Rome2Rio

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

Find Transport to Chicago

See all options

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

    best
    1. Take the train from New Haven to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 30m
    $103–546

  2. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from New Haven to Stamfordtrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 53m
    $68–990

  3. Train (Amtrak)

    1. Take the train from New Haven to Springfieldtrain train Amtrak Hartford Line / ...
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    23h 29m
    $140–808

  4. Bus

    1. Take the bus from New Haven Union Station to Port Authority Bus Terminalbus bus Providence
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    25h 17m
    $103–267

  5. Drive 871.1 mi

    1. Drive from Guilford to Chicagocar car 871.1 mi
    14h 47m
    $159–230

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

    1. Take the train from New Haven to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    7h 45m
    $73–336

  7. Train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from New Haven to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    6h 56m
    $101–756

  8. Train to Bradley International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from New Haven to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    7h 17m
    $71–606

  9. Train, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the train from Guilford to New Londontrain train
    2. Take the train from New London to Providencetrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    8h 2m
    $81–649

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

    1. Take the train from New Haven 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
    10h 1m
    $235–751

  11. Train via New York (Amtrak)

    1. Take the train from New Haven 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 / ...
    23h 35m
    $133–1,087

Guilford to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration23h 29mAverage Duration
Ticket$140Cheapest Price
See schedules

Questions & Answers

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

You can take a train from Guilford to Chicago Union Station via New Haven and Springfield in around 23h 29m. Alternatively, you can take a bus from State St @ Boston Post Rd to Chicago Bus Station via Church St @ George St, George St @ opp Orange St, Union Ave @ Union Station, New Haven Union Station, Port Authority Bus Terminal, and New York Midtown in around 25h 17m.

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 Guilford

Trips to Chicago

Popular routes