Rome2Rio

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

Find Transport to Chicago

See all options

There are 11 ways to get from Darien to Chicago by train, plane, train (Amtrak), bus, car, or bus (Flixbus)

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 O'Hare International Airport

    best
    1. Take the train from Darien to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)planeLGA - ORD
    5h 47m
    $65–289

  2. Train

    1. Take the train from Darien to 125th Street - Harlemtrain
    2. Take the train from 125th Street - Harlem to Croton-Harmontrain
    3. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain
    21h 51m
    $151–404

  3. Train, bus

    1. Take the train from Darien to Grand Central Terminaltrain
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus
    24h 46m
    $119–340

  4. Drive 822.5 mi

    1. Drive from Darien to Chicagocar822.5 mi
    13h 39m
    $151–217

  5. Train to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Darien to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    5h 36m
    $90–459

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

    1. Take the train from Darien to Grand Central Terminaltrain
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)planeJFK - ORD
    6h 22m
    $827–1,041

  7. Line 971 bus to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Stamford Transportation Center @ Bay A to South Broadway @ Main Stbus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)planeHPN - ORD
    7h 12m
    $78–382

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

    1. Take the train from Stamford Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)planeEWR - ORD
    7h 30m
    $70–1,045

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

    1. Take the train from Darien to New Haventrain
    2. Take the train from New Haven to Windsor Lockstrain
    3. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)planeBDL - MDW
    7h 55m
    $111–715

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

    1. Take the train from Darien to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)planeLGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain
    8h 9m
    $207–624

  11. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    24h 56m
    $102–240

Darien to Chicago by train

Calendar7Weekly Trains
Duration21h 51mAverage Duration
Ticket$151Cheapest Price
See schedules

Questions & Answers

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

You can take a train from Darien to Chicago Union Station via 125th Street - Harlem and Croton-Harmon Amtrak Station in around 21h 51m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station once daily. Tickets cost $90–220 and the journey takes 20h 25m.

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 Darien

Trips to Chicago

Popular routes