Flight
We have flown into Ft. Lauderdale airport, rented a car, and made the scenic 3 hour drive down the Overseas Highway! Not only is it beautiful, but it is also much cheaper to do it that way than flying straight into Key West. If you want to forgo the drive down, they have the Key West International Airport as another option to fly into!
Hotel
We have stayed here and highly recommend it not only for the decent nightly rates but their guest service is amazing! They have a free shuttle that takes you directly to Duval Street for free and runs every half hour so no need to drink and drive after partying at the bars on Duval!
Flight
American Airlines & United offer direct flights from Chicago O’Hare and one stop flights from the West coast. Delta is also an option into Key West but does not offer non-stop flights. A perk is that you do not need to rent a car if you fly into Key West.