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Cheap flights from Saskatoon to Chicago from C$ 280

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Saskatoon to Chicago departing on 19/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Saskatoon to Chicago (YXE-MDW)

Cheap round-trip flights

Delta Logo
5:20 a.m. - 5:35 p.m.YXE-MDW
11h 15m2 stops
Delta Logo
1:43 p.m. - 9:24 p.m.MDW-YXE
8h 41m1 stop
C$ 664Delta
Find Deal
mié., 17 sep. - mié., 24 sep.
Logo
5:40 a.m. - 5:35 p.m.YXE-MDW
10h 55m2 stops
Logo
9:20 a.m. - 11:20 a.m.MDW-YXE
27h 00m2 stops
C$ 738
Find Deal
mié., 17 sep. - mié., 24 sep.
WestJet Logo
5:40 a.m. - 5:35 p.m.YXE-MDW
10h 55m2 stops
WestJet Logo
9:20 a.m. - 7:40 p.m.MDW-YXE
11h 20m2 stops
C$ 794WestJet
Find Deal
jue., 2 oct. - lun., 6 oct.
Logo
5:40 a.m. - 5:35 p.m.YXE-MDW
10h 55m2 stops
Logo
5:20 p.m. - 12:28 p.m.MDW-YXE
20h 08m3 stops
C$ 851
Find Deal
mié., 17 sep. - mié., 24 sep.
WestJet Logo
5:40 a.m. - 5:35 p.m.YXE-MDW
10h 55m2 stops
WestJet Logo
9:20 a.m. - 7:40 p.m.MDW-YXE
11h 20m2 stops
C$ 901WestJet
Find Deal
jue., 2 oct. - lun., 6 oct.
WestJet Logo
5:40 a.m. - 5:37 p.m.YXE-MDW
10h 57m2 stops
WestJet Logo
9:15 a.m. - 9:24 p.m.MDW-YXE
13h 09m1 stop
C$ 929WestJet
Find Deal
sáb., 30 ago. - sáb., 6 sep.
WestJet Logo
5:40 a.m. - 5:35 p.m.YXE-MDW
10h 55m2 stops
WestJet Logo
1:48 p.m. - 9:24 p.m.MDW-YXE
8h 36m1 stop
C$ 931WestJet
Find Deal
jue., 2 oct. - lun., 6 oct.
WestJet Logo
5:40 a.m. - 5:35 p.m.YXE-MDW
10h 55m2 stops
WestJet Logo
1:48 p.m. - 9:24 p.m.MDW-YXE
8h 36m1 stop
C$ 934WestJet
Find Deal
jue., 2 oct. - lun., 6 oct.
WestJet Logo
5:40 a.m. - 5:35 p.m.YXE-MDW
10h 55m2 stops
WestJet Logo
9:20 a.m. - 7:47 p.m.MDW-YXE
11h 27m2 stops
C$ 1,064WestJet
Find Deal
jue., 25 sep. - lun., 29 sep.
WestJet Logo
5:40 a.m. - 5:35 p.m.YXE-MDW
10h 55m2 stops
WestJet Logo
9:20 a.m. - 6:03 p.m.MDW-YXE
9h 43m2 stops
C$ 1,097WestJet
Find Deal
jue., 25 sep. - dom., 28 sep.

WestJet flights from Saskatoon to Chicago Midway Airport

Our best WestJet deals on Saskatoon to Chicago Midway Airport flight tickets
WestJet
2 Oct
YXE5:40 a.m.Saskatoon
10h 55m
2 stops
MDW5:35 p.m.Chicago Midway
6 Oct
MDW9:20 a.m.Chicago Midway
11h 20m
2 stops
YXE7:40 p.m.Saskatoon
C$ 794
Find similar
WestJet
2 Oct
YXE5:40 a.m.Saskatoon
10h 55m
2 stops
MDW5:35 p.m.Chicago Midway
6 Oct
MDW9:20 a.m.Chicago Midway
11h 20m
2 stops
YXE7:40 p.m.Saskatoon
C$ 901
Find similar
WestJet
30 Aug
YXE5:40 a.m.Saskatoon
10h 57m
2 stops
MDW5:37 p.m.Chicago Midway
6 Sep
MDW9:15 a.m.Chicago Midway
13h 09m
1 stop
YXE9:24 p.m.Saskatoon
C$ 929
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Saskatoon to Chicago Midway Airport 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 5 agosto 2025.
Use the filters below to find and compare flights from Saskatoon to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

mié. 17/9

5:20 a.m.-5:35 p.m.

