$171 Find Cheap Flights from Milwaukee to Canada

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milwaukee to Canada departing on 5/23. 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.
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1 adult, Economy, 0 bags

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Cheap Flights from Milwaukee to Canada

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Calgary
Calgary1 stop$438
Halifax
Halifax1 stop$368
Ottawa
Ottawa1 stop$529
Winnipeg
Winnipeg1 stop$431
Québec City
Québec City1 stop$724
Kelowna
Kelowna2 stops$629
Charlottetown
Charlottetown2 stops$914
Calgary
Calgary1 stop$438
Halifax
Halifax1 stop$368
Ottawa
Ottawa1 stop$529
Winnipeg
Winnipeg1 stop$431
Québec City
Québec City1 stop$724
Kelowna
Kelowna2 stops$629
Charlottetown
Charlottetown2 stops$914

Book Cheap Milwaukee to Canada Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to Canada that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Milwaukee to Canada

Sat, Jun 20 - Sat, Jun 27
WestJet Logo
7:05 am - 9:45 pm
MKE
-
YHZ
12h 40m
1 stop
WestJet Logo
3:30 pm - 8:51 am
YHZ
-
MKE
19h 21m
1 stop
$368WestJet
Thu, Aug 13 - Tue, Aug 18
WestJet Logo
6:00 am - 11:27 pm
MKE
-
YHZ
15h 27m
1 stop
WestJet Logo
3:30 pm - 9:05 pm
YHZ
-
MKE
7h 35m
1 stop
$369WestJet
Fri, May 29 - Tue, Jun 2
American Airlines Logo
7:30 am - 11:24 pm
MKE
-
YYZ
14h 54m
1 stop
American Airlines Logo
11:39 am - 6:15 pm
YYZ
-
MKE
7h 36m
1 stop
$438American Airlines
Sat, May 23 - Wed, May 27
American Airlines Logo
8:12 am - 11:43 pm
MKE
-
YYC
16h 31m
1 stop
American Airlines Logo
1:40 pm - 7:42 am
YYC
-
MKE
17h 02m
1 stop
$438American Airlines
Wed, Jun 3 - Tue, Jun 9
Alaska Airlines Logo
4:40 pm - 8:53 pm
MKE
-
YVR
6h 13m
1 stop
Alaska Airlines Logo
11:50 am - 11:59 pm
YVR
-
MKE
10h 09m
1 stop
$492Alaska Airlines
Wed, Jun 3 - Tue, Jun 9
Alaska Airlines Logo
4:40 pm - 8:53 pm
MKE
-
YVR
6h 13m
1 stop
Alaska Airlines Logo
11:50 am - 11:59 pm
YVR
-
MKE
10h 09m
1 stop
$493Alaska Airlines
Wed, Jul 15 - Sun, Jul 19
United Airlines Logo
1:30 pm - 9:35 pm
MKE
-
YOW
7h 05m
1 stop
United Airlines Logo
6:05 am - 10:09 am
YOW
-
MKE
5h 04m
1 stop
$529United Airlines
Wed, Jul 15 - Sun, Jul 19
United Airlines Logo
10:39 am - 6:48 pm
MKE
-
YOW
7h 09m
2 stops
United Airlines Logo
6:05 am - 10:09 am
YOW
-
MKE
5h 04m
1 stop
$539United Airlines
Sun, Aug 2 - Thu, Aug 6
Delta Logo
9:39 am - 6:00 pm
MKE
-
YLW
10h 21m
2 stops
Delta Logo
6:05 am - 6:00 pm
YLW
-
MKE
9h 55m
2 stops
$629Delta
Mon, Aug 3 - Fri, Aug 7
Delta Logo
12:07 pm - 11:30 pm
MKE
-
YLW
13h 23m
2 stops
Delta Logo
6:05 am - 8:20 pm
YLW
-
MKE
12h 15m
2 stops
$666Delta
Booking Insights

KAYAK's insights & trends for Milwaukee to Canada flights

Get data-powered insights and trends into flights from Milwaukee to Canada to help you find the cheapest flights, the best time to fly and much more.

