$116 Find Cheap Flights from Chicago to Key West - Compare and Save

These are the earliest and latest flight times available from Chicago to Key West:

• Earliest: departs at 7:00 am and lands at 10:32 am
• Latest: departs at 12:30 pm and lands at 4:02 pm.

The flight takes about 3h 32m.

Two cabin classes are available on flights from Chicago to Key West:

• Economy Class
• First Class

A nonstop flight from Chicago to Key West takes 3h 32m, covering 1,242 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

Round-trip flights from Chicago to Key West range from $349 to $569, with an average of $433 over the past 12 months. Anything below $349 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 13% above the $433 route average. Book 10 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $230 round-trip via Orlando (MCO), compared to $449 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Morning is the busiest departure period on Chicago to Key West flights, with 67% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 0%, and night flights for 0%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $259 to $2,355. That means the highest observed fare was about 9x higher than the lowest one.

American Airlines is the only airline on the Chicago to Key West route offering in-flight Wi-Fi. Pricing depends on fare class.

One-way fares from Chicago to Key West are currently lower than usual. Average one-way flight prices are about $228, which is 23% below the typical average for this route.

Key West Airport (EYW) hosts 5 major car rental companies, with daily rates starting from around $29 for economy cars. Top options include:

• Dollar
• Hertz
• Budget
• Enterprise Rent-A-Car
• Alamo

Flights from Chicago to Key West may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Key West (EYW).

One-stop flights from Chicago to Key West most commonly connect through:

• Atlanta Hartsfield-Jackson (ATL) - 33% of one-stop connections
• Miami (MIA) - 25% of one-stop connections
• Fort Lauderdale (FLL) - 24% of one-stop connections
• Charlotte Douglas (CLT) - 15% of one-stop connections

Yes. Flexible dates can save you up to 25% on flights from Chicago to Key West. Tuesday is the cheapest departure day at $378 round-trip on average, while Sunday is the most expensive at $500, a difference of $122.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

2 airlines operate flights between Chicago and Key West. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines

Flying via Miami (MIA) gives the shortest average 1-stop total travel time at 5h 29m, compared with 5h 30m via Atlanta Hartsfield-Jackson (ATL) and 5h 56m via Chicago O'Hare Intl (ORD).

Key West is 1 hour ahead of Chicago (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Some of the most popular sights in Key West are Duval Street, Key West Historic District and Mallory Square. These are among the most viewed places in Key West on KAYAK.

Among airlines operating Chicago to Key West flights:

• American Airlines: offers extra legroom; offers free seat selection
• United Airlines: offers extra legroom; offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Here are some options for this route, based on selected ticket types and cabin classes:

• American Airlines: a cabin bag and a checked bag in Economy Class
• United Airlines: a cabin bag and a checked bag in Economy Class

Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Key West Airport has pet relief areas located at arrivals and departures. The designated relief areas in arrivals are outside the baggage claim, near the blue curbside for passenger pick-ups while those in departures are near the restrooms. You’ll find waste bags and trash containers which visitors can use to clean after their pets.

Renting a car is sometimes more convenient than taking a taxi. Some rental car companies at Key Stone Airport are Hertz, Avis, Budget, and Dollar. Once you land at the airport and are looking to rent a car, head to the car rental counters in the arrivals baggage claim area.

USO military lounges provide a space for military personnel and their family members to sit, relax and wait for their flight. Chicago Midway Airport has a USO military lounge located at concourse C post-security. The lounge features free internet, complimentary food and beverages, reading materials, and a TV for entertainment.

Chicago O'Hare has unique services for passengers who need guidance, support, and advocacy. Travelers Aid Chicago social service in terminal 2 of O'Hare Airport provides social assistance for travelers and visitors and crisis intervention information.