Rome2Rio

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

Find Transport to Chicago

See all options

There are 8 ways to get from Saint Augustine to Chicago by bus, plane, bus (Flixbus, Greyhound), taxi, 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. Bus to Jacksonville, fly to Chicago Midway International Airport

    best
    1. Take the bus from St. Johns Adminsistration to Pearl St. & Bay St.bus bus
    2. Fly from Jacksonville (JAX) to Chicago Midway International Airport (MDW)plane plane JAX - MDW
    6h 45m
    $110–485

  2. Bus

    1. Take the bus from St. Johns Adminsistration to JRTC - Express Selectbus bus
    2. Take the bus from Jacksonville to Atlanta Bus Stationbus bus
    3. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    26h 1m
    $182–357

  3. Taxi, train (Amtrak)

    1. Take the taxi from Saint Augustine to Jacksonvilletaxi taxi
    2. Take the train from Jacksonville to Chicago Union Stationtrain train Floridian
    36h 7m
    $617–1,238

  4. Drive 1,016.2 mi

    1. Drive from Saint Augustine to Chicagocar car 1,016.2 mi
    19h 20m
    $186–268

  5. Bus to Jacksonville, fly to Chicago O'Hare International Airport

    1. Take the bus from St. Johns Adminsistration to Pearl St. & Bay St.bus bus
    2. Fly from Jacksonville (JAX) to Chicago O'Hare International Airport (ORD)plane plane JAX - ORD
    7h 17m
    $195–525

  6. Bus to Orlando, fly to Chicago Midway International Airport

    1. Take the bus from Jacksonville to Orlando Bus Stationbus bus
    2. Fly from Orlando (MCO) to Chicago Midway International Airport (MDW)plane plane MCO - MDW
    9h 16m
    $277–595

  7. Drive to Orlando Sanford, fly to South Bend, train

    1. Drive from Saint Augustine to Orlando-Sanford-Airport-SFBcar car
    2. Fly from Orlando Sanford (SFB) to South Bend (SBN)plane plane SFB - SBN
    3. Take the train from South Bend Airport to Van Buren St.train train
    7h 17m
    $169–738

  8. Bus to Orlando, fly to Chicago O'Hare International Airport

    1. Take the bus from Jacksonville to Orlando Bus Stationbus bus
    2. Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane plane MCO - ORD
    9h 39m
    $147–705

Jacksonville (JAX) to Chicago Midway International Airport (MDW) flights

Calendar50Weekly Planes
Duration3h 55mAverage Duration
Ticket$95Cheapest Price
See schedules

Questions & Answers

Map of how to get from Saint Augustine to Chicago.ExpandLaunch map view
  • Distance: 920.6 mi
  • Duration: 6h 45m

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

You can take a vehicle from Saint Augustine to Chicago Bus Station via St. Johns Adminsistration, JRTC - Express Select, Jacksonville, and Atlanta Bus Station in around 26h 1m.

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