Rome2Rio

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

Find Transport to Chicago

See all options

There are 8 ways to get from Waterloo to Chicago by bus, plane, train, bus (Greyhound), 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 Rochester, fly to Chicago Midway International Airport

    best
    1. Take the bus from Geneva to Rochesterbus bus
    2. Fly from Rochester (ROC) to Chicago Midway International Airport (MDW)plane plane ROC - MDW
    4h 41m
    $146–593

  2. Drive  636.1 mi

    cheapest
    1. Drive from Waterloo to Chicagocar car 636.1 mi
    10h 52m
    $117–168

  3. Bus, train

    1. Take the bus from Geneva to Rochesterbus bus Adt N806-D / ...
    2. Take the train from Rochester to Chicago Union Stationtrain train Lake Shore Limited
    13h 42m
    $360–565

  4. Bus

    1. Take the bus from Geneva to Buffalobus bus
    2. Take the bus from Buffalo to Cleveland Bus Stationbus bus
    3. Take the bus from Cleveland Bus Station to Chicago Bus Stationbus bus
    15h 29m
    $134–250

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

    1. Take the bus from Geneva to Rochesterbus bus
    2. Fly from Rochester (ROC) to Chicago O'Hare International Airport (ORD)plane plane ROC - ORD
    5h 4m
    $126–503

  6. Bus to Buffalo Niagara International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Geneva to Buffalobus bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    5h 56m
    $210–415

  7. Bus to Buffalo Niagara International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Geneva to Buffalobus bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    6h 21m
    $220–405

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

    1. Take the bus from Dill St & North St to C22bus bus
    2. Fly from Syracuse Hancock International Airport (SYR) to Chicago O'Hare International Airport (ORD)plane plane SYR - ORD
    7h 4m
    $186–566

Rochester (ROC) to Chicago Midway International Airport (MDW) flights

Calendar31Weekly Planes
Duration2h 55mAverage Duration
Ticket$87Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Waterloo to Chicago.ExpandLaunch map view
  • Distance: 589.3 mi
  • Duration: 4h 41m

What companies run services between Waterloo, NY, USA and Chicago, IL, USA?

You can take a vehicle from Waterloo to Chicago Bus Station via Geneva, Buffalo, and Cleveland Bus Station in around 15h 29m.

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

Booking & Getting There