Rome2Rio

How to get fromChicago to Lake Oswegoby plane, train (Amtrak), car or train

Find Transport to Lake Oswego

See all options

There are 5 ways to get from Chicago to Lake Oswego by plane, train (Amtrak), car, or train

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 from Chicago Midway International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Portland International Airport (PDX)planeMDW - PDX
    7h 39m
    $196–858

  2. Fly from Chicago O'Hare International Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX)planeORD - PDX
    7h 58m
    $96–478

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to PortlandtrainEmpire Builder
    47h 9m
    $290–800

  4. Drive 2,084.5 mi

    1. Drive from Chicago to Lake Oswegocar2,084.5 mi
    33h 36m
    $381–550

  5. Train to South Bend, fly

    1. Take the train from Van Buren St. to South Bend Airporttrain
    2. Fly from South Bend (SBN) to Portland International Airport (PDX)planeSBN - PDX
    11h 44m
    $246–1,017

Chicago to Lake Oswego by train and bus (Amtrak)

Calendar11Weekly Services
Duration47h 9mAverage Duration
Ticket$290Cheapest Price
See schedules

Questions & Answers

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

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Portland International Airport (PDX) 5 times a day. Alternatively, Amtrak operates a train from Chicago Union Station to Portland twice daily. Tickets cost $290–800 and the journey takes 46h 12m.

Transport is disrupted due to the Russia-Ukraine war. Read more

Airlines
Train 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

Trips from Chicago

Trips to Lake Oswego

Popular routes