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Cheap flights from Saskatchewan to Chicago from C$ 210

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 11/10. 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

Find the cheapest flights from Saskatchewan to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
8:50 a.m. - 4:40 p.m.
YXE
-
ORD
6h 50m
1 stop
WestJet Logo
5:30 p.m. - 11:10 p.m.
ORD
-
YXE
6h 40m
1 stop
C$ 475WestJet
Wed, 26 Aug - Mon, 31 Aug
WestJet Logo
7:00 a.m. - 4:40 p.m.
YXE
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 11:10 p.m.
ORD
-
YXE
6h 40m
1 stop
C$ 483WestJet
Fri, 18 Sep - Tue, 22 Sep
WestJet Logo
4:15 p.m. - 4:40 p.m.
YXE
-
ORD
23h 25m
2 stops
WestJet Logo
5:30 p.m. - 1:00 a.m.
ORD
-
YXE
8h 30m
1 stop
C$ 496WestJet
Tue, 18 Aug - Tue, 25 Aug
WestJet Logo
10:10 a.m. - 4:40 p.m.
YXE
-
ORD
29h 30m
2 stops
WestJet Logo
5:30 p.m. - 1:00 a.m.
ORD
-
YXE
8h 30m
1 stop
C$ 507WestJet
Tue, 25 Aug - Mon, 31 Aug
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$ 512WestJet
Wed, 2 Sep - Sat, 5 Sep
Air Canada Logo
7:50 p.m. - 9:00 a.m.
YXE
-
ORD
12h 10m
1 stop
Air Canada Logo
3:45 p.m. - 11:16 p.m.
ORD
-
YXE
8h 31m
1 stop
C$ 522Air Canada
Mon, 19 Oct - Wed, 21 Oct
Delta Logo
7:00 a.m. - 6:05 p.m.
YXE
-
MDW
10h 05m
2 stops
Delta Logo
12:28 p.m. - 1:00 a.m.
MDW
-
YXE
13h 32m
2 stops
C$ 523Delta
Tue, 20 Oct - Sat, 24 Oct
Delta Logo
6:00 a.m. - 6:25 p.m.
YXE
-
ORD
11h 25m
2 stops
Delta Logo
2:00 p.m. - 11:10 p.m.
ORD
-
YXE
10h 10m
2 stops
C$ 523Delta
Mon, 19 Oct - Wed, 21 Oct
United Airlines Logo
2:15 p.m. - 10:05 p.m.
YQR
-
ORD
6h 50m
1 stop
United Airlines Logo
5:55 a.m. - 9:30 p.m.
ORD
-
YQR
16h 35m
1 stop
C$ 597United Airlines
Mon, 7 Sep - Fri, 11 Sep
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$ 689United Airlines
Sun, 2 Aug - Sun, 9 Aug

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WestJet flights from Saskatchewan to Chicago

Our best WestJet deals on Saskatchewan to Chicago flight tickets
WestJet
26 Aug
YXE8:50 a.m.Saskatoon
6h 50m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
31 Aug
ORD5:30 p.m.Chicago O'Hare Intl
6h 40m
1 stop
YXE11:10 p.m.Saskatoon
C$ 475
WestJet
18 Sep
YXE7:00 a.m.Saskatoon
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
22 Sep
ORD5:30 p.m.Chicago O'Hare Intl
6h 40m
1 stop
YXE11:10 p.m.Saskatoon
C$ 483
WestJet
18 Aug
YXE4:15 p.m.Saskatoon
23h 25m
2 stops
ORD4:40 p.m.Chicago O'Hare Intl
25 Aug
ORD5:30 p.m.Chicago O'Hare Intl
8h 30m
1 stop
YXE1:00 a.m.Saskatoon
C$ 496

United Airlines flights from Saskatchewan to Chicago

Our best United Airlines deals on Saskatchewan to Chicago flight tickets
United Airlines
7 Sep
YQR2:15 p.m.Regina
6h 50m
1 stop
ORD10:05 p.m.Chicago O'Hare Intl
11 Sep
ORD5:55 a.m.Chicago O'Hare Intl
16h 35m
1 stop
YQR9:30 p.m.Regina
C$ 597
United Airlines
2 Aug
YQR9:45 a.m.Regina
13h 59m
1 stop
ORD12:44 a.m.Chicago O'Hare Intl
9 Aug
ORD6:00 a.m.Chicago O'Hare Intl
16h 30m
1 stop
YQR9:30 p.m.Regina
C$ 689
United Airlines
2 Aug
YQR9:45 a.m.Regina
13h 59m
1 stop
ORD12:44 a.m.Chicago O'Hare Intl
9 Aug
ORD7:09 a.m.Chicago O'Hare Intl
7h 11m
1 stop
YQR1:20 p.m.Regina
C$ 830

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 7 July 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

Cheapest round-trip
Quickest round-trip

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Wed 26/8

8:50 a.m.-4:40 p.m.

1 stop6h 50m

Chicago O'Hare Intl

Mon 31/8

5:30 p.m.-11:10 p.m.

1 stop6h 40m

C$ 475

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 18/9

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

1 stop8h 40m

Chicago O'Hare Intl

Tue 22/9

5:30 p.m.-11:10 p.m.

1 stop6h 40m

C$ 483

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 18/8

4:15 p.m.-4:40 p.m.

2 stops23h 25m

Chicago O'Hare Intl

Tue 25/8

5:30 p.m.-1:00 a.m.

1 stop8h 30m

C$ 496

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 25/8

10:10 a.m.-4:40 p.m.

2 stops29h 30m

Chicago O'Hare Intl

Mon 31/8

5:30 p.m.-1:00 a.m.

1 stop8h 30m

C$ 507

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 2/9

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

1 stop8h 40m

Chicago O'Hare Intl

Sat 5/9

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

1 stop8h 40m

C$ 512

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Mon 19/10

7:50 p.m.-9:00 a.m.

1 stop12h 10m

Chicago O'Hare Intl

Wed 21/10

3:45 p.m.-11:16 p.m.

1 stop8h 31m

C$ 522

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Tue 20/10

7:00 a.m.-6:05 p.m.

2 stops10h 05m

Chicago Midway

Sat 24/10

12:28 p.m.-1:00 a.m.

2 stops13h 32m

C$ 523

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Mon 19/10

6:00 a.m.-6:25 p.m.

2 stops11h 25m

Chicago O'Hare Intl

Wed 21/10

2:00 p.m.-11:10 p.m.

2 stops10h 10m

C$ 523

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 7/9

2:15 p.m.-10:05 p.m.

1 stop6h 50m

Chicago O'Hare Intl

Fri 11/9

5:55 a.m.-9:30 p.m.

1 stop16h 35m

C$ 597

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 2/8

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

1 stop13h 59m

Chicago O'Hare Intl

Sun 9/8

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

1 stop16h 30m

C$ 689

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 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

What is the cheapest month to fly to Chicago?

The month of December is another great option to travel to Chicago, with average flight prices from Saskatchewan averaging around C$ 181.

Can stopping save me money on Saskatchewan to Chicago flights?

You could potentially save up to 14% 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

6h 16m

Direct flights

None
The fastest flight from Saskatchewan to Chicago takes 6h 16m
There are no direct flights from Saskatchewan to Chicago. There are no popular flight routes from Saskatchewan to Chicago.
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Frequently asked questions about flying from Saskatchewan to Chicago

  • 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$ 180Free CancellationRating
7.2
3,398 reviews
Search WestJet flights

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 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.

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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