$108 Find Cheap Flights from Key West to Chicago - Compare and Save

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

• Earliest: departs at 9:00 am and lands at 12:51 pm
• Latest: departs at 6:35 pm and lands at 10:26 pm.

The flight takes about 3h 51m.

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

• Economy Class
• First Class

A nonstop flight from Key West to Chicago takes 3h 51m, 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 Key West to Chicago range from $323 to $429, with an average of $372 over the past 12 months. Anything below $323 counts as a good deal.

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $349 round-trip, compared to $370 via a layover through Miami (MIA).

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.

Afternoon is the busiest departure period on Key West to Chicago flights, with 66% of flights leaving in that window. Evening departures account for 33%, morning flights for 1%, 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 $225 to $2,077. That means the highest observed fare was about 9x higher than the lowest one.

One-way fares from Key West to Chicago are currently lower than usual. Average one-way flight prices are about $136, which is 57% below the typical average for this route.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Dollar
• Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

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

Connecting flights from Key West to Chicago most commonly pass through:

• Atlanta Hartsfield-Jackson (ATL) - 83% of one-stop connections
• Miami (MIA) - 17% of one-stop connections

Yes. Flexible dates can save you up to 39% on flights from Key West to Chicago. Friday is the cheapest departure day at $268 round-trip on average, while Saturday is the most expensive at $434, a difference of $166.

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

• United Airlines
• American Airlines

Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 5h 25m, compared with 6h 42m via Miami (MIA).

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

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

Among airlines operating Key West to Chicago flights:

• American Airlines: offers extra legroom; offers free seat selection
• United Airlines: 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 in Economy Class class

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