Which airlines fly non-stop between Milwaukee and Canada?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Milwaukee to Canada.

There are 2 airlines that fly nonstop from Milwaukee to Canada. They are Delta and WestJet. The cheapest airline for this route is WestJet, with the best round-trip deal found costing $191 and arriving in Calgary (YYC). On average, WestJet offers the best prices for nonstop flights between Milwaukee and Canada.

Which airlines provide the cheapest flights from Milwaukee to Canada?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Milwaukee to Canada were found on WestJet ($368) and American Airlines ($468).

Good to know

Low seasonFebruary
Cheapest flight$171
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Milwaukee to Halifax

FAQs - booking Canada flights

  • How does KAYAK find such low prices on flights from Milwaukee to Canada?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Milwaukee to Canada.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Milwaukee to Canada?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee to Canada is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Milwaukee to Canada?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Milwaukee to Canada with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Milwaukee to Canada?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Milwaukee to Canada up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Milwaukee to Canada

 
Need help choosing which airline to fly with from Milwaukee to Canada? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
Alaska AirlinesOverall score based on 12264 reviews
7.0Entertainment
7.8Comfort
8.1Boarding
8.5Crew
7.0Food
Airline reviews

See what I wrote in the previous section. This was a terrible experience. I would like refund.. I even paid an extra $70 for an aisle seat closer to the front to ensure that I got off early enough to catch the next flight. The fact that the plane did not wait, and even left eearlier, knowing that the first flight came in late, and was moved to a terminal three train stops away is appalling. My friend that flew JetBlue, their flight was delayed and came in later and the connecting flight WAITED for them. How is it that JetBlue could do that, and Alaska could not.

2.0 MediocreAnna, Apr 2026
SEA - LAX
Read more Alaska Airlines reviews

See what I wrote in the previous section. This was a terrible experience. I would like refund.. I even paid an extra $70 for an aisle seat closer to the front to ensure that I got off early enough to catch the next flight. The fact that the plane did not wait, and even left eearlier, knowing that the first flight came in late, and was moved to a terminal three train stops away is appalling. My friend that flew JetBlue, their flight was delayed and came in later and the connecting flight WAITED for them. How is it that JetBlue could do that, and Alaska could not.

Hello, Our flight arrived late, and the flight we were to connect to the departure time was moved up. At first our flight was scheduled to arrive at 10:40, but it arrived at 10:56. Our connecting flight was scheduled to leave at 11:25, and it was moved to 11:20. Also the terminal was moved from N to S. N would have been in the same terminal as the one we arrived in-- to get to S we had to take 3 trains to get to. And when we arrived at the gate, around 11:15, they said the gate was closed and would not open it. We had come from a funeral in Boston, and the person that helped us get new tickets said, "did you come from a girsl trip?" No, we did not. We were coming from a funeral. This experience was not what we expected/wanted. My friend, because she had to run to S, got a migraine and turned pale. In addition, I paid an extra $70 for an aisle seat that was more upfront, to make sure I can get off the plane faster and make the connecting flight. The fact that the plane not only did not wait, but left earlier, is absolutely unacceptable. This was a terrible experience, and I hope that I can be refunded for this horrible experience.

Had to buy a snack box as I am gluten free. They should be free in extra comfort. Food they provided was awful. Not enough water stops.

A gentleman at the desk for my boarding from Seattle to Anchorage randomly selected me and told me they would need to check my carry-on despite having multiple lithium-ion batteries all of which were in communication devices essential for time in Alaska. There was ample overhead compartment space and I was lucky non of my equipment was damaged due to his unnecessary use of power. A quick check with the flight crew would have likely resulted in an answer that ample space remained allowing me to keep my personal and important items near by. I did lose WiFi twice and that detracted from my entertainment which I do not commonly use.

The seat on the plane out was broken and would not lean back. I have back problems and sitting up straight was hard on my lower back and caused pain for over half the flight. Since I paid extra for First Class so I would not have these issues. This needs to be addressed.

The TSA pre check with photo linked to Alaskan airlines was extremely fast & convenient.

Flight was cancelled which destroyed the rest of our journey.

