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

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There are 7 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
    $136–660

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Ft. Myers (RSW)plane plane ORD - RSW
    7h 15m
    $106–560

  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
    31h 40m
    $193–353

  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
    $641–1,276

  5. Drive 1,237.9 mi

    1. Drive from Chicago to Esterocar car 1,237.9 mi
    22h 33m
    $226–327

  6. 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 53m
    $176–832

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

    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 27m
    $146–682

Chicago to Estero by bus

Calendar7Weekly Buses
Duration31h 40mAverage Duration
Ticket$193Cheapest Price
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Questions & Answers

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 31h 40m.

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