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Cheap flights from Saskatoon to Chicago from C$ 338

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 20/5. 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 Saskatoon to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 a.m. - 6:31 p.m.
YXE
-
MDW
11h 31m
2 stops
Delta Logo
1:00 p.m. - 1:00 a.m.
MDW
-
YXE
13h 00m
2 stops
C$ 530Delta
Wed, 23 Sep - Sat, 26 Sep
Delta Logo
6:00 a.m. - 6:31 p.m.
YXE
-
MDW
11h 31m
2 stops
Delta Logo
1:00 p.m. - 11:10 p.m.
MDW
-
YXE
11h 10m
2 stops
C$ 550Delta
Wed, 23 Sep - Sat, 26 Sep
Delta Logo
6:00 a.m. - 6:31 p.m.
YXE
-
MDW
11h 31m
2 stops
Delta Logo
1:00 p.m. - 11:10 p.m.
MDW
-
YXE
11h 10m
2 stops
C$ 551Delta
Wed, 23 Sep - Sat, 26 Sep
Delta Logo
6:00 a.m. - 6:31 p.m.
YXE
-
MDW
11h 31m
2 stops
Delta Logo
1:00 p.m. - 11:10 p.m.
MDW
-
YXE
11h 10m
2 stops
C$ 562Delta
Wed, 23 Sep - Sat, 26 Sep
Delta Logo
6:00 a.m. - 6:33 p.m.
YXE
-
MDW
11h 33m
2 stops
Delta Logo
1:27 p.m. - 1:00 a.m.
MDW
-
YXE
12h 33m
2 stops
C$ 600Delta
Thu, 6 Aug - Mon, 10 Aug
Delta Logo
6:00 a.m. - 6:33 p.m.
YXE
-
MDW
11h 33m
2 stops
Delta Logo
1:27 p.m. - 1:00 a.m.
MDW
-
YXE
12h 33m
2 stops
C$ 601Delta
Wed, 12 Aug - Thu, 20 Aug
Delta Logo
6:00 a.m. - 6:33 p.m.
YXE
-
MDW
11h 33m
2 stops
Delta Logo
1:52 p.m. - 9:35 p.m.
MDW
-
YXE
8h 43m
1 stop
C$ 612Delta
Fri, 7 Aug - Thu, 13 Aug
Delta Logo
7:00 a.m. - 6:31 p.m.
YXE
-
MDW
10h 31m
2 stops
Delta Logo
6:45 p.m. - 9:35 p.m.
MDW
-
YXE
27h 50m
1 stop
C$ 629Delta
Wed, 23 Sep - Sat, 26 Sep
Delta Logo
7:00 a.m. - 6:31 p.m.
YXE
-
MDW
10h 31m
2 stops
Delta Logo
6:45 p.m. - 9:35 p.m.
MDW
-
YXE
27h 50m
1 stop
C$ 690Delta
Wed, 23 Sep - Sat, 26 Sep
Delta Logo
6:00 a.m. - 6:31 p.m.
YXE
-
MDW
11h 31m
2 stops
Delta Logo
6:45 p.m. - 9:35 p.m.
MDW
-
YXE
27h 50m
1 stop
C$ 702Delta
Wed, 23 Sep - Sat, 26 Sep

Delta flights from Saskatoon to Chicago Midway Airport

Our best Delta deals on Saskatoon to Chicago Midway Airport flight tickets
Delta
23 Sep
YXE6:00 a.m.Saskatoon
11h 31m
2 stops
MDW6:31 p.m.Chicago Midway
26 Sep
MDW1:00 p.m.Chicago Midway
13h 00m
2 stops
YXE1:00 a.m.Saskatoon
C$ 530
Delta
23 Sep
YXE6:00 a.m.Saskatoon
11h 31m
2 stops
MDW6:31 p.m.Chicago Midway
26 Sep
MDW1:00 p.m.Chicago Midway
11h 10m
2 stops
YXE11:10 p.m.Saskatoon
C$ 550
Delta
23 Sep
YXE6:00 a.m.Saskatoon
11h 31m
2 stops
MDW6:31 p.m.Chicago Midway
26 Sep
MDW1:00 p.m.Chicago Midway
11h 10m
2 stops
YXE11:10 p.m.Saskatoon
C$ 551

