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Published January 21, 2026 by

Nonstop Flights: Chicago to San Jose, Costa Rica or Montego Bay, Jamaica $301-$361 round-trip [Feb-Mar / Feb-May] – American Airlines

[01/21/2026 @ 03:31 PM CT] Deal time-stamp.
[2026-02-14 08:14:00] Fare is still available. Only a few valid dates remain. Example dates have been updated.

Deals are usually valid 24 to 72 hours after posting, but can expire at any time (see time-stamp).

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To book: Use our updated link list.

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

American Airlines has round-trip flights from Chicago (ORD) to San Jose, Costa Rica or Montego Bay, Jamaica (SJO, MBJ) for $301-$361, NONSTOP.

  • San Jose: Flights February to March.
  • Montego Bay: Flights February to May.

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.

Do a search on Tripadvisor to find guides, tours, restaurants, attractions, and cool things to do. It’s a good resource to use for planning your day-to-day itinerary while on vacation.

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 01/21/2026.

We now track coupon codes, discount codes, gift card discounts, and credit card offers that have a better value than their historical averages.


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

San Jose, Costa Rica fares: [2026-02-14 08:14:00] Fare is still available. Only a few valid dates remain. Example dates have been updated.

Montego Bay fares: [2026-02-14 08:46:00] This fare is still available, but the original date ranges may have shifted. We have updated the example date links in this post to reflect those changes. Expect prices to fluctuate by about +/- 10%.

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: The Chase Sapphire Preferred® Card allows for 1-to-1 point transfers to several airline loyalty programs. Booking with points is a good alternative to paying with cash when the price of airfare is high. Here is the current list of Chase Sapphire transfer partners: United, Southwest, jetBlue, British Airways, Iberia, Singapore Airlines, Emirates, Air France, KLM, Virgin Atlantic, Aer Lingus, and Air Canada.
  • Tips: Use Tripadvisor to create a Hotel “short list”. First, plug in your dates and destination. Then select “Sort by Traveler Ranked”. Finally, select the “Traveler Ranking” filter to show “only 4* and up”. Use this resulting “short list” of hotels to find the cheapest one with a high ranking.
  • Tips: Hotel rates for Weekend dates are usually higher than the rates for Sunday through Thursday. Tripadvisor has a color-coded date calendar, red when the average hotel price for that day is more expensive, green for less expensive. You can use this to get an overview of what dates in the month are at a discount.
  • Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on BookingBuddy, 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 Costa Rica Flights from Chicago / Milwaukee Oneworld San Jose