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How to get fromSan Juan to Chicagoby plane, car, or train

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There are 5 ways to get from San Juan to Chicago by plane, car, or train

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 Luis Munoz Marin International Airport to Chicago Midway International Airport

    best
    1. Fly from Luis Munoz Marin International Airport (SJU) to Chicago Midway International Airport (MDW)plane plane SJU - MDW
    7h 56m
    $177–630

  2. Drive to Eugenio María De Hostos Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Drive from San Juan to Eugenio María De Hostos Airport (MAZ)car car
    2. Fly from Eugenio María De Hostos Airport (MAZ) to Chicago O'Hare International Airport (ORD)plane plane MAZ - ORD
    10h 30m
    $109–400

  3. Fly Luis Munoz Marin International Airport to Chicago O'Hare International Airport

    1. Fly from Luis Munoz Marin International Airport (SJU) to Chicago O'Hare International Airport (ORD)plane plane SJU - ORD
    8h 16m
    $152–480

  4. Fly Isla Grande Airport to Chicago O'Hare International Airport

    1. Fly from Isla Grande Airport (SIG) to Chicago O'Hare International Airport (ORD)plane plane SIG - ORD
    8h 38m
    $127–513

  5. Fly Luis Munoz Marin International Airport to South Bend, train

    1. Fly from Luis Munoz Marin International Airport (SJU) to South Bend (SBN)plane plane SJU - SBN
    2. Take the train from South Bend Airport to Van Buren St.train train
    11h 42m
    $189–642

Luis Munoz Marin International Airport (SJU) to Chicago Midway International Airport (MDW) flights

Calendar30Weekly Planes
Duration8h 5mAverage Duration
Ticket$123Cheapest Price
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Comparing Your Travel Options

Map of how to get from San Juan to Chicago.ExpandLaunch map view
  • Distance: 2,077.8 mi
  • Duration: 7h 56m

What companies run services between San Juan, Puerto Rico and Chicago, IL, USA?

Southwest Airlines, Frontier Airlines, and Delta fly from Luis Munoz Marin International Airport (SJU) to Chicago Midway International Airport (MDW) 4 times a day.

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