Rome2Rio

How to get fromChesapeake to Milwaukeeby plane, train (Amtrak), train, bus, car, or bus (Flixbus, Greyhound)

Find Transport to Milwaukee

See all options

There are 7 ways to get from Chesapeake to Milwaukee by plane, train (Amtrak), train, bus, car, or bus (Flixbus, Greyhound)

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 to General Mitchell International Airport

    best
    1. Fly from Norfolk International Airport (ORF) to General Mitchell International Airport (MKE)plane plane ORF - MKE
    4h 51m
    $141–686

  2. Fly to Chicago O'Hare International Airport, bus

    cheapest
    1. Fly from Norfolk International Airport (ORF) to Chicago O'Hare International Airport (ORD)plane plane ORF - ORD
    2. Take the bus from Chicago to Milwaukee Intermodal Stationbus bus
    5h 25m
    $104–379

  3. Train (Amtrak)

    1. Take the train from Norfolk to Petersburg Amtrak Stationtrain train
    2. Take the train from Petersburg Amtrak Station to Chicago Union Stationtrain train
    3. Take the train from Chicago Union Station to Milwaukeetrain train
    26h 34m
    $581–946

  4. Train, bus

    1. Take the train from Norfolk to Washington Union Stationtrain train
    2. Take the bus from Washington Union Station to Chicago Bus Stationbus bus
    3. Take the bus from Multi-Modal/Rental Car Facility to Milwaukee Intermodal/Amtrak Stationbus bus
    26h 34m
    $285–429

  5. Drive  931.8 mi

    1. Drive from Chesapeake to Milwaukeecar car 931.8 mi
    16h 51m
    $171–246

  6. Fly to Chicago Midway International Airport, train

    1. Fly from Norfolk International Airport (ORF) to Chicago Midway International Airport (MDW)plane plane ORF - MDW
    2. Take the train from Chicago Union Station to Milwaukeetrain train
    5h 45m
    $150–543

  7. Bus

    1. Take the bus from Norfolk to Philadelphia Bus Stationbus bus
    2. Take the bus from Philadelphia Bus Station to Chicago Bus Stationbus bus
    3. Take the bus from Chicago Bus Station to Milwaukee Intermodal Stationbus bus
    30h 49m
    $196–316

Chesapeake to Milwaukee by train (Amtrak)

Calendar7Weekly Trains
Duration26h 34mAverage Duration
Ticket$581Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Chesapeake to Milwaukee.ExpandLaunch map view
  • Distance: 761.4 mi
  • Duration: 4h 51m

What companies run services between Chesapeake, City of Chesapeake, VA, USA and Milwaukee, WI, USA?

Southwest Airlines, American Airlines, and two other airlines fly from Norfolk International Airport (ORF) to General Mitchell International Airport (MKE) hourly. Alternatively, you can take a train from Norfolk to Milwaukee via Petersburg Amtrak Station and Chicago Union Station in around 26h 34m.

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