Rome2Rio

How to get fromIssaquah to Chicagoby plane, train (Amtrak), car, train or bus

Find Transport to Chicago

See all options

There are 6 ways to get from Issaquah to Chicago by plane, train (Amtrak), car, train, or bus

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 Chicago O'Hare International Airport

    best
    1. Fly from Seattle-Tacoma International Airport (SEA) to Chicago O'Hare International Airport (ORD)planeSEA - ORD
    7h 2m
    $103–441

  2. Train (Amtrak)

    1. Take the train from Seattle to Chicago Union StationtrainEmpire Builder
    47h 28m
    $283–753

  3. Drive 1,999.2 mi

    1. Drive from Issaquah to Chicagocar1,999.2 mi
    31h 42m
    $365–527

  4. Fly to Chicago Midway International Airport

    1. Fly from Seattle-Tacoma International Airport (SEA) to Chicago Midway International Airport (MDW)planeSEA - MDW
    6h 51m
    $138–661

  5. Fly to General Mitchell International Airport, train

    1. Fly from Seattle-Tacoma International Airport (SEA) to General Mitchell International Airport (MKE)planeSEA - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain
    9h 7m
    $251–1,126

  6. Bus, train

    1. Take the bus from Seattle Amtrak Station to Columbia Stationbus
    2. Take the train from Wenatchee Amtrak to St. Paul-Minneapolistrain
    3. Take the bus from Saint Paul Union Depot to Chicago Bus Stationbus
    2d
    $228–628

Issaquah to Chicago by bus and train (Amtrak)

Calendar11Weekly Services
Duration47h 28mAverage Duration
Ticket$283Cheapest Price
See schedules

Questions & Answers

What companies run services between Issaquah, WA, USA and Chicago, IL, USA?

American Airlines, Alaska Airlines, Inc., and three other airlines fly from Seattle-Tacoma International Airport (SEA) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, Amtrak operates a train from Seattle to Chicago Union Station twice daily. Tickets cost $280–750 and the journey takes 45h 50m.

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

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

Where to next?

Trips from Issaquah

Trips to Chicago

Popular routes