Rome2Rio

How to get fromChicago to Islamoradaby plane, shuttle, bus (Greyhound, Flixbus), train, bus, car or bus (Greyhound)

Find Transport to Islamorada

See all options

There are 10 ways to get from Chicago to Islamorada by plane, shuttle, bus (Greyhound, Flixbus), train, bus, car, or bus (Greyhound)

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 Miami International Airport, shuttle

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Miami International Airport (MIA)plane plane ORD - MIA
    2. Take a shuttle bus from Miami, FL - International Airport to Islamorada, FLshuttle bus
    7h 41m
    $172–465

  2. Fly Chicago O'Hare International Airport to Key West International Airport, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Key West International Airport (EYW)plane plane ORD - EYW
    2. Take the bus from Key West Airport to Islamoradabus bus
    8h 12m
    $146–510

  3. 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 Islamoradabus bus
    33h 30m
    $190–466

  4. Train, bus

    1. Take the train from Chicago Union Station to Hollywood Amtrak Stationtrain train Floridian
    2. Take the bus from Miami Airport Station to Islamoradabus bus Greyhound US0720s
    2d 2h
    $569–1,232

  5. Drive 1,387.6 mi

    1. Drive from Chicago to Islamoradacar car 1,387.6 mi
    25h 15m
    $254–366

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

    1. Fly from Chicago Midway International Airport (MDW) to Miami International Airport (MIA)plane plane MDW - MIA
    2. Take a shuttle bus from Miami, FL - International Airport to Islamorada, FLshuttle bus
    7h 11m
    $232–695

  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)plane plane MDW - FLL
    2. Take a shuttle bus from Fort Lauderdale, FL - International Airport to Islamorada, FLshuttle bus
    7h 41m
    $228–615

  8. Fly Chicago O'Hare International Airport to Fort Lauderdale–Hollywood International Airport, shuttle

    1. Fly from Chicago O'Hare International Airport (ORD) to Fort Lauderdale–Hollywood International Airport (FLL)plane plane ORD - FLL
    2. Take a shuttle bus from Fort Lauderdale, FL - International Airport to Islamorada, FLshuttle bus
    8h 5m
    $172–465

  9. Fly Chicago O'Hare International Airport to Palm Beach International Airport, train, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Palm Beach International Airport (PBI)plane plane ORD - PBI
    2. Take the train from West Palm Beach Station to Miami Airport Stationtrain train
    3. Take the bus from Miami Airport Station to Islamoradabus bus
    11h 18m
    $272–692

  10. Bus via Pembroke Pines (Greyhound)

    1. Take the bus from Chicago Train Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to Hollywood Sheridan Trirail Stationbus bus
    3. Take the bus from Miami Airport Station to Islamoradabus bus
    37h 56m
    $233–462

Chicago to Islamorada by bus

Calendar14Weekly Buses
Duration33h 30mAverage Duration
Ticket$190Cheapest Price
See schedules

Questions & Answers

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

You can take a bus from Chicago Bus Station to Islamorada via Atlanta Bus Station and Miami Airport Station in around 33h 30m.

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 Islamorada

Popular routes