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How to get fromOakland City to Chicagoby taxi, plane, bus, train, or car

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There are 6 ways to get from Oakland City to Chicago by taxi, plane, bus, 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. Taxi to Evansville, fly

    best
    1. Take the taxi from Oakland City to Evansville (EVV)taxi taxi
    2. Fly from Evansville (EVV) to Chicago O'Hare International Airport (ORD)plane plane EVV - ORD
    3h 17m
    $96–315

  2. Drive 263.9 mi

    cheapest
    1. Drive from Oakland City to Chicagocar car 263.9 mi
    5h 47m
    $49–70

  3. Taxi, bus

    1. Take the taxi from Oakland City to Dale, IN - Denny'staxi taxi
    2. Take the bus from Dale, IN - Denny's to Indianapolis Union Stationbus bus
    3. Take the bus from Indianapolis Union Station to Chicago Bus Stationbus bus
    8h 57m
    $139–197

  4. Taxi, bus, train

    1. Take the taxi from Oakland City to Daletaxi taxi
    2. Take the bus from Dale to Indianapolisbus bus
    3. Take the train from Indianapolis to Chicago Union Stationtrain train
    10h 17m

  5. Taxi to Owensboro–Daviess County Regional Airport, fly

    1. Take the taxi from Oakland City to Owensboro–Daviess County Regional Airport (OWB)taxi taxi
    2. Fly from Owensboro–Daviess County Regional Airport (OWB) to Chicago O'Hare International Airport (ORD)plane plane OWB - ORD
    4h 5m
    $203–358

  6. Taxi, bus via Bloomington

    1. Take the taxi from Oakland City to Dale, IN - Denny'staxi taxi
    2. Take the bus from Dale, IN - Denny's to Bloomington, INbus bus
    3. Take the bus from Bloomington to Chicago Bus Stationbus bus
    9h 7m
    $130–187

Evansville (EVV) to Chicago O'Hare International Airport (ORD) flights

Calendar14Weekly Planes
Duration2h 3mAverage Duration
Ticket$37Cheapest Price
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Questions & Answers

Map of how to get from Oakland City to Chicago.ExpandLaunch map view
  • Distance: 315.7 mi
  • Duration: 3h 17m

What companies run services between Oakland City, IN, USA and Chicago, IL, USA?

There is no direct connection from Oakland City to Chicago. However, you can take the taxi to Evansville (EVV) airport, fly to Chicago O'Hare International Airport (ORD), walk to O'Hare, then take the subway to Jackson-Blue. Alternatively, you can take the taxi to Dale, IN - Denny's, take the bus to Indianapolis Union Station, then take the bus to Chicago Bus Station.

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