Rome2Rio

How to get fromChicago Station (CTA Logan Square branch) to Florida Keysby plane, bus (Greyhound), train, bus, car or shuttle

Find Transport to Florida Keys

See all options

There are 8 ways to get from Chicago Station (CTA Logan Square branch) to Florida Keys by plane, bus (Greyhound), train, bus, car, or shuttle

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 Chicago O'Hare International Airport to Key West International Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Key West International Airport (EYW)planeORD - EYW
    8h 5m
    $162–459

  2. Bus (Greyhound)

    1. Take the bus from Chicago Train Station to Atlanta Bus Stationbus
    2. Take the bus from Atlanta Bus Station to Miami Airport Stationbus
    3. Take the bus from Miami Airport Station to Big Pine Keybus
    38h 30m
    $167–469

  3. Train, bus

    1. Take the train from Chicago Union Station to Miami Amtrak StationtrainFloridian
    2. Take the bus from Miami Airport Station to Big Pine KeybusGreyhound US0720s
    2d 6h
    $301–828

  4. Drive 1,455.7 mi

    1. Drive from Chicago Station (CTA Logan Square branch) to Florida Keyscar1,455.7 mi
    26h 29m
    $266–384

  5. Fly Chicago Midway International Airport to Key West International Airport

    1. Fly from Chicago Midway International Airport (MDW) to Key West International Airport (EYW)planeMDW - EYW
    9h 48m
    $171–676

  6. Fly Chicago O'Hare International Airport to Miami International Airport, shuttle

    1. Fly from Chicago O'Hare International Airport (ORD) to Miami International Airport (MIA)planeORD - MIA
    2. Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FLshuttle
    10h 33m
    $186–494

  7. Fly Chicago Midway International Airport to Fort Lauderdale–Hollywood International Airport, shuttle

    1. Fly from Chicago Midway International Airport (MDW) to Fort Lauderdale–Hollywood International Airport (FLL)planeMDW - FLL
    2. Take a shuttle bus from Fort Lauderdale, FL - International Airport to Big Pine Key, FLshuttle
    10h 52m
    $231–561

  8. Fly Chicago Midway International Airport to Miami International Airport, shuttle

    1. Fly from Chicago Midway International Airport (MDW) to Miami International Airport (MIA)planeMDW - MIA
    2. Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FLshuttle
    10h 32m
    $216–581

Chicago Station (CTA Logan Square branch) to Florida Keys by bus and foot (Greyhound)

Calendar9Weekly Services
Duration38h 30mAverage Duration
Ticket$167Cheapest Price
See schedules

Questions & Answers

What companies run services between Chicago Station (CTA Logan Square branch), IL, USA and Florida Keys, 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 & Paulina to Florida Keys via Chicago & Michigan, Michigan & Superior, Union Station Transit Center, Chicago Train Station, Atlanta Bus Station, Miami Airport Station, Big Pine Key, Big Pine Key - CVS / MM30, and Sugarloaf Key - Lower - Sugarloaf Lodge in around 38h 30m.

Transport is disrupted due to the Russia-Ukraine war. Read more

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 Station (CTA Logan Square branch)

Trips to Florida Keys

Popular routes