MDW - SJO

$290 Find Cheap Flights from Chicago Midway Airport to San José - Compare and Save

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Everything you should know

Cheapest round-trip
$439
Typical prices: $532-$794
Delta
Sun 1/21Sun 1/28
MDW - SJO • 1 stop
Cheapest one-way
$290
Typical prices: $244-$324
Multiple Airlines
Fri 2/2
MDW - SJO • 2 stops
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 • 42% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Houston Hobby (HOU)
Cheapest • Avg $635 (round-trip)
Orlando (MCO)
Shortest trip • 7h 59m (one-way)
Insights
Insights
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We hope you love your trip to San José!
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 21 - Thu, Jan 28
Delta Logo
6:00 am - 9:49 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
15h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 11:55 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
16h 55m1 stop Atlanta Hartsfield-Jackson
$439Delta
Thu, Jan 21 - Thu, Jan 28
Delta Logo
6:00 am - 9:49 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
15h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:23 pm - 6:00 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
27h 37m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$443Delta
Sat, Nov 14 - Sat, Nov 21
KLM Logo
11:27 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
10h 48m1 stop Atlanta Hartsfield-Jackson
KLM Logo
7:00 am - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
15h 54m1 stop Atlanta Hartsfield-Jackson
$454KLM
Sat, Nov 14 - Sat, Nov 21
Delta Logo
9:30 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
12h 45m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
15h 54m1 stop Atlanta Hartsfield-Jackson
$465Delta
Sat, Nov 14 - Tue, Nov 17
Delta Logo
11:27 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
10h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 4:18 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 18m1 stop Atlanta Hartsfield-Jackson
$473Delta
Sat, Nov 14 - Fri, Nov 20
Delta Logo
11:27 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
10h 48m1 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
$473Delta
Sat, Nov 14 - Wed, Nov 18
Delta Logo
11:27 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
10h 48m1 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
$473Delta
Thu, Feb 25 - Thu, Mar 4
Southwest Logo
5:20 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 25m1 stop Houston Hobby
Southwest Logo
1:05 pm - 12:10 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
11h 05m1 stop Houston Hobby
$497Southwest
Thu, Feb 25 - Thu, Mar 4
Southwest Logo
5:20 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 25m1 stop Houston Hobby
Southwest Logo
1:50 pm - 8:55 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
19h 05m2 stops Baltimore/Washington Orlando
$502Southwest
Sun, Feb 7 - Thu, Feb 18
Southwest Logo
5:05 am - 12:50 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
7h 45m1 stop Orlando
Southwest Logo
1:50 pm - 11:00 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 10m1 stop Baltimore/Washington
$514Southwest
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 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 typically range from $532 to $794. The lowest price found in the past 5 days was $439, on Delta.

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

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Chicago Midway Airport to San José. It’s 20% cheaper than the average day, while Saturday is the most expensive, with prices 14% higher.

What’s 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 July ($740) 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

$290
Beat the crowds with an average 41% drop in travelers.
The most popular month to fly with an average 32% increase in travelers.
One-way 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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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.

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

    A nonstop flight from Chicago Midway Airport to San José takes 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.

  • 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 $532 to $794, with an average of $666 over the past 12 months. Anything below $532 counts as a good deal.

  • 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 $439 to $3,055. That means the highest observed fare was about 7x 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 higher than usual. Average one-way flight prices are about $310, which is 6% above the typical average for this route.

  • 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 averaging $30 for economy cars. Top options include:

    • Priceless
    • Avis
    • Budget
    • Alamo
    • Payless

  • 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).

  • 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:

    • Houston Hobby (HOU) - 39% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 38% of one-stop connections
    • Orlando (MCO) - 23% of one-stop connections

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

    Yes. Flexible dates can save you up to 30% on flights from Chicago Midway Airport to San José. Wednesday is the cheapest departure day at $535 round-trip on average, while Saturday is the most expensive at $762, a difference of $227.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

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

    Flying via Orlando (MCO) gives the shortest average 1-stop total travel time at 7h 59m, compared with 8h via Atlanta Hartsfield-Jackson (ATL) and 8h 10m via Houston Hobby (HOU).

  • 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.

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 are flexible, aim for a Wednesday departure and avoid flying on Saturday. On this route, Wednesday flights average $535, about $227 less than Saturday fares (30% 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