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Cheap flights from Calgary to Milwaukee from C$ 325

YYC — MKE
15 Oct — 22 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Calgary to Milwaukee

Enter your travel dates to find the best prices.

Cheapest flights from Calgary to Milwaukee

Wed 28/106:35 a.m. -
2 stops12h 31m
Wed 4/119:35 a.m. -
2 stops13h 05m
Deal found 13/9C$ 633
Mon 19/101:51 p.m. -
1 stop17h 16m
Tue 27/1012:21 p.m. -
1 stop10h 24m
Deal found 11/9C$ 649
Sat 12/127:00 a.m. -
1 stop5h 24m
Tue 15/123:59 p.m. -
1 stop7h 54m
Deal found 14/9C$ 661
Tue 17/117:00 a.m. -
1 stop12h 59m
Thu 19/116:47 a.m. -
1 stop6h 48m
Deal found 10/9C$ 665
Tue 20/1012:30 p.m. -
1 stop9h 29m
Wed 21/106:15 a.m. -
1 stop6h 13m
Deal found 11/9C$ 674
Tue 17/117:01 a.m. -
2 stops14h 36m
Thu 19/1112:15 p.m. -
1 stop11h 32m
Deal found 10/9C$ 704
Mon 19/107:00 a.m. -
2 stops11h 30m
Tue 27/106:30 a.m. -
2 stops11h 00m
Deal found 11/9C$ 720
Tue 20/108:20 a.m. -
2 stops11h 53m
Wed 21/106:49 p.m. -
1 stop26h 16m
Deal found 13/9C$ 728

Find flight deals from Calgary to Milwaukee

Round-trip from

C$ 633

One-way from

C$ 325

Popular in

June

Cheapest in

October

Average price

C$ 940
Delta
  • Delta
  • 28/10-4/11
  • 4 total stops
  • 25h 36m total
  • Calgary to Milwaukee
Search Deals
11/10-31/12
  • 11/10-31/12
  • 3 total stops
  • 37h 30m total
  • Calgary to Milwaukee
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Calgary to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgaryMilwaukee

YYC Calgary - MKE Milwaukee-Mitchell

YYCMKE

Calgary

Fri 18/12

1:43 p.m.-8:52 p.m.

1 stop7h 09m

Milwaukee-Mitchell

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 415

CalgaryMilwaukee

YYC Calgary - MKE Milwaukee-Mitchell

YYCMKE

Calgary

Sun 11/10

11:00 a.m.-8:40 a.m.

1 stop20h 40m

Milwaukee-Mitchell

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 418

CalgaryMilwaukee

YYC Calgary - MKE Milwaukee-Mitchell

YYCMKE

Calgary

Sun 11/10

7:00 a.m.-7:30 p.m.

2 stops11h 30m

Milwaukee-Mitchell

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 428

CalgaryMilwaukee

YYC Calgary - MKE Milwaukee-Mitchell

YYCMKE

Calgary

Fri 18/12

12:15 p.m.-9:14 a.m.

2 stops20h 59m

Milwaukee-Mitchell

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 453

CalgaryMilwaukee

YYC Calgary - MKE Milwaukee-Mitchell

YYCMKE

Calgary

Fri 18/12

1:37 p.m.-10:11 p.m.

1 stop8h 34m

Milwaukee-Mitchell

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 460
Quickest round-trip

CalgaryMilwaukee

YYC Calgary - MKE Milwaukee-Mitchell

YYCMKE

Calgary

Wed 23/9

6:00 a.m.-1:34 p.m.

1 stop6h 34m

Milwaukee-Mitchell

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 475

CalgaryMilwaukee

YYC Calgary - MKE Milwaukee-Mitchell

YYCMKE

Calgary

Sun 25/10

9:15 a.m.-9:13 p.m.

3 stops34h 58m

Milwaukee-Mitchell

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 479

CalgaryMilwaukee

YYC Calgary - MKE Milwaukee-Mitchell

YYCMKE

Calgary

Sat 10/10

6:00 a.m.-9:08 p.m.

1 stop14h 08m

Milwaukee-Mitchell

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 483

CalgaryMilwaukee

YYC Calgary - MKE Milwaukee-Mitchell

YYCMKE

Calgary

Thu 8/10

1:51 p.m.-10:42 p.m.

1 stop7h 51m

Milwaukee-Mitchell

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 489

CalgaryMilwaukee

YYC Calgary - MKE Milwaukee-Mitchell

YYCMKE

Calgary

Fri 9/10

6:50 p.m.-7:30 p.m.

3 stops23h 40m

Milwaukee-Mitchell

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 492

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

Showing 1-10 of 19 resultsSorted by cheapest first
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

Cheapflights Insights

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

What’s the top layover airport for flights from Calgary to Milwaukee?

Chicago (ORD) – chosen by Cheapflights users on 50% of one-stop itineraries from Calgary to Milwaukee on Cheapflights.

What’s the cheapest layover airport for flights from Calgary to Milwaukee?

Chicago (ORD) is the most affordable 1-stop option, with an average round-trip price of C$ 730.

What’s the fastest layover option from Calgary to Milwaukee?

Flights via Chicago (ORD) have the shortest average one-way travel time for 1-stop routes: 5h 06m.

Which airport typically offers the quickest layover for flights from Calgary to Milwaukee?

Flights via Detroit (DTW) offer the fastest connection on this route, with an average layover time of 1h 05m.

Reviews of airlines servicing Milwaukee

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
3,443 reviews
Check prices

Overall

7.2

Boarding

7.4

Comfort

7.1

Food

6.2

Entertainment

6.1

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Dec 2023

YYC - PSP

Can never get the influential entertainment to work on the app. Super disappointing.
WestJet
7.2
Good
3,443 reviews
WestJet
7.2
Good
3,443 reviews
Check prices

Overall

7.2

Boarding

7.4

Comfort

7.1

Food

6.2

Entertainment

6.1

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Dec 2023

YYC - PSP

Can never get the influential entertainment to work on the app. Super disappointing.

Related info for your journey

  • How long is the flight from Calgary to Milwaukee?

    Departing from Calgary to Milwaukee will take you 6h 31m. 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$ 504, was found to be the cheapest airline from Calgary to Milwaukee.. WestJet is currently priced 36% 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Top airline flying from Calgary to Milwaukee

AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 504AverageC$ 750FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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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.

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