Image Credits: Breezy Baldwin, Creative Commons 2.0
Published August 10, 2026 by

Cheap Flights: Milwaukee to/from San Juan, Puerto Rico $238-$243 round-trip (No Thanksgiving) – American Airlines

[08/10/2026 @ 12:28 PM CT] Deal time-stamp.

To book: Use our updated link list.

Or book with these sites: Expedia, Skyscanner, Priceline, Booking.com, Travelocity, Orbitz, CheapTickets, Kayak.

American Airlines has round-trip flights from Milwaukee (MKE) to San Juan, Puerto Rico (SJU) for $238-$243 with a connection. Flights August, September, October, November, January, and February. No Thursday departures. Origin/Destination reversible. No Thanksgiving dates.

American allows one carry-on bag and one personal item for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

If you use the Citi® / AAdvantage® Platinum Select® World Elite Mastercard® with AA flights, you get: a 25% inflight food and beverage discount, a $125 AA flight discount after you spend $20,000 or more in purchases during your card year, and your first checked bag is free on domestic American Airlines flights for you and up to four companions traveling on the same reservation.

You can usually save more money by booking your flight+hotel together as a package instead of separately.

We post new flight deals often! You can check out our other deals by returning to the Front Page of our website: escape.flights (linked).

Here are some other offers that we think are worth mentioning. List updated 04/21/2026.

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Use the example date links on our website to pull up the fare.

San Juan, Puerto Rico fares: [2026-08-14 10:56:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

When you are ready to book your flight or hotel, please use the links on our site to begin your booking process so we receive credit for the referral.

  • Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on Expedia, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.


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Ren P. Artemio

Ren P. Artemio

Ren is the Chief Director of Nap Times at Escape Houston, Escape ATX, Cheap DFW, and Escape Flights. He really likes researching airfare and the travel industry, especially when it means getting a cheap flight to anywhere (he's not picky).

Airfare Deals American Airlines Flights from Chicago / Milwaukee Flights from Milwaukee Oneworld Puerto Rico San Juan