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Cheap flights from Saskatoon to Chicago Midway Airport from C$ 699

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — MDW
15 Jan — 22 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Saskatoon to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Saskatoon to Midway
Explore the most affordable flight options available from Saskatoon to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 16 December 2025.

Tue 30/129:45 p.m.YXE - MDW
2 stops23h 00mMultiple Airlines
Tue 6/12:03 p.m.MDW - YXE
1 stop9h 54mMultiple Airlines
Deal found 15/12C$ 980
Mon 29/127:00 a.m.YXE - MDW
2 stops25h 49mWestJet
Mon 5/111:21 a.m.MDW - YXE
2 stops38h 12mWestJet
Deal found 15/12C$ 1,006
Tue 30/124:35 p.m.YXE - MDW
2 stops42h 31mWestJet
Tue 6/17:16 p.m.MDW - YXE
2 stops30h 33mWestJet
Deal found 15/12C$ 1,181
Sat 20/127:00 a.m.YXE - MDW
1 stop27h 05mMultiple Airlines
Sat 3/111:05 a.m.MDW - YXE
1 stop14h 28mMultiple Airlines
Deal found 16/12C$ 1,591
Sat 20/128:35 p.m.YXE - MDW
2 stops14h 31mWestJet
Sat 3/19:50 a.m.MDW - YXE
2 stops39h 43mWestJet
Deal found 16/12C$ 1,621
Mon 29/124:45 p.m.YXE - MDW
2 stops17h 34mMultiple Airlines
Mon 5/17:16 p.m.MDW - YXE
1 stop19h 22mMultiple Airlines
Deal found 14/12C$ 1,840
Sun 21/128:10 a.m.YXE - MDW
1 stop9h 09mWestJet
Sat 3/15:59 p.m.MDW - YXE
1 stop20h 39mWestJet
Deal found 15/12C$ 1,909

Find flight deals from Saskatoon to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Saskatoon (YXE) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 16 December 2025.

Round-trip from

C$ 699

Popular in

February

Cheapest in

September

Average price

C$ 922
Delta
  • Delta
  • 12/1-16/1
  • 4 total stops
  • 56h 41m total
  • Saskatoon to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 141 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 48 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Saskatoon to Midway 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, Cheapflights users made 629,999 searches. Data last updated 16 December 2025.
Use the filters below to find and compare flights from Saskatoon to Chicago Midway Airport that are best for you.

Fly from

Saskatoon

Fly to

Midway

Route

Depart

Return

Price

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Mon 12/1

7:00 a.m.-9:08 a.m.

2 stops26h 08m

Chicago Midway

Fri 16/1

7:16 p.m.-1:49 a.m.

2 stops30h 33m

C$ 699

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sun 11/1

8:10 a.m.-6:32 p.m.

1 stop10h 22m

Chicago Midway

Sun 18/1

9:50 a.m.-2:38 p.m.

1 stop4h 48m

C$ 703

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sun 11/1

7:00 a.m.-12:48 p.m.

2 stops29h 48m

Chicago Midway

Sun 18/1

9:32 a.m.-1:33 a.m.

2 stops16h 01m

C$ 780

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sun 11/1

7:00 a.m.-10:10 a.m.

1 stop27h 10m

Chicago Midway

Sun 18/1

4:15 p.m.-1:24 p.m.

2 stops21h 09m

C$ 961

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Tue 30/12

9:45 p.m.-8:45 p.m.

2 stops23h 00m

Chicago Midway

Tue 6/1

2:03 p.m.-11:57 p.m.

1 stop9h 54m

C$ 980

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Mon 29/12

7:00 a.m.-8:49 a.m.

2 stops25h 49m

Chicago Midway

Mon 5/1

11:21 a.m.-1:33 a.m.

2 stops38h 12m

C$ 1,006

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Thu 8/1

8:10 a.m.-6:32 p.m.

1 stop10h 22m

Chicago Midway

Thu 15/1

9:50 a.m.-2:38 p.m.

1 stop4h 48m

C$ 1,128

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Tue 30/12

4:35 p.m.-11:06 a.m.

2 stops42h 31m

Chicago Midway

Tue 6/1

7:16 p.m.-1:49 a.m.

2 stops30h 33m

C$ 1,181

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/12

Best time to book a flight from Saskatoon to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Saskatoon with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Saskatoon to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Saskatoon to Chicago Midway?

    Located just 4.6 km from the city centre, Saskatoon is the airport most travellers will use when flying to Chicago Midway from Saskatoon. Booking flights from Saskatoon (YXE) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.

  • How long is the flight from Saskatoon to Chicago Midway Airport?

    There are many flights that can get you from Saskatoon to Chicago Midway Airport in 26h 08m. Fly via Delta or WestJet to get the fastest option. The distance from Saskatoon to Chicago Midway Airport is about 1833 km. Both multi-stop and direct flights can be found to your destination and back.

  • Can I find deals for flights from Saskatoon to Midway that include hotel bookings?

    Yes. In addition to deals on Saskatoon to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Saskatoon to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Saskatoon to Midway.

  • Can I find deals for business class flights from Saskatoon to Midway?

    Yes. Cheapflights offers flight deals from Saskatoon to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Saskatoon to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Saskatoon to O'Hare Intl flights
Regina to O'Hare Intl flights

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How does Cheapflights help users find flights from Saskatoon to Midway?

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Why should you use Cheapflights to find cheap flight tickets from Saskatoon to Midway?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Saskatoon to Midway.

Can Cheapflights find flights from Saskatoon to Midway with no change fees?

Need flexible booking options for your flight to Midway from Saskatoon? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Saskatoon to Midway become cheaper?

Of course! You can now track prices for flights from Saskatoon to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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