Rome2Rio

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

Find Transport to Estero

See all options

There are 9 ways to get from Chicago to Estero by plane, bus (Flixbus, Greyhound), 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 52m
    $136–710

  2. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to Orlando Bus Stationbus bus
    3. Take the bus from Orlando Bus Station to Fort Myers Bus Stopbus bus
    31h 10m
    $155–326

  3. Train, bus

    1. Take the train from Chicago Union Station to Tampatrain train Floridian
    2. Take the bus from Tampa International Airport to Fort Myers 7-11bus bus Tampa
    44h 31m
    $249–621

  4. Drive 1,236.7 mi

    1. Drive from Chicago to Esterocar car 1,236.7 mi
    22h 26m
    $226–326

  5. 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 22m
    $176–400

  6. Fly Chicago Midway International Airport to Tampa, bus

    1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane plane MDW - TPA
    2. Take the bus from Tampa International Airport to Fort Myers 7-11bus bus
    7h 43m
    $160–745

  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 34m
    $207–1,021

  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 50m
    $176–850

  9. 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 31m
    $146–800

Chicago to Estero by bus

Calendar27Weekly Buses
Duration31h 10mAverage Duration
Ticket$155Cheapest Price
See schedules

Questions & Answers

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, Orlando Bus Station, Rosa Parks Transportation Ctr, and South Fort Myers Transfer/P&R in around 31h 10m.

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 Estero

Popular routes