Image Credits: Barry Peters, Creative Commons 2.0
Published June 9, 2023 by

Nonstop Flights: Chicago to Grand Cayman $284-$384 r/t [Oct 29 – Nov 04] (Use $100 off coupon) (Very limited: Only available on those dates) – United

[06/08/2023 @ 08:06 PM CT] Deal time-stamp.
[2023-06-09 10:00:00] 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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To book: Use our updated link list.
Or book with these sites: Hopper, Expedia, Priceline, BookingBuddy, Travelocity, Tripadvisor, Skyscanner, Orbitz, Hotwire, CheapTickets, Kayak.

Hopper has a $100 off Cayman Islands coupon.

United has round-trip flights from Chicago (ORD) to Grand Cayman (GCM) for $384, NONSTOP. If you apply the Hopper coupon, the cost of the round-trip is about $284. Flights in October. Departures on Sunday.

This deal is very limited, it’s only available as a round-trip departing Oct 29, returning Nov 04, but at this price I think it is worth it to whomever picks it up.

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.

These types of Hopper sales are common. They usually release new coupons every month. If you manage your notification settings on the Hopper app, you will never miss another Hopper flash sale.

Whenever Hopper has these kinds of sales, all you need to do to get a good deal is pair it with a quick Expedia or Google Search, select the lowest fare from there, and then plug those dates into the Hopper app with the coupon. We’ve linked the Expedia fares with the lowest dates for each destination on our website.

Keep in mind that Hopper is an OTA, so don’t expect them to have a free 24-hour cancellation period, or the lowest base fare price. Their customer service options are via “App only”, a negative for sure. Hopper will also try to up-sell you on a lot of extras like “cancel for any reason” policies that in our opinion, suck; decline all of those extras. Be sure to sort the search results by price, Hopper doesn’t do that automatically.

Here are some other offers that we think are worth mentioning. List updated 01/21/2026.

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

  • Chicago to Grand Cayman - Example Dates: (Expedia / Travelocity) Oct 29 - Nov 04 / Other dates: There may be more dates available than the ones we list here, use the "flexible date" button on Expedia to find similar fares.
  • Vacation rentals in Grand Cayman under $180 a night: (Vrbo) Oct 29 - Nov 04 / Note: There are more properties available outside of the $180 price filter. To see those, remove the filter on the VRBO search page.
  • Hotels in Grand Cayman under $300 a night: (Hotels.com) Oct 29 - Nov 04 / Note: There are more hotels available outside of the $300 price filter. To see those, remove the filter on the hotels.com search page.

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

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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Other Useful Links:

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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).

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