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How to get fromChicago Union Station to Enterprise Rent a Carby subway, plane, train, bus (Flixbus, Greyhound), train (Amtrak), 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, bus (Flixbus, Greyhound), train (Amtrak), 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 30m
    $206–597

  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 48m
    $112–465

  3. 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
    23h 42m

  4. 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 15m
    $327–646

  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 49m
    $236–697

  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 39m

  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
    9h 2m
    $348–908

  9. 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 32m
    $206–1,459

  10. 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
    $138–575

Chicago Midway International Airport (MDW) to Laguardia Airport (LGA) flights

Calendar54Weekly Planes
Duration2h 10mAverage Duration
Ticket$132Cheapest Price
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Questions & Answers

Map of how to get from Chicago Union Station to Enterprise Rent a Car.ExpandLaunch map view
  • Distance: 805.6 mi
  • Duration: 8h 30m

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

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 23h 42m. Alternatively, 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 15m.

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