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

Find Transport to Estero

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There are 8 ways to get from Chicago to Estero by plane, bus (Greyhound, Flixbus), 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 Chicago Midway International Airport to Ft. Myers

    best
    1. Fly from Chicago Midway International Airport (MDW) to Ft. Myers (RSW)plane plane MDW - RSW
    6h 51m
    $156–760

  2. Fly Chicago O'Hare International Airport to Sarasota–Bradenton International Airport, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Sarasota–Bradenton International Airport (SRQ)plane plane ORD - SRQ
    2. Take the bus from Sarasota Cattlemen Transfer Center to Fort Myers Bus Stopbus bus
    10h 8m
    $92–422

  3. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to Tampa Bus Stationbus bus
    3. Take the bus from Tampa Bus Station to Fort Myers Bus Stopbus bus
    32h 50m
    $217–362

  4. Train, bus (Amtrak)

    1. Take the train from Chicago Union Station to Tampatrain train Floridian
    2. Take the bus from Tampa to Fort Myers Amtrak Bus Stopbus bus Amtrak Thruway Connecting Service
    45h 42m

  5. Drive  1,235.1 mi

    1. Drive from Chicago to Esterocar car 1,235.1 mi
    22h 26m
    $226–326

  6. Fly Chicago O'Hare International Airport to Ft. Myers

    1. Fly from Chicago O'Hare International Airport (ORD) to Ft. Myers (RSW)plane plane ORD - RSW
    7h 15m
    $126–410

  7. Train to General Mitchell International Airport, fly to Ft. Myers

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Ft. Myers (RSW)plane plane MKE - RSW
    8h 30m
    $212–891

  8. Fly Chicago Midway International Airport to Sarasota–Bradenton International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)plane plane MDW - SRQ
    2. Take the bus from Sarasota Cattlemen Transfer Center to Fort Myers Bus Stopbus bus
    9h 37m
    $128–632

Chicago to Estero by bus

Calendar5Weekly Buses
Duration32h 50mAverage Duration
Ticket$217Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Estero.ExpandLaunch map view
  • Distance: 1,139 mi
  • Duration: 6h 51m

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

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Ft. Myers (RSW) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to S Tamiami Trl @ Lychee Ln via Atlanta Bus Station, Tampa Bus Station, Rosa Parks Transportation Ctr, and South Fort Myers Transfer/P&R in around 32h 50m.

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