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Cheap flights from Saskatchewan to Chicago from C$ 220

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 7/5. 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

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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. - 1:00 a.m.
ORD
-
YXE
8h 30m
1 stop
C$ 372WestJet
sø., 10 mai - lø., 23 mai
WestJet Logo
8:00 a.m. - 4:40 p.m.
YXE
-
ORD
7h 40m
1 stop
WestJet Logo
5:30 p.m. - 11:10 p.m.
ORD
-
YXE
6h 40m
1 stop
C$ 375WestJet
sø., 26 apr. - sø., 3 mai
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 11:20 p.m.
ORD
-
YQR
6h 50m
1 stop
C$ 379WestJet
sø., 10 mai - to., 14 mai
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$ 379WestJet
to., 28 mai - on., 10 jun.
WestJet Logo
8:50 a.m. - 4:40 p.m.
YXE
-
ORD
6h 50m
1 stop
WestJet Logo
5:30 p.m. - 1:00 a.m.
ORD
-
YXE
8h 30m
1 stop
C$ 382WestJet
sø., 26 apr. - to., 30 apr.
WestJet Logo
7:00 a.m. - 4:40 p.m.
YXE
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 1:00 a.m.
ORD
-
YXE
8h 30m
1 stop
C$ 419WestJet
lø., 30 mai - on., 10 jun.
Delta Logo
7:00 a.m. - 8:31 p.m.
YXE
-
ORD
12h 31m
2 stops
Delta Logo
11:30 a.m. - 11:10 p.m.
ORD
-
YXE
12h 40m
2 stops
C$ 458Delta
to., 18 jun. - ma., 22 jun.
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$ 462United Airlines
on., 17 jun. - lø., 20 jun.
Delta Logo
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
Delta Logo
7:01 a.m. - 5:20 p.m.
ORD
-
YQR
11h 19m
2 stops
C$ 465Delta
fr., 5 jun. - ma., 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$ 505Air Canada
fr., 5 jun. - ma., 8 jun.

Air Canada flights from Saskatchewan to Chicago

Our best Air Canada deals on Saskatchewan to Chicago flight tickets
Air Canada
30 May
YXE6:00 a.m.Saskatoon
7h 55m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
6 Jun
ORD9:55 a.m.Chicago O'Hare Intl
14h 21m
1 stop
YXE11:16 p.m.Saskatoon
C$ 476
Air Canada
30 May
YXE6:00 a.m.Saskatoon
13h 08m
2 stops
ORD8:08 p.m.Chicago O'Hare Intl
6 Jun
ORD9:55 a.m.Chicago O'Hare Intl
14h 21m
1 stop
YXE11:16 p.m.Saskatoon
C$ 487
Air Canada
5 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$ 505

Delta flights from Saskatchewan to Chicago

Our best Delta deals on Saskatchewan to Chicago flight tickets
Delta
18 Jun
YXE7:00 a.m.Saskatoon
12h 31m
2 stops
ORD8:31 p.m.Chicago O'Hare Intl
22 Jun
ORD11:30 a.m.Chicago O'Hare Intl
12h 40m
2 stops
YXE11:10 p.m.Saskatoon
C$ 458
Delta
5 Jun
YQR8:35 a.m.Regina
7h 05m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
8 Jun
ORD7:01 a.m.Chicago O'Hare Intl
11h 19m
2 stops
YQR5:20 p.m.Regina
C$ 465
Delta
5 Jun
YQR10:45 a.m.Regina
8h 29m
2 stops
ORD8:14 p.m.Chicago O'Hare Intl
8 Jun
ORD7:01 a.m.Chicago O'Hare Intl
11h 19m
2 stops
YQR5:20 p.m.Regina
C$ 473

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 27 mars 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

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

sø. 10/5

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

1 stop6h 50m

Chicago O'Hare Intl

lø. 23/5

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

1 stop8h 30m

C$ 372
Quickest round-trip

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

sø. 26/4

8:00 a.m.-4:40 p.m.

1 stop7h 40m

Chicago O'Hare Intl

sø. 3/5

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

1 stop6h 40m

C$ 375

ReginaChicago

YQR - ORD

YQRORD

Regina

sø. 10/5

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

1 stop8h 40m

Chicago O'Hare Intl

to. 14/5

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

1 stop6h 50m

C$ 379

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

to. 28/5

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

1 stop8h 40m

Chicago O'Hare Intl

on. 10/6

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

1 stop6h 40m

C$ 379

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

sø. 26/4

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

1 stop6h 50m

Chicago O'Hare Intl

to. 30/4

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

1 stop8h 30m

C$ 382

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

lø. 30/5

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

1 stop8h 40m

Chicago O'Hare Intl

on. 10/6

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

1 stop8h 30m

C$ 419

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

to. 18/6

7:00 a.m.-8:31 p.m.

2 stops12h 31m

Chicago O'Hare Intl

ma. 22/6

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

2 stops12h 40m

C$ 458

ReginaChicago

YQR - ORD

YQRORD

Regina

on. 17/6

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

1 stop13h 59m

Chicago O'Hare Intl

lø. 20/6

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

1 stop16h 30m

C$ 462

ReginaChicago

YQR - ORD

YQRORD

Regina

fr. 5/6

8:35 a.m.-4:40 p.m.

1 stop7h 05m

Chicago O'Hare Intl

ma. 8/6

7:01 a.m.-5:20 p.m.

2 stops11h 19m

C$ 465

ReginaChicago

YQR - ORD

YQRORD

Regina

fr. 5/6

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

1 stop8h 10m

Chicago O'Hare Intl

ma. 8/6

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

1 stop13h 42m

C$ 505

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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

6h 22m

Direct flights

None
The fastest flight from Saskatchewan to Chicago takes 6h 22m
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$ 175Free CancellationRating
7.2
3,302 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 311Free CancellationRating
7.4
9,491 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 411Free CancellationRating
7.1
10,844 reviews
Search Air Canada 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 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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1 adult
sø. 26/4
sø. 3/5
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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