Rome2Rio

How to get fromChicago to Key Westby plane, bus (Flixbus, Greyhound), train, bus or car

Find Transport to Key West

See all options

There are 7 ways to get from Chicago to Key West by plane, bus (Flixbus, Greyhound), train, bus, or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly from Chicago O'Hare International Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Key West International Airport (EYW)plane plane ORD - EYW
    5h 9m
    $134–618

  2. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to Miami Airport Stationbus bus
    3. Take the bus from Miami Airport Station to Big Pine Keybus bus
    4. Take the bus from Big Pine Key - CVS / MM30 to N Roosevelt & 3rd Streetbus bus Lks
    39h 36m
    $154–436

  3. Train, bus

    1. Take the train from Chicago Union Station to Hollywood Amtrak Stationtrain train
    2. Take the bus from Miami Airport Station to Big Pine Keybus bus
    3. Take the bus from Big Pine Key - CVS / MM30 to N Roosevelt & 3rd Streetbus bus Lks
    2d 6h
    $394–1,788

  4. Drive 1,468.2 mi

    1. Drive from Chicago to Key Westcar car 1,468.2 mi
    27h 5m
    $268–387

  5. Fly from Chicago Midway International Airport

    1. Fly from Chicago Midway International Airport (MDW) to Key West International Airport (EYW)plane plane MDW - EYW
    6h 14m
    $164–768

  6. Train to South Bend, fly

    1. Take the train from Van Buren St. to South Bend Airporttrain train
    2. Fly from South Bend (SBN) to Key West International Airport (EYW)plane plane SBN - EYW
    8h 20m
    $204–927

  7. Train to General Mitchell International Airport, fly

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Key West International Airport (EYW)plane plane MKE - EYW
    8h 39m
    $245–1,131

Chicago to Key West by bus and foot

Calendar14Weekly Services
Duration39h 36mAverage Duration
Ticket$154Cheapest Price
See schedules

Questions & Answers

What companies run services between Chicago, IL, USA and Key West, FL, USA?

American Airlines, United Airlines, and two other airlines fly from Chicago O'Hare International Airport (ORD) to Key West International Airport (EYW) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to N Roosevelt & 3rd Street via Atlanta Bus Station, Miami Airport Station, Big Pine Key, and Big Pine Key - CVS / MM30 in around 39h 36m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers

Trips from Chicago

Trips to Key West

Popular routes