Rome2Rio

How to get fromChicago to Cheshireby plane, train, bus (Flixbus, Greyhound), train (Amtrak), car, bus, or bus (Greyhound)

Find Transport to Cheshire

See all options

There are 12 ways to get from Chicago to Cheshire by plane, train, bus (Flixbus, Greyhound), train (Amtrak), car, bus, or bus (Greyhound)

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 Chicago Midway International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to New Haventrain train
    7h 55m
    $224–595

  2. Fly Chicago O'Hare International Airport to Bradley International Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    7h 49m
    $94–447

  3. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from Port Authority Bus Terminal to New Haven Bus Stopbus bus Greyhound US0240 / ...
    21h 30m
    $154–282

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Springfieldtrain train Lake Shore Limited
    2. Take the train from Springfield to New Haventrain train Amtrak Hartford Line / ...
    22h 49m
    $312–652

  5. Drive 870.7 mi

    1. Drive from Chicago to Cheshirecar car 870.7 mi
    14h 32m
    $159–230

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to New Haventrain train
    8h 15m
    $234–695

  7. Fly Chicago Midway International Airport to Bradley International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    7h 18m
    $118–547

  8. Fly Chicago O'Hare International Airport to Tweed-New Haven Airport, line 206 bus, line 229 bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane plane ORD - HVN
    2. Take the bus from Lighthouse Park Terminus to Chapel St @ Orange Stbus bus
    3. Take the bus from Church St @ Chapel St to S Main St @ Wallingford Rdbus bus
    7h 33m
    $176–495

  9. Fly Chicago O'Hare International Airport to Westchester County Airport, line 971 bus, train, line 229 bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from Main St @ South Broadway to Stamford Transportation Center @ Bay Abus bus
    3. Take the train from Stamford to New Haventrain train
    4. Take the bus from Church St @ Chapel St to S Main St @ Wallingford Rdbus bus
    9h 27m
    $112–1,116

  10. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from Providence to New Haventrain train
    9h 2m
    $106–1,036

  11. Train via New York (Amtrak)

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to New Haventrain train Northeast Regional / ...
    23h 55m
    $323–1,233

  12. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the bus from Port Authority Bus Terminal to New Haven Bus Stopbus bus
    25h 41m
    $172–395

Chicago to Cheshire by bus and foot

Calendar32Weekly Services
Duration21h 30mAverage Duration
Ticket$154Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chicago to Cheshire.ExpandLaunch map view
  • Distance: 828 mi
  • Duration: 7h 55m

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

You can take a bus from Chicago Bus Station to S Main St @ Wallingford Rd via New York Midtown, Port Authority Bus Terminal, New Haven Bus Stop, and Church St @ Chapel St in around 21h 30m. Alternatively, you can take a train from Chicago Union Station to S Main St @ Wallingford Rd via Springfield, New Haven, and Church St @ Chapel St in around 22h 49m.

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