2 stops11h 15m

Chicago Midway

mié. 24/9

1:43 p.m.-9:24 p.m.

1 stop8h 41m

C$ 664

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

mié. 17/9

5:40 a.m.-5:35 p.m.

2 stops10h 55m

Chicago Midway

mié. 24/9

9:20 a.m.-11:20 a.m.

2 stops27h 00m

C$ 738

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

jue. 2/10

5:40 a.m.-5:35 p.m.

2 stops10h 55m

Chicago Midway

lun. 6/10

9:20 a.m.-7:40 p.m.

2 stops11h 20m

C$ 794

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

mié. 17/9

5:40 a.m.-5:35 p.m.

2 stops10h 55m

Chicago Midway

mié. 24/9

5:20 p.m.-12:28 p.m.

3 stops20h 08m

C$ 851

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

jue. 2/10

5:40 a.m.-5:35 p.m.

2 stops10h 55m

Chicago Midway

lun. 6/10

9:20 a.m.-7:40 p.m.

2 stops11h 20m

C$ 901

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

sáb. 30/8

5:40 a.m.-5:37 p.m.

2 stops10h 57m

Chicago Midway

sáb. 6/9

9:15 a.m.-9:24 p.m.

1 stop13h 09m

C$ 929

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

jue. 2/10

5:40 a.m.-5:35 p.m.

2 stops10h 55m

Chicago Midway

lun. 6/10

1:48 p.m.-9:24 p.m.

1 stop8h 36m

C$ 931

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

jue. 2/10

5:40 a.m.-5:35 p.m.

2 stops10h 55m

Chicago Midway

lun. 6/10

1:48 p.m.-9:24 p.m.

1 stop8h 36m

C$ 934

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

jue. 25/9

5:40 a.m.-5:35 p.m.

2 stops10h 55m

Chicago Midway

lun. 29/9

9:20 a.m.-7:47 p.m.

2 stops11h 27m

C$ 1,064

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

jue. 25/9

5:40 a.m.-5:35 p.m.

2 stops10h 55m

Chicago Midway

dom. 28/9

9:20 a.m.-6:03 p.m.

2 stops9h 43m

C$ 1,097

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Saskatoon to Chicago Midway Airport

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 airline that flies from Saskatoon to Chicago Midway?

Delta and WestJet are the most popular carriers operating from Saskatoon to Chicago Midway

When to book flights from Saskatoon to Chicago Midway Airport

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

Cheap Saskatoon to Chicago Midway Airport (YXE to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Saskatoon to Chicago Midway Airport

Best price found

C$ 280

Fastest flight time

10h 55m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Saskatoon in the past 72 hours is C$ 280. The best round-trip flight deal from Saskatoon to Chicago Midway Airport found on momondo in the last 72 hours is C$ 664.
The fastest flight from Saskatoon to Chicago Midway Airport takes 10h 55m
There are no direct flights from Saskatoon to Chicago Midway Airport. Popular non-direct route for this connection is Saskatoon Airport - Chicago Midway Airport.
Search flight deals

  • How far is Saskatoon to Chicago Midway by plane?

    The distance between Saskatoon and Chicago Midway is about 1829.4 km. In terms of flight time, this usually takes a little over 10h 55m.

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

    Prices for flights from Saskatoon Airport to Chicago Midway Airport refresh daily.

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

    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 Saskatoon Airport to Chicago Midway Airport.

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

    The travel and health documents required for your trip to Chicago Midway Airport 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 Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Travelling to a place near Chicago?

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

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Saskatoon to Chicago . Millions of users trust and use momondo every year so you are in good hands.

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

Yes. All flights to Chicago from Saskatoon on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo provides multiple filters to help you find the best flight to Chicago from Saskatoon. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Of course. momondo tracks the price of Saskatoon to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago Midway Airport trip

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