Tight hot cramped seating. Gate change plus a board and de plane request with two hour delay

Overall, it was a good flight. My only quip- they made us check our carry on bags when there was plenty of overhead space left. My wife and I thought maybe the aircraft was really full, but that wasn’t the case. There were a number of open seats, and even more overhead compartments with no luggage. A minor annoyance, sure, but when we intentionally didn’t check luggage to make it easier, it was disappointing to have to do it anyways.

We treated ourselves to first class and were underwhelmed by the experience. No screen for entertainment. Food was not great...only one or two options, small portions, dry. We won't waste our money upgrading again. Good news was we made it to PDX safe and sound. Crew was attentive.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

Didn't like sitting on the waiting pad for 30 minutes right after departing the gate. If you're going to do that, just don't board so people can still get up and walk around in the terminal. My luggage was damaged by the baggage handlers.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

The flight was way too HOT! And the plane did not have any in-flight TV entertainment.

Putting people that close to the bathroom, where you have to look into the bathroom as people are exiting and entering was not great and the smell was also not great. I know the airlines are desperate for more chairs, but that seat is a crime.

one staffer was frustrated (it happen); the flight was late and the pilot mentioned they'll make amend but the snacks were the same, other than that the aircraft was clean and everything went smooth, no complaints

ticket agent lady wás very helpful , she arranged wheel chair for my elderly mother

Entertainment kept turning itself off. Gave up on watching a movie.

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

Not United Airlines' fault. It's ORL airport's fault.

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

No pre boarding kiosk to check in, baggage claim detected luggage didn’t leave the airport, poorly managed recovery of lost luggage, and blame lost tag from conveyor to TSA/security, very poor from TSA/security check to delivery, crucial if compensation will go thru and will likely wait for months unlike United,

Flight was good, crew was excellent. No complaints at all

Delayed 3 times in a row for 4 hours total. Incrementally pushing back the flight claiming gate delays but they eventually changed the actual plane, due to technical issues. This strategy to avoid compensation to passengers is unprofessional.

Plane seating was uncomfortable, very tight fitting for someone my height, did not recline and overall un enjoyable

Everything was good except for flight delay, but it was because of the snow storm in the arrival airport.

No communication from Kayak or West Jet. Booked extra flights, flights cancelled, no one answers calls. Will be disputing charges.

The trip from LAX to Calgary was aboard a 737-700, which is more than twenty years old. Service was fine, and the food was good, but there was no inflight entertainment, and no WiFi. The flight from Calgary to Vancouver was also delayed more than an hour, due to congestion on the Calgary tarmac. And no food service, but there was in-flight WiFi which made a big difference.

Leg room is a problem the plane was dirty and there were no movies available on the app

The personal item sizer cannot take a standard backpack, and the cabin luggage sizer cannot take a standard carry-on. Designed for people from the island of Lilliput!!. and also compels people to pay additional fees to check their bags. Making money by ticking off the passengers is a very short-sighted business strategy, especially since they have a choice of carriers

my wife got very sick and we did not travel . we booked and bought the travel insurance and dot nothing but hassle and a triangle of stress in trying to make the insurance claim I called in and was told they would not give me anything in writing to say they would not refund my money back this make it impossible to file the claim I will never book with Kayak again.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

It was really a terrific experience both going and returning on AA. Staff and crew were professional.

The business class layout of chairs was weired. You are sitting directly across stranger.,

Flights on time w/o delays. However, my baggage was damaged. Ground crew, throws baggage from plane to the baggage carrier, carelessly.

I’m sure Business Class would be excellent. I feel like I got what I paid for. Overall it was good and well worth it. I would do it again.

