, 18 Apr
United Airlines Logo
5:00 a.m. - 1:05 p.m.
YQR
-
ORD
7h 05m
1 stop
United Airlines Logo
2:35 p.m. - 9:30 p.m.
ORD
-
YQR
7h 55m
1 stop
C$ 499United Airlines
Sun, 29 Mar - Thu, 2 Apr
Delta Logo
7:10 a.m. - 1:32 p.m.
YXE
-
MDW
5h 22m
1 stop
Delta Logo
2:12 p.m. - 12:48 a.m.
MDW
-
YXE
11h 36m
2 stops
C$ 506Delta
Tue, 14 Apr - Sat, 18 Apr
Delta Logo
7:10 a.m. - 8:17 p.m.
YXE
-
ORD
12h 07m
2 stops
Delta Logo
6:15 a.m. - 1:37 p.m.
ORD
-
YXE
8h 22m
1 stop
C$ 506Delta
Tue, 24 Mar - Tue, 31 Mar
Multiple Airlines Logo
9:45 p.m. - 2:20 p.m.
YQR
-
MDW
16h 35m
2 stops
Multiple Airlines Logo
12:45 p.m. - 12:15 a.m.
MDW
-
YQR
12h 30m
1 stop
C$ 514Multiple Airlines
Sat, 7 Mar - Sat, 14 Mar

WestJet flights from Saskatchewan to Chicago

Our best WestJet deals on Saskatchewan to Chicago flight tickets
WestJet
27 Feb
YQR6:10 a.m.Regina
7h 25m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
30 Apr
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
C$ 384
WestJet
24 Apr
YQR5:10 a.m.Regina
7h 25m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
26 Apr
ORD5:30 p.m.Chicago O'Hare Intl
18h 20m
1 stop
YQR10:50 a.m.Regina
C$ 394
WestJet
24 Apr
YQR5:10 a.m.Regina
7h 25m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
26 Apr
ORD5:30 p.m.Chicago O'Hare Intl
18h 45m
2 stops
YQR11:15 a.m.Regina
C$ 396

United Airlines flights from Saskatchewan to Chicago

Our best United Airlines deals on Saskatchewan to Chicago flight tickets
United Airlines
29 Mar
YQR5:00 a.m.Regina
7h 05m
1 stop
ORD1:05 p.m.Chicago O'Hare Intl
2 Apr
ORD2:35 p.m.Chicago O'Hare Intl
7h 55m
1 stop
YQR9:30 p.m.Regina
C$ 499
United Airlines
23 Mar
YQR9:45 a.m.Regina
10h 44m
1 stop
ORD9:29 p.m.Chicago O'Hare Intl
27 Mar
ORD8:40 p.m.Chicago O'Hare Intl
13h 59m
1 stop
YQR9:39 a.m.Regina
C$ 558
United Airlines
25 Mar
YQR9:45 a.m.Regina
12h 10m
1 stop
ORD10:55 p.m.Chicago O'Hare Intl
1 Apr
ORD8:45 a.m.Chicago O'Hare Intl
14h 32m
2 stops
YQR10:17 p.m.Regina
C$ 573

momondo Fare Finder

 
Customize your flight search to find flights from Saskatchewan 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 9 February 2026.
Use the filters below to find and compare flights from Saskatchewan to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 30/5

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

1 stop8h 40m

Chicago O'Hare Intl

Wed 3/6

5:30 p.m.-11:15 a.m.

2 stops18h 45m

C$ 369

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 30/5

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

1 stop8h 40m

Chicago O'Hare Intl

Wed 3/6

5:30 p.m.-3:40 p.m.

1 stop23h 10m

C$ 379

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 14/4

5:00 a.m.-1:05 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Sat 18/4

7:55 a.m.-1:31 p.m.

1 stop6h 36m

C$ 407

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 23/4

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

1 stop13h 45m

Chicago O'Hare Intl

Fri 24/4

7:00 a.m.-9:30 p.m.

1 stop15h 30m

C$ 418

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 23/4

3:25 p.m.-6:47 a.m.

2 stops14h 22m

Chicago O'Hare Intl

Fri 24/4

2:20 p.m.-10:44 a.m.

1 stop21h 24m

C$ 429

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 14/4

5:00 a.m.-1:05 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Sat 18/4

7:55 a.m.-1:31 p.m.

1 stop6h 36m

C$ 433

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 29/3

5:00 a.m.-1:05 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Thu 2/4

2:35 p.m.-9:30 p.m.

1 stop7h 55m

C$ 499

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Tue 14/4

7:10 a.m.-1:32 p.m.

1 stop5h 22m

Chicago Midway

Sat 18/4

2:12 p.m.-12:48 a.m.

2 stops11h 36m

C$ 506

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 24/3

7:10 a.m.-8:17 p.m.

2 stops12h 07m

Chicago O'Hare Intl

Tue 31/3

6:15 a.m.-1:37 p.m.

1 stop8h 22m

C$ 506

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 7/3

9:45 p.m.-2:20 p.m.

2 stops16h 35m

Chicago Midway

Sat 14/3

12:45 p.m.-12:15 a.m.

1 stop12h 30m

C$ 514

Flights are sorted by cheapest round-trip flights first.

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Saskatchewan 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

Can stopping save me money on Saskatchewan to Chicago flights?

You could potentially save up to 23% on your flight if you consider stops on a Saskatchewan to Chicago flight.

Cheap Saskatchewan to Chicago flight deals and tips

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

Fastest flight time

5h 15m

Direct flights

None
The fastest flight from Saskatchewan to Chicago takes 5h 15m
There are no direct flights from Saskatchewan to Chicago. There are no popular flight routes from Saskatchewan to Chicago.
Search flight deals

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

    Prices for flights from Saskatchewan to Chicago were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Saskatchewan to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Saskatchewan to Chicago

Compare and see reviews for airlines that fly from Saskatchewan to Chicago with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 173Free CancellationRating
7.2
3,256 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 175Free CancellationRating
7.1
10,698 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 Saskatchewan to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Saskatchewan to Chicago. momondo saves you time and could save you money on your trip.

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

Flights from Saskatchewan to Chicago 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 Saskatchewan to Chicago?

Once all potential Saskatchewan 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 Saskatchewan to Chicago right now. Can momondo alert me if prices change?

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

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
Wed 11/3
Wed 18/3
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