Rome2Rio

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

Find Transport to Chicago

See all options

There are 11 ways to get from Stamford to Chicago by train, plane, train (Amtrak), bus (Greyhound, Flixbus), car, 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. Train to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 47m
    $95–488

  2. Train to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Stamford Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 47m
    $58–1,036

  3. Train (Amtrak)

    1. Take the train from Stamford Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train Northeast Regional
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 21m
    $115–891

  4. Bus

    1. Take the bus from Stamford Bus Stop to Port Authority Bus Terminalbus bus Greyhound US0240
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    23h 21m
    $99–164

  5. Drive 818.5 mi

    1. Drive from Stamford to Chicagocar car 818.5 mi
    13h 43m
    $150–216

  6. Train to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 5m
    $65–278

  7. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Stamford to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 30m
    $776–1,040

  8. Fly Westchester County Airport to Chicago O'Hare International Airport

    1. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    6h 27m
    $62–322

  9. Train, train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from Stamford to New Haventrain train
    2. Take the train from New Haven to Windsor Lockstrain train
    3. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    8h 8m
    $99–1,241

  10. Train to Laguardia Airport, fly to General Mitchell International Airport, train

    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 17m
    $227–633

  11. Train, bus

    1. Take the train from Stamford to Grand Central Terminaltrain train
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    24h 53m
    $118–229

Stamford to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration21h 21mAverage Duration
Ticket$115Cheapest Price
See schedules

Questions & Answers

What companies run services between Stamford, CT, USA and Chicago, IL, USA?

You can take a train from Stamford Amtrak Station to Chicago Union Station via Ny Moynihan Train Hall At Penn Station in around 21h 21m. Alternatively, you can take a bus from Stamford Bus Stop to Chicago Bus Station via Port Authority Bus Terminal and New York Midtown in around 23h 21m.

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 Stamford

Trips to Chicago

Popular routes