I am writing to share detailed feedback regarding my recent journey with American Airlines on the New York (JFK) to New Delhi (DEL) sector, which was ultimately diverted to Jaipur (JAI) due to weather conditions. At the outset, I would like to acknowledge that this was a full long-haul flight of approximately 14–15 hours, and while the journey fulfilled its primary transport objective, several aspects of the experience warrant both recognition and constructive feedback. 1. Cabin Crew Conduct and Service Consistency While the majority of the cabin crew maintained a polite and professional demeanor, one flight attendant’s conduct was notably inconsistent with expected service standards. The tone was often directive and lacked the warmth and guest-centric engagement typically associated with long-haul service. This created a perceptible imbalance in the cabin experience. Although other crew members acknowledged and apologized for the behavior, it highlighted a gap in service standardization and supervisory oversight. 2. Inflight Experience (IFE & Comfort) The inflight entertainment system was unreliable, with content failing to load consistently throughout the journey. Seating comfort in economy class was below expectations when compared with other international long-haul carriers. Cabin environment management at times felt unsettled, with noticeable noise and movement in the aisles. 3. Disruption Handling and Communication (DEL Diversion to JAI) The diversion to Jaipur due to weather was understandably beyond the airline’s control. However, the handling of post-diversion communication and guest management was an area of concern: Information during and after the diversion was fragmented and lacked clarity Limited guidance was provided upon disembarkation regarding next steps (transport, accommodation, onward travel) Ground coordination appeared inconsistent, with hotel partners and passengers receiving incomplete or delayed updates Communication the following morning remained unclear, including last-minute changes to transfer timings This resulted in avoidable uncertainty during a critical disruption phase. 4. Positive Acknowledgment – Ground Recovery Arrangements It is important to recognize that despite the initial communication gaps, the overall recovery framework was eventually well executed: Hotel accommodation was arranged efficiently Meal vouchers were provided appropriately Transfers between airport and hotel were organized in a structured manner Given the sudden and large-scale disruption, these arrangements were commendable and reflect the airline’s ability to operationally recover once systems were in place. 5. Recommendations for Improvement In the interest of strengthening the overall customer experience, I would respectfully propose the following: Service Delivery Reinforce consistent cabin crew service standards, particularly for long-haul sectors Enhance supervisory presence to address outlier behaviors in real time Inflight Product Improve reliability of inflight entertainment systems Reassess economy seating comfort for ultra-long-haul routes Disruption Management Establish a more visible “Care & Coordination Team” during irregular operations Ensure clear, centralized communication (single source of truth) for passengers and ground partners Provide structured briefing points to hotel and transport vendors to avoid information gaps Introduce proactive guest engagement (clear next steps, timelines, reassurance) Closing Reflection: While the journey was impacted by both controllable and uncontrollable factors, the overall experience would have been significantly enhanced through greater consistency in service delivery and more structured communication during disruption. I appreciate the efforts made by the broader team in arranging accommodation and onward logistics under challenging circumstances. With improved coordination and alignment, the experience can be elevated to match the expectations of a global long-haul carrier. Thank you for your attention to this feedback. I trust it will be received constructively and contribute to ongoing service improvement. Warm regards, Soosnata Chowdhury Convert effective for airlines) Or tailor tone

This short sector between Miami and JFK was undertaken purely for business purposes, with efficiency as the primary objective rather than a full inflight experience. Overall, the journey met its intended purpose; however, the ground experience at Miami stood out significantly. During check-in, I was unable to link my frequent flyer details from Qatar Airways (oneworld alliance) through either the self-service kiosk or web check-in. The situation was handled exceptionally well by the check-in agent, who demonstrated remarkable ownership. She coordinated across multiple counters, ensured my frequent flyer number was correctly reflected, reissued the boarding pass, and confirmed that mileage accrual would be recognized. Additionally, she ensured the boarding pass reflected priority status, enabling a seamless priority check-in experience without delays. This level of proactive service was both commendable and impactful. Boarding and the inflight experience, operated by American Airlines under a codeshare arrangement, were efficient but largely transactional. While operational delivery was smooth, there was no visible recognition of oneworld frequent flyer status onboard. In comparison to the consistently personalized engagement typically experienced with Qatar Airways, this absence was noticeable—though understandably a potential limitation of codeshare alignment rather than a direct service shortfall. In summary, while the flight itself fulfilled its operational intent, the exceptional professionalism and commitment demonstrated at the Miami check-in counter was the defining highlight of this journey. Greater consistency in elite recognition across partner airlines would further enhance the overall experience.

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

Everything you need to know for your flight from Milwaukee to Canada

Information on your arrival and departure airports