$112 Find Cheap Flights from Chicago to Key West - Compare and Save

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.

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.

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

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).

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 travelers should check the fare details before booking.

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

• Economy Class
• Premium Economy Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $230 round-trip via Orlando (MCO), compared to $451 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.

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

• Atlanta Hartsfield-Jackson (ATL) - 41% of one-stop connections
• Fort Lauderdale (FLL) - 22% of one-stop connections
• Miami (MIA) - 20% of one-stop connections
• Charlotte Douglas (CLT) - 14% of one-stop connections

Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 23% on the Chicago to Key West route. Tuesday is the cheapest departure day at $387 round-trip on average, while Sunday is the most expensive at $500, a difference of $113. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

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.

A nonstop flight from Chicago to Key West takes 3h 20m, covering 1,242 miles.

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

• Earliest: departs at 7:30 am and lands at 10:50 am
• Latest: departs at 12:10 pm and lands at 3:30 pm.

The flight takes about 3h 20m.

Last-minute fares on this route - booked within 2 weeks of departure - run 12% above the route average of $438. Book 10 weeks before departure for the lowest fares.

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.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $249 to $2,360. That means the highest observed fare was about 9x higher than the lowest one.

One-way fares from Chicago to Key West are currently lower than usual. Average one-way flight prices are about $162, which is 44% below the typical average for this route.

Flying via Miami (MIA) gives the shortest average 1-stop total travel time at 5h 24m, compared with 5h 31m via Atlanta Hartsfield-Jackson (ATL) and 6h 00m via Charlotte Douglas (CLT).

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.

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

Round-trip flights from Chicago to Key West range from $349 to $568, with an average of $438 over the past 12 months. Anything below $349 counts as a good deal.