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Cheap flights from Calgary to Milwaukee from C$ 285

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 24/12. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MKE
16 Oct — 23 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Calgary to Milwaukee

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Milwaukee (MKE). 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 September 2025.

Round-trip from

C$ 606

One-way from

C$ 285

Popular in

January

Cheapest in

October

Average price

C$ 746
American Airlines
  • American Airlines
  • 9/10-13/10
  • 2 total stops
  • 26h 45m total
  • Calgary to Milwaukee
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United Airlines
  • United Airlines
  • 24/12
  • 1 total stop
  • 23h 50m total
  • Calgary to Milwaukee
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Highest demand for flights based on searches. 9% potential increase in price (C$ 106 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 57 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Calgary to Milwaukee

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

Thu 9/101:29 p.m.YYC - MKE
1 stop9h 27mAmerican Airlines
Mon 13/108:16 p.m.MKE - YYC
1 stop17h 18mAmerican Airlines
Deal found 15/9C$ 606
Thu 9/106:30 a.m.YYC - MKE
2 stops10h 52mMultiple Airlines
Mon 13/107:38 p.m.MKE - YYC
3 stops25h 22mMultiple Airlines
Deal found 15/9C$ 624
Sat 27/126:10 a.m.YYC - MKE
1 stop15h 05mUnited Airlines
Fri 2/14:11 p.m.MKE - YYC
1 stop6h 42mUnited Airlines
Deal found 15/9C$ 725
Fri 7/116:45 a.m.YYC - MKE
1 stop11h 08mMultiple Airlines
Sun 9/116:25 p.m.MKE - YYC
2 stops25h 50mMultiple Airlines
Deal found 16/9C$ 778
Sat 27/1210:00 a.m.YYC - MKE
2 stops29h 44mWestJet
Fri 2/16:35 a.m.MKE - YYC
2 stops10h 40mWestJet
Deal found 15/9C$ 783
Sat 8/112:13 p.m.YYC - MKE
1 stop6h 10mUnited Airlines
Sun 9/118:15 a.m.MKE - YYC
1 stop14h 38mUnited Airlines
Deal found 16/9C$ 786
Fri 7/111:00 a.m.YYC - MKE
2 stops10h 30mWestJet
Sun 9/116:00 a.m.MKE - YYC
2 stops11h 16mWestJet
Deal found 16/9C$ 787
Thu 6/1112:15 a.m.YYC - MKE
2 stops11h 10mWestJet
Sun 9/116:00 a.m.MKE - YYC
2 stops11h 16mWestJet
Deal found 16/9C$ 793
Sat 8/116:45 a.m.YYC - MKE
1 stop10h 27mMultiple Airlines
Sun 9/1111:57 a.m.MKE - YYC
2 stops20h 08mMultiple Airlines
Deal found 16/9C$ 812

Cheapflights Fare Finder

 
Customize your flight search to find flights from Calgary to Milwaukee 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 September 2025.
Use the filters below to find and compare flights from Calgary to Milwaukee that are best for you.

Fly from

Calgary

Fly to

Milwaukee

Route

Depart

Return

Price

CalgaryMilwaukee

YYC - MKE

YYCMKE

Calgary

Thu 9/10

1:29 p.m.-11:56 p.m.

1 stop9h 27m

Milwaukee-Mitchell

Mon 13/10

8:16 p.m.-12:34 p.m.

1 stop17h 18m

C$ 606

CalgaryMilwaukee

YYC - MKE

YYCMKE

Calgary

Thu 9/10

6:30 a.m.-6:22 p.m.

2 stops10h 52m

Milwaukee-Mitchell

Mon 13/10

7:38 p.m.-8:00 p.m.

3 stops25h 22m

C$ 624

CalgaryMilwaukee

YYC - MKE

YYCMKE

Calgary

Sat 27/12

6:10 a.m.-10:15 p.m.

1 stop15h 05m

Milwaukee-Mitchell

Fri 2/1

4:11 p.m.-9:53 p.m.

1 stop6h 42m

C$ 725

CalgaryMilwaukee

YYC - MKE

YYCMKE

Calgary

Fri 7/11

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

1 stop11h 08m

Milwaukee-Mitchell

Sun 9/11

6:25 p.m.-7:15 p.m.

