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C$ 85+ Cheap flights from Wisconsin

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 29/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MKE — YYZ
24 Mar — 31 Mar1
1 adult
1 adult, Economy, 0 bags

What to know about flights from Wisconsin

Discover essential information about flights departing from Wisconsin, including flight schedules, destinations, airlines operating at the Wisconsin airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 22 February 2026.

Good round-trip deal

C$ 460 or less

Good one-way deal

C$ 142 or less
Price to beat on a round-trip flight from Wisconsin.
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Price to beat on a one-way flight from Wisconsin.
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Find flights from Wisconsin

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Cheapest flights from Wisconsin
Explore the most affordable flight options available from Wisconsin. Find the lowest fares based on data from user searches, with prices last updated on 22 February 2026.

Fri 8/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Mon 11/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 20/2C$ 220
Thu 30/45:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Mon 4/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 20/2C$ 222
Sun 26/45:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Mon 27/412:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 22/2C$ 223
Thu 7/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Mon 11/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 19/2C$ 237
Thu 26/38:40 p.m.
ORD
-
YYZ
Nonstop1h 39m
Air Canada
Mon 30/38:15 a.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Deal found 19/2C$ 254
Fri 24/42:20 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Mon 27/412:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 19/2C$ 256
Mon 6/49:50 a.m.
ORD
-
YYZ
Nonstop1h 36m
Air Canada
Mon 13/412:05 p.m.
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Deal found 19/2C$ 256
Sun 5/46:40 p.m.
ORD
-
YYZ
Nonstop1h 43m
Air Canada
Sun 12/48:15 a.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Deal found 19/2C$ 260
Wed 27/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Sun 31/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Deal found 18/2C$ 264
Wed 25/36:00 a.m.
ORD
-
YUL
1 stop6h 28m
United Airlines
Wed 25/34:45 p.m.
YUL
-
ORD
Nonstop3h 00m
United Airlines
Deal found 19/2C$ 265
Sun 5/412:50 p.m.
ORD
-
YTZ
1 stop6h 02m
Air Canada
Sun 12/46:45 a.m.
YTZ
-
ORD
1 stop5h 08m
Air Canada
Deal found 19/2C$ 265
Thu 28/57:42 p.m.
ORD
-
YYC
Nonstop3h 55m
United Airlines
Sun 31/58:30 a.m.
YYC
-
ORD
Nonstop3h 37m
United Airlines
Deal found 20/2C$ 275

Find flights from Wisconsin within your budget

 
Find flights departing from Wisconsin that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 22 February 2026. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Pearson Intl

Route

Depart

Return

Price

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Sun 5/4

12:50 p.m.-7:52 p.m.

1 stop6h 02m

Toronto Island

Sun 12/4

6:45 a.m.-10:53 a.m.

1 stop5h 08m

C$ 272

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 30/5

7:42 p.m.-10:37 p.m.

Nonstop3h 55m

Calgary

Wed 3/6

12:28 p.m.-5:05 p.m.

Nonstop3h 37m

C$ 275

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 1/6

7:42 p.m.-10:37 p.m.

Nonstop3h 55m

Calgary

Fri 5/6

8:30 a.m.-1:07 p.m.

Nonstop3h 37m

C$ 275

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Sun 5/4

7:13 a.m.-10:40 a.m.

Nonstop2h 27m

Montreal Pierre Elliott Trudeau Intl

Thu 9/4

9:45 a.m.-11:37 a.m.

Nonstop2h 52m

C$ 293

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Mon 16/3

6:00 p.m.-9:17 p.m.

Nonstop2h 17m

Montreal Pierre Elliott Trudeau Intl

Wed 18/3

6:00 a.m.-8:00 a.m.

Nonstop3h 00m

C$ 294

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Thu 2/4

2:00 p.m.-5:30 p.m.

Nonstop2h 30m

Montreal Pierre Elliott Trudeau Intl

Mon 6/4

6:10 a.m.-8:00 a.m.

Nonstop2h 50m

C$ 294

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Tue 28/4

7:13 a.m.-10:40 a.m.

Nonstop2h 27m

Montreal Pierre Elliott Trudeau Intl

Sun 3/5

9:45 a.m.-11:28 a.m.

Nonstop2h 43m

C$ 294

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Thu 30/4

7:13 a.m.-10:40 a.m.

Nonstop2h 27m

Montreal Pierre Elliott Trudeau Intl

Sun 3/5

6:10 a.m.-8:00 a.m.

Nonstop2h 50m

C$ 294

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Thu 9/4

7:13 a.m.-10:40 a.m.

Nonstop2h 27m

Montreal Pierre Elliott Trudeau Intl

Sun 12/4

6:10 a.m.-8:00 a.m.

Nonstop2h 50m

C$ 294

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Wed 15/4

8:40 a.m.-3:52 p.m.

1 stop6h 12m

Toronto Island

Sat 18/4

6:45 a.m.-10:53 a.m.

1 stop5h 08m

C$ 316

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/2

Showing 1-10 of 60 results
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Best time to book a flight from Wisconsin

Have a flexible travel schedule? Discover the best time to fly from Wisconsin 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.

Travel insights for flights from Wisconsin

Get recent, data-driven insights about flights from Wisconsin including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Wisconsin?

Currently, May is the cheapest month in which you can book a flight from Wisconsin (average of C$ 196). Flying from Wisconsin in August will prove the most costly (average of C$ 745). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

What is the cheapest place to fly to from Wisconsin?

The cheapest city to fly to from Wisconsin is Dallas/Fort Worth, with prices starting at C$ 142. Explore other affordable destinations below.

Dallas/Fort Worth
Dallas/Fort Worth
From C$ 142
Chicago
Chicago
From C$ 395
Charlotte Douglas
Charlotte Douglas
From C$ 1,928

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Related info for your journey

Access useful and relevant information related to your journey from Wisconsin. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 22 February 2026.

  • What is the cheapest month to fly from Wisconsin?

    At the present moment the cheapest month to fly from Wisconsin is currently May; with August being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

  • How does Cheapflights help users find flights from Wisconsin?

    Cheapflights helps you search for flights from Wisconsin via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

  • Why should you use Cheapflights to find cheap flight tickets from Wisconsin?

    Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Wisconsin for you. Better yet — we are completely free to use.

  • Can Cheapflights find flights from Wisconsin with no change fees?

    Certainly. Search results for flights from Wisconsin shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

  • Can Cheapflights notify me if prices for flights from Wisconsin become cheaper?

    Not ready to book yet? You can track prices for flights from Wisconsin on Cheapflights with our Price Alerts feature and get notified when better prices are available.

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How does Cheapflights help users find flights from Wisconsin?

Cheapflights helps you search for flights from Wisconsin via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Wisconsin for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Wisconsin with no change fees?

Certainly. Search results for flights from Wisconsin shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Wisconsin become cheaper?

Not ready to book yet? You can track prices for flights from Wisconsin on Cheapflights with our Price Alerts feature and get notified when better prices are available.

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