Delta has round-trip flights from Chicago (MDW) to Key West (EYW) for $177 with a connection. Flights April, May, July, August, September, October, November, and December. No Thursday departures. Origin/Destination reversible. Holiday blackouts.
Category: <span>Key West</span>
Image Credits: Evangelio Gonzalez
Image Credits: Evangelio Gonzalez
United and American Airlines have round-trip flights from Chicago (ORD) to Key West (EYW) for $189-$232, NONSTOP. Flights October to January. No Thursday departures. Extended weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Image Credits: Evangelio Gonzalez
United and American Airlines have round-trip flights from Chicago (ORD) to Key West (EYW) for $139-$158, NONSTOP or with connections. Flights September to November. No Friday departures. Very few extended weekends available. Origin/Destination reversible. No Thanksgiving dates.
Dates are scattered: Most dates are clustered around the start of September, the end of October, and the start of November.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Image Credits: Evangelio Gonzalez
United has round-trip flights from Newark/New York (EWR) to Key West (EYW) for $179-$194, NONSTOP. Flights August to September. Extended weekends available. Origin/Destination reversible.
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.
Image Credits: Evangelio Gonzalez
American Airlines has round-trip flights from Chicago (ORD) to Key West (EYW) for $196-$229 with a connection. Flights April to July. Extended weekends available. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Image Credits: Evangelio Gonzalez
American Airlines has round-trip flights from New York (LGA) to Key West (EYW) for $177-$207, NONSTOP. Flights March to May. Departures on Monday, Tuesday, Wednesday, Saturday, and Sunday. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Image Credits: Evangelio Gonzalez
American Airlines has round-trip flights from Chicago (ORD) to Key West (EYW) for $208-$228, NONSTOP. Flights October to February. No Saturday departures. Extended weekends available.
Image Credits: Evangelio Gonzalez
United has round-trip flights from Newark/New York (EWR) to Key West (EYW) for $188-$218, NONSTOP or with a connection. Flights in April, October, and January. Extended weekends available. Limited availability.
Image Credits: Evangelio Gonzalez
American Airlines has round-trip flights from Chicago (ORD) to Key West (EYW) for $178-$208, NONSTOP or with connections. Flights in April, August, September, October, November, and December. Extended weekends available. Origin/Destination reversible. Holiday blackouts.
Nonstop fares are limited and only in December.
Image Credits: Evangelio Gonzalez
American Airlines has round-trip flights from Chicago (ORD) to Key West (EYW) for $224-$227 with a connection. Flights April to October. Extended weekends available.
Image Credits: Evangelio Gonzalez
United has round-trip flights from Newark/New York (EWR) to Key West (EYW) for $168, NONSTOP. Flights November to February. Extended weekends available. Holiday blackouts.
Image Credits: Evangelio Gonzalez
American Airlines has round-trip flights from Chicago (ORD) to Key West (EYW) for $208, NONSTOP. Flights January to March. No Saturday departures. Extended weekends available.
Nonstop Flights: Chicago to Key West $228-$256 r/t [September-November] – American Airlines / United
Image Credits: Evangelio Gonzalez
Nonstop Flights: Chicago to Key West $228-$256 r/t [September-November] – American Airlines / United
American Airlines and United have round-trip flights from Chicago (ORD) to Key West (EYW) for $228-$256, NONSTOP. Flights September to November. No Sunday departures. Very few weekends available.
Image Credits: Evangelio Gonzalez
American Airlines and Delta have round-trip flights from Denver (DEN) to Key West (EYW) for $233-$250 with a connection. Flights April, May, August, September, October, and December. No Thursday departures. Mostly midweek, weekdays. Origin/Destination reversible.
Image Credits: Evangelio Gonzalez
American Airlines and Delta have round-trip flights from Denver (DEN) to Key West (EYW) for $223-$226 with a connection. Flights February to November. Extended weekends available.
Image Credits: Evangelio Gonzalez
JetBlue has round-trip flights from New York (JFK) to Key West (EYW) for $137, NONSTOP. Flights October, November, January, February, March, April, and July. Departures on Monday, Tuesday, Wednesday, Thursday, and Sunday. No Fridays or Saturdays. Very few extended weekends available.
Image Credits: Dori, Creative Commons 3.0
Delta has round-trip flights from Milwaukee (MKE) to Key West (EYW) for $239 with a connection. Flights August to October. Very few weekends available.
Image Credits: Evangelio Gonzalez
JetBlue and United have round-trip flights from New York (JFK/LGA) to Key West (EYW) for $137-$147, NONSTOP. Flights August to September. Very few weekends available. Origin/Destination reversible.
Image Credits: Evangelio Gonzalez
American Airlines and Delta have round-trip flights from Phoenix (PHX) to Key West (EYW) for $234-$237 with a connection. Flights August to October. Extended weekends available.
Image Credits: Evangelio Gonzalez
American Airlines and Delta have round-trip flights from Milwaukee (MKE) to Key West (EYW) for $214-$217 with a connection. Flights in July and September to October. No Thursday departures.