MDW - SJO

$178 Find Cheap Flights from Chicago Midway Airport to San José - Compare and Save

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Everything you should know

Cheapest round-trip
$417
Typical prices: $502-$818
Southwest
Sun 1/28Sun 2/4
MDW - SJO • 1 stop
Cheapest one-way
$178
Typical prices: $221-$352
Southwest
Thu 2/1
MDW - SJO • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Chicago Midway Airport and San José. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
February
Cheapest • 41% price drop
November
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Orlando (MCO)
Cheapest • Avg $584 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 7h 58m (one-way)
Insights
Insights
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to San José (MDW-SJO)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to San José

Thu, Jan 28 - Thu, Feb 4
Southwest Logo
5:25 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 20m1 stop Houston Hobby
Southwest Logo
1:50 pm - 10:50 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 00m1 stop Orlando
$417Southwest
Sun, Nov 15 - Thu, Dec 3
Delta Logo
6:00 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
16h 15m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
$418Delta
Sun, Nov 15 - Wed, Dec 2
Delta Logo
6:00 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
16h 15m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 1:01 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
22h 24m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$423Delta
Tue, Feb 2 - Tue, Feb 9
Southwest Logo
5:25 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 20m1 stop Houston Hobby
Southwest Logo
1:50 pm - 10:50 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 00m1 stop Orlando
$437Southwest
Tue, Jan 26 - Tue, Feb 2
Southwest Logo
5:25 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 20m1 stop Houston Hobby
Southwest Logo
1:50 pm - 10:50 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 00m1 stop Orlando
$447Southwest
Sat, Dec 5 - Tue, Dec 8
Delta Logo
11:28 am - 10:17 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
10h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 4:16 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 16m1 stop Atlanta Hartsfield-Jackson
$465Delta
Wed, Nov 18 - Thu, Dec 3
Delta Logo
6:00 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
16h 15m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
$465Delta
Sat, Dec 5 - Wed, Dec 9
Delta Logo
11:28 am - 10:17 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
10h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
$465Delta
Sat, Oct 24 - Sun, Nov 1
Delta Logo
6:04 am - 12:00 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
6h 56m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:25 pm - 10:33 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 08m1 stop Atlanta Hartsfield-Jackson
$465Delta
Tue, Oct 27 - Wed, Nov 4
Delta Logo
6:04 am - 12:00 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
6h 56m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:25 pm - 10:33 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 08m1 stop Atlanta Hartsfield-Jackson
$465Delta
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to San José flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago Midway Airport to San José with more confidence.

How much is a round-trip flight from Chicago Midway Airport to San José?

Round-trip flights from Chicago Midway Airport to San José start at $417. Prices are below average for this route right now, with typical round-trip fares ranging from $502 to $818. The lowest price found in the past 5 days was $417 on Southwest.

What's the cheapest day of the week to fly from Chicago Midway Airport to San José?

Tuesday is the cheapest day of the week to fly from Chicago Midway Airport to San José, it is 25% cheaper than the average day. Monday is the most expensive day with flight prices 32% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Chicago Midway Airport to San José?

•February is the cheapest month to fly from Chicago Midway Airport to San José at $385 round-trip.
•March ($1,098) and December ($893) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 185% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Chicago Midway Airport to San José flights

Low season

February

Cheapest flight

$178
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly and prices are also 27% lower on average.
Flight from Chicago Midway Airport to San José

When to book flights from Midway to San José

Are your dates flexible? Find out the best times to travel from Midway to San José based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to San José flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Chicago Midway Airport to San José?

    Flights from Chicago Midway Airport to San José usually depart from Chicago Midway (MDW) and arrive at San José Juan Santamaria Intl (SJO).

  • What cabin classes can I book on flights from Chicago Midway Airport to San José?

    Only Economy Class is available on flights from Chicago Midway Airport to San José.

  • Which airports do connecting flights from Chicago Midway Airport to San José pass through?

    One-stop flights from Chicago Midway Airport to San José most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 46% of one-stop connections
    • Houston Hobby (HOU) - 34% of one-stop connections
    • Orlando (MCO) - 20% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to San José?

    Yes. Being flexible with your travel dates can save you up to 43% on the Chicago Midway Airport to San José route. Tuesday is the cheapest departure day at $497 round-trip on average, while Monday is the most expensive at $871, a difference of $374. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What popular places can I visit in San José?

    Some of the most popular sights in San José are Parque Metropolitano La Sabana, Estadio Nacional de Costa Rica and Museo de Oro. These are among the most viewed places in San José on KAYAK.

  • How long is a flight from Chicago Midway Airport to San José?

    A nonstop flight from Chicago Midway Airport to San José takes 0h 00m, covering 2,206 miles.

  • Do I need a passport to fly from Chicago Midway Airport to San José?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • Have flight prices from Chicago Midway Airport to San José changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $417 to $3,273. That means the highest observed fare was about 8x higher than the lowest one.

  • How are flight prices from Chicago Midway Airport to San José looking right now?

    One-way fares from Chicago Midway Airport to San José are currently lower than usual. Average one-way flight prices are about $244, which is 11% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to San José?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 7h 58m, compared with 7h 58m via Orlando (MCO) and 8h 04m via Houston Hobby (HOU).

  • What is the time difference between Chicago Midway Airport and San José?

    San José is 1 hour behind Chicago Midway Airport (Central Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at San José Juan Santamaria Intl Airport (SJO)?

    San José Juan Santamaria Intl Airport (SJO) hosts 5 major car rental companies, with daily rates starting from around $1 for economy cars. Top options include:
    • Budget
    • Avis
    • Priceless
    • Routes Car & Truck Rentals
    • Payless

  • How much should I expect to pay for a Chicago Midway Airport to San José flight?

    Round-trip flights from Chicago Midway Airport to San José range from $502 to $818, with an average of $658 over the past 12 months. Anything below $502 counts as a good deal.

Your guide to booking Chicago Midway Airport to San José flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Tuesday departure instead of Monday. On this route, Tuesday flights average $497 - about $374 less than Monday (43% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago Midway Airport to San José trip for February. Fares historically average $385 round-trip in that month - typically $713 less than the most expensive month, which is March (based on the last 12 months).

More options for your flight from Midway to San José

Complete your trip to San José with a hotel stay or car rental

Car rentals in San José
Hotels in San José
Vacations in San José