Rome2Rio

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

Find Transport to Chicago

See all options

There are 8 ways to get from Bend to Chicago by plane, bus, train, bus (Flixbus, 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. Fly Roberts Field-Redmond Municipal Airport to Chicago O'Hare International Airport

    best
    1. Fly from Roberts Field-Redmond Municipal Airport (RDM) to Chicago O'Hare International Airport (ORD)plane plane RDM - ORD
    8h 27m
    $174–763

  2. Bus to Portland International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Hawthorne Station, Bend to Portland International Airportbus bus
    2. Fly from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD)plane plane PDX - ORD
    9h 34m
    $159–716

  3. Bus, train

    1. Take the bus from Bend Hawthorne Station to Portland Union Stationbus bus Bend to Portland Express
    2. Take the train from Portland to Chicago Union Stationtrain train Empire Builder
    2d 3h
    $621–1,466

  4. Bus

    1. Take the bus from Bend Hawthorne Station to Portland Union Stationbus bus
    2. Take the bus from Portland Curbside Bus Stop to Pasco Bus Stopbus bus
    3. Take the bus from Pasco Bus Stop to Denver Union Stationbus bus
    4. Take the bus from Denver Union Station to Chicago Bus Stationbus bus
    2d 6h
    $388–796

  5. Drive 1,989.6 mi

    1. Drive from Bend to Chicagocar car 1,989.6 mi
    33h 3m
    $364–525

  6. Amtrak Thruway to Mahlon Sweet Field Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Bend, OR to Jaqua Academic Center - Eugenebus bus
    2. Fly from Mahlon Sweet Field Airport (EUG) to Chicago O'Hare International Airport (ORD)plane plane EUG - ORD
    8h 54m
    $180–644

  7. Bus to Portland International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Hawthorne Station, Bend to Portland International Airportbus bus
    2. Fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW)plane plane PDX - MDW
    9h 21m
    $199–866

  8. Fly Roberts Field-Redmond Municipal Airport to General Mitchell International Airport, train

    1. Fly from Roberts Field-Redmond Municipal Airport (RDM) to General Mitchell International Airport (MKE)plane plane RDM - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    10h 48m
    $387–1,672

Bend to Chicago by bus and train

Calendar11Weekly Services
Duration2d 3hAverage Duration
Ticket$621Cheapest Price
See schedules

Questions & Answers

What companies run services between Bend, OR, USA and Chicago, IL, USA?

United Airlines, Alaska Airlines, Inc., and two other airlines fly from Roberts Field-Redmond Municipal Airport (RDM) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, you can take a bus from Bend Hawthorne Station to Chicago Bus Station via Portland Union Station, Portland Curbside Bus Stop, Pasco Bus Stop, and Denver Union Station in around 2d 6h.

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

More Questions & Answers

Where to next?

Trips from Bend

Trips to Chicago

Popular routes