Cheap Flights from Chicago (CHI) to Grand Cayman (GCM)

Chicago (CHI) to Grand Cayman (GCM)

What?! A trip to Grand Cayman! Well, looks like you'll need a flight from Chicago pretty soon. Well, unless you'd rather walk. And although we agree walking is great exercise, you probably want to get there before the year ends. Fortunately, you found us. We can get you a fabulous rate on your flight from CHI to GCM.

How do you get the best deal on a ticket from Chicago to Grand Cayman?

We've been doing this for a long time, which means getting that great deal on a Grand Cayman flight is easy-peasy. You can pocket that extra cash for more than just getting from point A to point B with a little know-how.

Which days of the week are cheapest to fly?

With the right attitude and flexibility, you can fly for less. Below are the cheapest days to fly:

• Tuesday and Wednesday—You know how most stores are not crowded midweek? Same thing here. Most people opt to depart at the beginning or end of the week.
• Thursday and Saturday—Get a head start on that Friday crowd. This also works on your return flight. Shorten your vacay by a day and increase your savings.
• Monday through Thursday—If you're flying internationally, deals are often available when departing these days.

Can staying the weekend get me a cheaper ticket?

Staying the weekend at your destination, like Grand Cayman, usually means a more affordable return ticket since most people fly during this time. We are all for that!

Can you save while traveling during the off-peak season?

Off-peak and shoulder seasons are when most vacationers aren't going to certain locations. So when it's cold, most people head off to warmer places like the Caribbean, Mexico, Hawaii, etc., just like the birds (they had it figured out). But during the summer, you'll find that Europe is really popular. You can usually save on your ticket when you avoid flying during the peak seasons.

Is that the lowest price?

Airline carriers change their rates frequently. If a price you love pops up, then grab it. There are a lot of other people that are waiting a good price on a ticket from Chicago to Grand Cayman. You may miss out on your chance to get the flight and the time you need.

What is the Hotwire Hot Rate?

The Hotwire Hot Rate is for travelers who have a lot of flexibility in their travel plans. It's one of our ways to help get you one of the best rates on your flight from Chicago (CHI) to Grand Cayman (GCM). After your purchase, you'll get the time and name of the airline, but with a little risk you can get huge savings.

Book your flight today

At Hotwire we'll do our best to help you save on your next flight to Grand Cayman. Use our guide to get you that unreal rate. For the ultra-flexible-go with the flow vacationer, go for the Hotwire Hot Rate. You'll get your flight and have more money in your hand to do Grand Cayman up right. So say "Goodbye" to Chicago and "Hi" to Grand Cayman.

^Savings based on all package bookings with Flight + Hotel made on Hotwire.com from January 1, 2018 to December 31, 2018 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.