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How to get fromChicago to Enterprise Rent a Carby subway, plane, train, train (Amtrak), bus or car

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There are 10 ways to get from Chicago to Enterprise Rent a Car by subway, plane, train, train (Amtrak), bus, 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. Subway to Chicago Midway International Airport, fly to Laguardia Airport, train

    best
    1. Take the subway from Roosevelt to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    3. Take the train from 125th Street - Harlem to South Norwalktrain train
    4. Take the train from South Norwalk to Danburytrain train
    8h 6m
    $110–526

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Newark Liberty International Airport to Stamford Amtrak Stationtrain train
    9h 45m
    $74–512

  3. Train

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train
    2. Take the train from Croton-Harmon to 125th Street - Harlemtrain train
    3. Take the train from 125th Street - Harlem to Danburytrain train
    24h 16m
    $278–584

  4. Bus, train

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Stationtrain train
    3. Take the bus from Norwalk Wheels Hub to Pulse Pointbus bus 15
    25h 20m

  5. Drive 836 mi

    1. Drive from Chicago to Enterprise Rent a Carcar car 836 mi
    13h 54m
    $153–221

  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 South Norwalktrain train
    3. Take the train from South Norwalk to Danburytrain train
    8h 27m
    $76–326

  7. Fly Chicago O'Hare International Airport to Westchester County Airport, train, line 12 bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from White Plains to Brewstertrain train
    3. Take the bus from Brewster Village Mta to Federal Road Park & Ridebus bus
    8h 18m

  8. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Jamaica to Grand Central Terminaltrain train
    3. Take the train from Grand Central Terminal to South Norwalktrain train
    4. Take the train from South Norwalk to Danburytrain train
    8h 48m
    $82–318

  9. 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
    3. Take the train from New Haven to South Norwalktrain train
    9h 54m
    $130–850

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

    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
    3. Take the train from New Haven to South Norwalktrain train
    10h 25m
    $100–640

Chicago to Enterprise Rent a Car by train and bus

Calendar7Weekly Services
Duration24h 16mAverage Duration
Ticket$278Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Enterprise Rent a Car, CT, USA?

You can take a train from Chicago Union Station to Enterprise Rent a Car via Croton-Harmon, 125th Street - Harlem, Danbury, and White Street and Patriot Drive in around 24h 16m.

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