2 stops25h 50m

C$ 778

CalgaryMilwaukee

YYC - MKE

YYCMKE

Calgary

Sat 27/12

10:00 a.m.-4:44 p.m.

2 stops29h 44m

Milwaukee-Mitchell

Fri 2/1

6:35 a.m.-4:15 p.m.

2 stops10h 40m

C$ 783

CalgaryMilwaukee

YYC - MKE

YYCMKE

Calgary

Sat 8/11

2:13 p.m.-9:23 p.m.

1 stop6h 10m

Milwaukee-Mitchell

Sun 9/11

8:15 a.m.-9:53 p.m.

1 stop14h 38m

C$ 786

CalgaryMilwaukee

YYC - MKE

YYCMKE

Calgary

Fri 7/11

1:00 a.m.-12:30 p.m.

2 stops10h 30m

Milwaukee-Mitchell

Sun 9/11

6:00 a.m.-4:16 p.m.

2 stops11h 16m

C$ 787

CalgaryMilwaukee

YYC - MKE

YYCMKE

Calgary

Wed 24/12

2:10 p.m.-3:00 p.m.

1 stop23h 50m

C$ 285

CalgaryMilwaukee

YYC - MKE

YYCMKE

Calgary

Wed 24/12

2:35 p.m.-1:28 p.m.

2 stops21h 53m

C$ 303

CalgaryMilwaukee

YYC - MKE

YYCMKE

Calgary

Sat 8/11

11:40 p.m.-7:19 p.m.

3 stops42h 39m

C$ 307

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

Showing 1-10 of 17 results
1
2

Best time to book a flight from Calgary to Milwaukee

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

Cheapflights Insights

Everything you need to know about your flight from Calgary to Milwaukee

What is the cheapest month to book a flight from Calgary to Milwaukee?

Currently, January is the cheapest month in which you can book a flight from Calgary to Milwaukee (average of C$ 339). Flying from Calgary to Milwaukee in July is currently the most expensive (average of C$ 484). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Calgary to Milwaukee?

Reviews of airlines servicing Milwaukee

Get insights into the airlines that provide service to Milwaukee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Milwaukee. Reviews last updated 16 September 2025.
Check out reviews from past customers who have flown with WestJet from Calgary to Milwaukee to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,093 reviews
Check prices

Comfort

7.1

Overall

7.2

Boarding

7.4

Entertainment

6.1

Food

6.2

Crew

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

YYC - NRT

I like direct flight from Calgary to Japan. But it’s my fault, I did not decide my seat till last minute. I was in the middle seat in the middle lane, I hesitated asking to go to bathroom.
WestJet
7.2
Good
3,093 reviews
WestJet
7.2
Good
3,093 reviews
Check prices

Comfort

7.1

Overall

7.2

Boarding

7.4

Entertainment

6.1

Food

6.2

Crew

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

YYC - NRT

I like direct flight from Calgary to Japan. But it’s my fault, I did not decide my seat till last minute. I was in the middle seat in the middle lane, I hesitated asking to go to bathroom.

Related info for your journey

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

  • How long is the flight from Calgary to Milwaukee?

    Departing from Calgary to Milwaukee will take you 9h 27m. Calgary and Milwaukee are separated by a distance of 2161 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What is the cheapest airline to fly from Calgary to Milwaukee round-trip?

    WestJet, at C$ 560, was found to be the cheapest airline from Calgary to Milwaukee.. WestJet is currently priced 28% below the average price you’ll pay for this route.

  • Can I find deals for flights from Calgary to Milwaukee that include hotel bookings?

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

  • How can I find direct flights from Calgary to Milwaukee?

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

  • Can I find deals for business class flights from Calgary to Milwaukee?

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

  • What is the cheapest month to book a flight from Calgary to Milwaukee?

    Currently, January is the cheapest month in which you can book a flight from Calgary to Milwaukee (average of C$ 339). Flying from Calgary to Milwaukee in July is currently the most expensive (average of C$ 484). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Calgary to Milwaukee

Discover the top airline that operate flights from Calgary to Milwaukee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 16 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 560AverageC$ 736FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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How does Cheapflights help users find flights from Calgary to Milwaukee?

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Can Cheapflights find flights from Calgary to Milwaukee with no change fees?

Need flexible booking options for your flight to Milwaukee from Calgary? 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 Calgary to Milwaukee become cheaper?

Yes! Start tracking prices for Calgary to Milwaukee flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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