Cheap Flights: Chicago to/from Grand Cayman $316-$328 r/t [mid-August] – Southwest

[04/25/2022 @ 08:05 PM] Book this fare on: Southwest, (Other Airlines: Priceline, Travelocity, Tripadvisor, Skyscanner, Expedia, Orbitz, Hotwire, CheapTickets.)

Other airlines may begin matching this fare. Before you commit to purchase, you may want to do a quick check on BookingBuddy to see if another airline offers better routing or a better deal.

The details on this page were accurate when this post was last updated (see time-stamp). Deals are usually valid 24 to 72 hours after posting, but can expire at any time. This website contains cookies for personalized ads and links to companies that may compensate this site when you click on their link. By continuing to use this website, you consent to the use of ads, affiliate links, and cookies.

Southwest has round-trip flights from Chicago (MDW) to Grand Cayman (GCM) for $316-$328, with one or two connection. Flights mid-August to late-August. Origin/Destination reversible.

Note: On some dates, there are two connections on the return flight. Try other nearby dates to see if better routing exists before finalizing your trip.

Southwest doesn’t charge a fee for changes, cancellations, or carry-on bags.

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

Patreon supporters receive a recap of all the airfare deals currently available everyday.

We don’t charge a subscription fee. Our deal notifications are available for FREE via Instagram, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

I was able to pull this up on Southwest. Screenshot taken when this post was initially created. See timestamps at the top of this post.

Note: OTAs such as Travelocity and Priceline allow free cancellation without penalty within 24-hours after you purchase. As deals sell-out or expire quickly, this policy will allow you to “lock-in” the cheap fare while you sort out a plan. Just keep in mind that after 24-hours, you will not be able to cancel without the regular penalty.

Coupon Codes:




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)