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Selected fares from Chicago to Key West
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Route Information for Flights from Chicago to Key West
| Origin Airport IATA Code | MDW |
|---|---|
| Destination Airport IATA Code | EYW |
| Flight Price | $218 |
| Distance | 1,982 km |
Chicago (CHI) to Key West (EYW)
Whether you're traveling for business or pleasure, you're going to want a great deal on a flight to Key West. Because when you land, you have a city that is waiting to be explored, and that extra cash in your pocket can take your trip from "meh" to amazing. You're in the right spot to snatch an awesome deal on your next flight from Chicago. Whether you are an expert at navigating the friendly skies or aerial amateur, read below to score the best deal on your next flight.
How do you get the best deal on a ticket from CHI to EYW?
Hotwire has been in the game a long time, so we know a few ways to get the best deal on your flight to Key West. You can pocket that extra cash for more than just getting from point A to point B with a little know-how.
What is the best day of the week to book a flight?
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.
What's the Saturday night stay rule?
If you stay through the weekend, generally that return ticket to CHI can be cheaper since you'll be leaving earlier in the week. All those business travelers have less flexible schedules, so that means savings for you. Good thing to tell your boss if you have a business trip -- wink-wink.
Why travel during the off-peak season?
It's all about going to a place when its weather is at its best. For example, Europe, Hawaii, and Alaska are big hits in the summer. Popular Spring Break destinations are New Orleans, California, and Florida. Feeling the bitter cold? Well, the Caribbean Islands and Mexico can warm you up. Unless you're a ski bum -- then places like Colorado will be your winter wonderland. Who doesn't love that harvest of autumn colors? The Pacific Northwest, Northern California, and New England are popular this time of the year. Flying during the off-peak seasons to certain locations can mean extra money in your wallet -- yes, please!
Is that the lowest price?
Airlines change their rates frequently. If a price you like pops up, then pick it. Unsurprisingly, you're not the only vacation-hungry person seeking an awesome price on a flight from Chicago to Key West. You might miss your opportunity to dial in the time and the flight you wanted.
Are there any other ways to save on my flight to Key West?
The Hotwire Hot Rate is what makes us stand out from the rest. You'll get one of our best rates on your flight from Chicago (CHI) to Key West (EYW). You won't know the time and airline until after you book, but it is a risk where you can reap the rewards.
Book your flight today
At Hotwire we'll do our best to help you save on your ticket to Key West. These tips can help you score that unreal deal. For thrill seekers, go for the Hotwire Hot Rate. You'll get your flight and have more cash in your pocket to do Key West up right. So say "So long" to Chicago and "What's up?" to Key West.
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^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.