WestJet flights from Saskatoon to Chicago Midway Airport

Our best WestJet deals on Saskatoon to Chicago Midway Airport flight tickets
WestJet
28 May
YXE6:00 a.m.Saskatoon
11h 33m
2 stops
MDW6:33 p.m.Chicago Midway
5 Jun
MDW9:22 a.m.Chicago Midway
16h 38m
3 stops
YXE1:00 a.m.Saskatoon
C$ 876
WestJet
28 May
YXE6:00 a.m.Saskatoon
11h 33m
2 stops
MDW6:33 p.m.Chicago Midway
5 Jun
MDW9:22 a.m.Chicago Midway
16h 13m
2 stops
YXE12:35 a.m.Saskatoon
C$ 884
WestJet
12 Sep
YXE6:00 a.m.Saskatoon
11h 31m
2 stops
MDW6:31 p.m.Chicago Midway
17 Sep
MDW1:00 p.m.Chicago Midway
12h 35m
2 stops
YXE12:35 a.m.Saskatoon
C$ 885

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 8 May 2026.
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

Cheapest round-trip

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Wed 23/9

6:00 a.m.-6:31 p.m.

2 stops11h 31m

Chicago Midway

Sat 26/9

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

2 stops13h 00m

C$ 530

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Wed 23/9

6:00 a.m.-6:31 p.m.

2 stops11h 31m

Chicago Midway

Sat 26/9

1:00 p.m.-11:10 p.m.

2 stops11h 10m

C$ 550

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Wed 23/9

6:00 a.m.-6:31 p.m.

2 stops11h 31m

Chicago Midway

Sat 26/9

1:00 p.m.-11:10 p.m.

2 stops11h 10m

C$ 551

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Wed 23/9

6:00 a.m.-6:31 p.m.

2 stops11h 31m

Chicago Midway

Sat 26/9

1:00 p.m.-11:10 p.m.

2 stops11h 10m

C$ 562

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Thu 6/8

6:00 a.m.-6:33 p.m.

2 stops11h 33m

Chicago Midway

Mon 10/8

1:27 p.m.-1:00 a.m.

2 stops12h 33m

C$ 600

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Wed 12/8

6:00 a.m.-6:33 p.m.

2 stops11h 33m

Chicago Midway

Thu 20/8

1:27 p.m.-1:00 a.m.

2 stops12h 33m

C$ 601
Quickest round-trip

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Fri 7/8

6:00 a.m.-6:33 p.m.

2 stops11h 33m

Chicago Midway

Thu 13/8

1:52 p.m.-9:35 p.m.

1 stop8h 43m

C$ 612

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Wed 23/9

7:00 a.m.-6:31 p.m.

2 stops10h 31m

Chicago Midway

Sat 26/9

6:45 p.m.-9:35 p.m.

1 stop27h 50m

C$ 629

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Wed 23/9

7:00 a.m.-6:31 p.m.

2 stops10h 31m

Chicago Midway

Sat 26/9

6:45 p.m.-9:35 p.m.

1 stop27h 50m

C$ 690

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Wed 23/9

6:00 a.m.-6:31 p.m.

2 stops11h 31m

Chicago Midway

Sat 26/9

6:45 p.m.-9:35 p.m.

1 stop27h 50m

C$ 702

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 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

Can stopping save me money on Saskatoon to Chicago Midway Airport flights?

You could potentially save up to 48% on your flight if you consider stops on a Saskatoon to Chicago Midway Airport flight.

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

Fastest flight time

10h 33m

Direct flights

None
The fastest flight from Saskatoon to Chicago Midway Airport takes 10h 33m
There are no direct flights from Saskatoon to Chicago Midway Airport. There are no popular flight routes from Saskatoon to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Saskatoon to Chicago Midway Airport

  • 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 33m.

  • 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
Merrillville
Hammond
Munster

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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