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How to get fromEstero to Chicagoby plane, bus (Greyhound, Flixbus), bus, train, or car

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There are 6 ways to get from Estero to Chicago by plane, bus (Greyhound, Flixbus), bus, train, 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 Ft. Myers to Chicago Midway International Airport

    best
    1. Fly from Ft. Myers (RSW) to Chicago Midway International Airport (MDW)plane plane RSW - MDW
    6h 21m
    $106–510

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

    cheapest
    1. Fly from Ft. Myers (RSW) to Chicago O'Hare International Airport (ORD)plane plane RSW - ORD
    6h 50m
    $96–450

  3. Bus

    1. Take the bus from Fort Myers 7-11 to Tallahassee, FLbus bus
    2. Take the bus from Tallahassee to Nashville Bus Stationbus bus
    3. Take the bus from Nashville Bus Station to Chicago Bus Stationbus bus
    32h 13m
    $256–503

  4. Bus, train (Amtrak)

    1. Take the bus from Fort Myers Amtrak Bus Stop to Tampabus bus Amtrak Thruway Connecting Service
    2. Take the train from Tampa to Chicago Union Stationtrain train Floridian
    45h 42m
    $575–1,225

  5. Drive  1,236.4 mi

    1. Drive from Estero to Chicagocar car 1,236.4 mi
    22h 26m
    $226–326

  6. Bus to Sarasota–Bradenton International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Fort Myers Bus Stop to Sarasota Cattlemen Transfer Centerbus bus
    2. Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW)plane plane SRQ - MDW
    9h 22m
    $146–681

Ft. Myers (RSW) to Chicago Midway International Airport (MDW) flights

Calendar39Weekly Planes
Duration3h 59mAverage Duration
Ticket$106Cheapest Price
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Questions & Answers

Map of how to get from Estero to Chicago.ExpandLaunch map view
  • Distance: 1,139.3 mi
  • Duration: 6h 21m

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

Southwest Airlines and Delta fly from Ft. Myers (RSW) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a bus from S Tamiami Trl @ County Rd to Chicago Bus Station via South Fort Myers Transfer/P&R, Fort Myers 7-11, Tallahassee, FL, Tallahassee, and Nashville Bus Station in around 32h 13m.

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