Flights from Chicago (MDW) to Key West (EYW)
Change your flight without a fee on select flights
Money Saving Bundle when you purchase Hotel + Flight!
Get mobile alerts about flight delays, gate changes and more with the FREE Wotif app
Chicago to Key West Flight Information
Find the Cheapest Flights from Chicago (MDW) to Key West (EYW)
Work hard, travel harder! Wotif brings you the cheapest Chicago to Key West flights, making it possible to have a five star holiday without that five star price tag. Browse and compare our top MDW to EYW routes and airport options. So, go ahead and treat yourself, your sweetheart, or the kids to an unforgettable holiday this year.
to Information
Traveling From | Midway Intl. |
|---|---|
Origin Airport | |
Origin Airport IATA Code | MDW |
Traveling To | Key West Intl. |
Destination Airport | |
Destination Airport IATA Code | EYW |
Number of Airlines Serving | |
Average Flight Time | hours mins |
Direct Flight Time | hours mins |
Flight Price |
Chicago to Key West Flight Deals from
Considering a quick trip to Key West, but not sure which is the best route for you? Well, you’re in luck! Wotif has done the hard work, so all you need to do is check out these flights from MDW to EYW. With heaps of cheap fares from Chicago, we guarantee you’ll be arriving to your holiday destination in style without emptying your bank account in the process.
It’s easy to book flights to Key West from Chicago
For a huge choice of flights, simply enter your travel dates and hit search and we’ll hunt out fantastic deals on one-way, return and multi-city airfares to Key West from Chicago from different airlines. If you click the ‘direct flights’ box, you see flights that’ll get you to Key West in just hour(s) and mins, too.
Snap up great deals on flights to Key West from Chicago
Choose from flights a day on average, with prices starting at and rising to depending on the cabin class, travel dates, and airline carrier. And if you’re up for a last-minute getaway, you can get great deals on flights from Chicago to Key West today!
Find cheap airfares to Key West from Chicago
Here are our insider tips for bagging a flight bargain:
- Look for midweek flights and late night, early morning arrival and departure times
- Check out other airports near Chicago and Key West
- Avoid peak season (prices tend to be lower in )
- Be flexible with your travel dates and you can usually get cheaper options
Reasons to book your flights to Key West from Chicago with Wotif
Wotif is a super-easy way to find the best flight for you to Key West. Get more bang for your buck on flight and hotel or car rental combos and download the free Wotif app to tap into exclusive deals. Book now with Wotif and have a great flight!
Great places to stay after flight from Chicago to Key West
Reviewed on 27 May 2025
Reviewed on 22 May 2025
Reviewed on 22 May 2025
Discover top hotels, vacation package, cheap car rental deals and more with Wotif!
Other Flight Destinations
^Savings based on all package bookings made with Flight + Hotel on Wotif.co.nz from , 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.