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Published April 21, 2026 by

Nonstop Flights: Chicago to/from Montego Bay, Jamaica $318-$328 round-trip [April-March] – Southwest

[04/21/2026 @ 11:39 AM CT] Deal time-stamp.
[2026-05-24 07:44:00] 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.

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

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Southwest has round-trip flights from Chicago (MDW) to Montego Bay, Jamaica (MBJ) for $318-$328, NONSTOP. Flights April to March. Weekends available. Origin/Destination reversible.

Use a card like the Southwest Rapid Rewards® Plus Credit Card to earn points towards a Companion Pass®. Companion Pass is the benefit that allows you to choose one person to fly with you, free of airline charges* every time you purchase or redeem points for a flight. *Companion Pass doesn’t cover taxes and fees.

It is common to find Southwest gift-cards for sale at a discount of about -$70 to -$20 off the redeemable value at Costco and Sam’s Club. Before you finalize your booking you should check to see if you can save more money by using a gift card.

Southwest Vacations usually has discounted package deals available that can save you more money. Package deals require than you book your flight + hotel together as a package, so it’s less flexible, but the package discount may be significantly cheaper than booking your flight and hotel separately.

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 04/21/2026.

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.

Montego Bay fares: [2026-05-24 07:44:00] 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: 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 Flights from Chicago / Milwaukee Montego Bay Southwest