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

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There are 6 ways to get from Chesapeake to Milwaukee by plane, train (Amtrak), 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 to General Mitchell International Airport

    best
    1. Fly from Norfolk International Airport (ORF) to General Mitchell International Airport (MKE)plane plane ORF - MKE
    4h 46m
    $151–686

  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 13m
    $102–391

  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
    $346–710

  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 38m
    $223–403

  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 40m
    $131–476

Chesapeake to Milwaukee by train (Amtrak)

Calendar7Weekly Trains
Duration26h 34mAverage Duration
Ticket$346Cheapest Price
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Questions & Answers

Map of how to get from Chesapeake to Milwaukee.ExpandLaunch map view
  • Distance: 761.4 mi
  • Duration: 4h 46m

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

Southwest Airlines, Delta, 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.

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