Image Credits: Public Domain
Published March 11, 2026 by

Nonstop Flights: Chicago to/from Montego Bay, Jamaica $318-$343 round-trip [April-January] – United

[03/11/2026 @ 12:22 PM CT] Deal time-stamp.
[2026-04-13 07:09:00] 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).

This website contains cookies and links to companies that may compensate this site when you click on their links or ads. To view our ad disclosure and privacy policy, visit this page (link).

To book: Use our updated link list.

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

United has round-trip flights from Chicago (ORD) to Montego Bay, Jamaica (MBJ) for $318-$343, NONSTOP. Flights April to January. Very few weekends available. Origin/Destination reversible.

United’s “Basic Economy” fares do not allow for a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding.

The personal item size on United is smaller (9 x 10 x 17 inches) than Frontier or Spirit (8 x 13 x 18 inches).

If you use the United℠ Explorer Card, your first standard checked-bag for you and your companion is free, you get priority boarding, two United Club passes per year, and you get a 25% discount on inflight purchases on United-operated flights as a statement credit.

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.


Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

All our deal notifications are available for FREE via Instagram, Bluesky, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. Don’t pay anyone for a copy of our free blog posts.

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

Montego Bay fares: [2026-04-13 07:09:00] 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.


Our Affiliate Links:

This site receives referral credit when you use links on our page to open our affiliate’s page. By using our affiliate links when you begin your airfare or hotel search, you are supporting this site. Thanks.

Flights departing from a different city:

Other Useful Links:

  • [Budget Travel] – list all the posts that deal with Budget Travel (filter out all the flight deal posts)

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 Star Alliance United