Rome2Rio

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

Find Transport to Chicago

See all options

There are 8 ways to get from Estero to Chicago by plane, bus (Greyhound, Flixbus), bus, train, car, or taxi

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
    $116–560

  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 54m
    $100–460

  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 8m
    $282–528

  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
    $653–1,338

  5. Drive 1,237.9 mi

    1. Drive from Estero to Chicagocar car 1,237.9 mi
    22h 26m
    $226–327

  6. Taxi to Punta Gorda Airport, fly to Chicago Midway International Airport

    1. Take the taxi from South Fort Myers Transfer/P&R to Punta Gorda Airport (PGD)taxi taxi
    2. Fly from Punta Gorda Airport (PGD) to Chicago Midway International Airport (MDW)plane plane PGD - MDW
    5h 39m
    $188–558

  7. Taxi to Punta Gorda Airport, fly to South Bend, train

    1. Take the taxi from South Fort Myers Transfer/P&R to Punta Gorda Airport (PGD)taxi taxi
    2. Fly from Punta Gorda Airport (PGD) to South Bend (SBN)plane plane PGD - SBN
    3. Take the train from South Bend Airport to Van Buren St.train train
    7h 49m
    $254–828

  8. 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 24m
    $136–633

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

Calendar43Weekly Planes
Duration4h 11mAverage Duration
Ticket$112Cheapest Price
See schedules

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 8m.

Airlines
Train operators
Bus operators
Other 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