$367 Find Cheap Flights from Jamaica to Milwaukee

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Milwaukee departing on 7/3. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Milwaukee

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Milwaukee, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Milwaukee, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Jamaica to Milwaukee

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jamaica to Milwaukee 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 Jamaica to Milwaukee

Thu, Jul 9 - Thu, Jul 16
American Airlines Logo
12:25 pm - 9:54 pm
MBJ
-
MKE
9h 29m
1 stop
American Airlines Logo
6:17 pm - 11:25 am
MKE
-
MBJ
17h 08m
1 stop
$526American Airlines
Thu, Jul 9 - Thu, Jul 16
American Airlines Logo
5:14 pm - 12:44 pm
MBJ
-
MKE
19h 30m
2 stops
American Airlines Logo
6:55 pm - 11:25 am
MKE
-
MBJ
16h 30m
2 stops
$531American Airlines
Fri, Jul 3 - Sat, Sep 5
United Airlines Logo
2:40 pm - 7:00 am
MBJ
-
MKE
16h 20m
2 stops
United Airlines Logo
11:18 am - 11:43 am
MKE
-
MBJ
24h 25m
2 stops
$533United Airlines
Fri, Jul 3 - Sat, Jul 4
Southwest Logo
12:35 pm - 7:30 pm
MBJ
-
MKE
6h 55m
1 stop
Southwest Logo
6:00 am - 2:00 pm
MKE
-
MBJ
8h 00m
1 stop
$571Southwest
Fri, Jul 3 - Sat, Sep 5
American Airlines Logo
12:25 pm - 9:54 pm
MBJ
-
MKE
9h 29m
1 stop
American Airlines Logo
6:48 pm - 1:34 pm
MKE
-
MBJ
18h 46m
2 stops
$599American Airlines
Fri, Jul 3 - Sat, Sep 5
American Airlines Logo
3:02 pm - 11:44 pm
MBJ
-
MKE
8h 42m
1 stop
American Airlines Logo
6:48 pm - 1:12 pm
MKE
-
MBJ
18h 24m
1 stop
$600American Airlines
Fri, Jul 3 - Sat, Jul 4
United Airlines Logo
4:12 pm - 2:36 pm
MBJ
-
MKE
22h 24m
2 stops
United Airlines Logo
5:29 pm - 1:30 pm
MKE
-
MBJ
20h 01m
2 stops
$859United Airlines
Mon, Aug 24 - Tue, Aug 25
United Airlines Logo
12:52 pm - 7:07 am
MBJ
-
MKE
18h 15m
2 stops
United Airlines Logo
11:48 am - 11:43 am
MKE
-
MBJ
23h 55m
2 stops
$951United Airlines
Mon, Aug 24 - Tue, Aug 25
United Airlines Logo
12:52 pm - 7:07 am
MBJ
-
MKE
18h 15m
2 stops
United Airlines Logo
11:45 am - 11:43 am
MKE
-
MBJ
23h 58m
1 stop
$964United Airlines
Mon, Aug 24 - Tue, Aug 25
United Airlines Logo
12:52 pm - 7:07 am
MBJ
-
MKE
18h 15m
2 stops
United Airlines Logo
11:45 am - 11:43 am
MKE
-
MBJ
23h 58m
1 stop
$1,046United Airlines
Booking Insights

KAYAK's insights & trends for flights to Milwaukee

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

What is the cheapest flight to Milwaukee?

These are the best round-trip prices found by users searching on KAYAK in the last 7 days.

In the last 7 days, the cheapest flight deal to Milwaukee was found on the route from Montego Bay, at $526 return. The most popular connection is from Boston to Milwaukee and KAYAK users have found round-trip deals for as low as $187 in the last 7 days.

Find deals

Good to know

Cheapest flight$367
Flight from Montego Bay to Milwaukee

FAQs - booking Milwaukee flights

  • What is the cheapest flight to Milwaukee?

    In the last 7 days, the cheapest flight deal to Milwaukee was found on the route from Montego Bay, at $526 return. The most popular connection is from Boston to Milwaukee and KAYAK users have found round-trip deals for as low as $187 in the last 7 days.

  • How far is Milwaukee-Mitchell Airport from central Milwaukee?

    There are 6 miles between Milwaukee city center and Milwaukee-Mitchell Airport.

  • What is the name of Milwaukee’s airport?

    All flights to Milwaukee land at Milwaukee-Mitchell Airport. The airport code is MKE,and it can also be referred to as General Mitchell Intl or Milwaukee-Mitchell.

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

    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 to Milwaukee.

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

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

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

    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 to Milwaukee 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 to Milwaukee?

    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 to Milwaukee up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many direct flights to Milwaukee are there each week?

    Each week there are around 1,712 direct flights from within Jamaica to Milwaukee. The most common day for departures is Sunday, with 17% of flights taking off on this day.

Top tips for finding cheap flights to Milwaukee

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Milwaukee flight deals.

Reviews of the top airline flying from Jamaica to Milwaukee

 
See real verified KAYAK customer reviews for airlines flying to Milwaukee. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Jamaica to Milwaukee. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Milwaukee? 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.
7.1
American AirlinesOverall score based on 11642 reviews
6.9Entertainment
7.9Crew
6.4Food
7.2Comfort
7.5Boarding
Airline reviews

Was put into a seat right behind the toilet that had no entertainment possible but did have plenty of leg room over noisy part of plane.

6.0 GoodElizabeth, May 2026
DFW - SFO
Read more American Airlines reviews

Was put into a seat right behind the toilet that had no entertainment possible but did have plenty of leg room over noisy part of plane.

The passport line was so long that many of us were concerned about missing our flight and some did. It would've helped if a AA representative had gone to the passport check-in sooner to advise that boarding was closing and those flying that were stuck back in the line, needed to come forward with apologies to others. An AA representative did do that but only after boarding had already closed. (They delayed take-off so that more who were running with carry-ons could get to the gate - especially stressful for older people!) Then to be crammed into a seat with barely enough leg room for a thin woman, 5'7", like me, much less for a taller, bigger person was not comfortable, especially if the person in front decided to lean back. Crew was fine, food and entertainment also.

Movies on my phone are great. It would be nice to have a gluten free snack option.

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

The flight was peaceful, just s slight turbulence, pilots and crews were all nice and made a great job! Arrived safely in the Philippines. Thank you ya’ll!

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
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Everything you need to know for your flight to Milwaukee

Information on the airport you'll fly into in Milwaukee

Milwaukee (MKE)