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

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

    best
    1. Take the subway from Quincy 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 35m
    $226–697

  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
    3. Take the train from New Haven to South Norwalktrain train
    10h 43m
    $140–564

  3. Train

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    2. Take the train from White Plains to Brewstertrain train Harlem
    23h 57m
    $525–805

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from Port Authority Bus Terminal to Stamford Bus Stopbus bus
    3. Take the bus from Norwalk Wheels Hub to Pulse Pointbus bus 15
    26h 47m

  5. Drive  836.9 mi

    1. Drive from Chicago Union Station to Enterprise Rent a Carcar car 836.9 mi
    13h 55m
    $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 48m
    $156–537

  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 42m

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

    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 Airport Railroad Station to New York Penn Stationtrain train
    3. Take the train from Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Stationtrain train
    4. Take the train from South Norwalk to Danburytrain train
    9h 22m
    $168–1,460

  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
    10h 19m
    $180–784

  10. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to New Yorkbus bus
    3. Take the train from Grand Central Terminal to Danburytrain train
    27h 21m
    $204–322

Chicago Union Station to Enterprise Rent a Car by train, bus, and foot

Calendar7Weekly Services
Duration23h 57mAverage Duration
Ticket$525Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago Union Station to Enterprise Rent a Car.ExpandLaunch map view
  • Distance: 805.6 mi
  • Duration: 8h 35m

What companies run services between Chicago Union Station, 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 Amtrak Station, Croton Harmon Railroad Station, White Plains Bus Terminal Lane B, White Plains, Brewster, Brewster Village Mta, and Federal Road Park & Ride in around 23h 57m. Alternatively, you can take a vehicle from Chicago Union Station to Enterprise Rent a Car via Chicago Bus Station, New York Midtown, Port Authority Bus Terminal, Stamford Bus Stop, Stamford Transportation Center @ Bay E, Belden Ave @ opp Burnell Blvd, Norwalk Wheels Hub, and Pulse Point in around 26h 47m.

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