SJO - MDW

$257 Find Cheap Flights from San José to Chicago Midway Airport - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$437
Typical prices: $435-$615
Delta
Mon 10/29Thu 11/15
SJO - MDW • 1 stop
Cheapest one-way
$257
Typical prices: $272-$380
Southwest
Mon 10/22
SJO - MDW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between San José and Chicago Midway Airport. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to book
11 weeks
in advance
Our data shows that travelers who book at least 11 weeks in advance save around 33% compared to booking last minute.
Insights
Insights
When to travel
January
Cheapest • 33% price drop
September
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Houston Hobby (HOU)
Cheapest • Avg $541 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 7h 47m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Flight Deals

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

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

Recent round-trip flight deals from San José to Midway

Thu, Nov 12 - Tue, Nov 17
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:05 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
9h 10m1 stop Atlanta Hartsfield-Jackson
$437Delta
Mon, Nov 16 - Thu, Dec 10
Delta Logo
7:00 am - 4:18 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 18m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:02 pm - 10:17 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
9h 15m1 stop Atlanta Hartsfield-Jackson
$437Delta
Tue, Nov 3 - Wed, Nov 11
Delta Logo
2:25 pm - 10:33 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 08m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:05 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
9h 10m1 stop Atlanta Hartsfield-Jackson
$437Delta
Thu, Nov 12 - Tue, Nov 17
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
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
$437Delta
Thu, Oct 29 - Sun, Nov 15
Delta Logo
1:25 pm - 10:33 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 08m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
16h 15m1 stop Atlanta Hartsfield-Jackson
$437Delta
Thu, Nov 12 - Mon, Nov 16
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:31 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 44m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$437Delta
Thu, Nov 12 - Mon, Nov 16
Delta Logo
7:00 am - 6:04 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
11h 04m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
1:31 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 44m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$437Delta
Thu, Nov 5 - Sun, Nov 8
Southwest Logo
1:20 pm - 11:00 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 40m1 stop Orlando
Southwest Logo
5:15 am - 12:20 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
7h 05m1 stop Houston Hobby
$462Southwest
Wed, Jan 27 - Tue, Feb 2
Southwest Logo
1:50 pm - 10:50 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 00m1 stop Orlando
Southwest Logo
5:25 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 20m1 stop Houston Hobby
$462Southwest
Thu, Nov 5 - Sun, Nov 8
Southwest Logo
1:20 pm - 12:10 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
10h 50m2 stops Orlando Nashville Intl
Southwest Logo
5:15 am - 12:20 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
7h 05m1 stop Houston Hobby
$466Southwest
Booking Insights

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

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

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

Round-trip flights from San José to Chicago Midway Airport start at $437. Prices are typical for this route right now, with typical round-trip fares ranging from $435 to $615. The lowest price found in the past 5 days was $437 on Delta.

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

Wednesday is the cheapest day of the week to fly from San José to Chicago Midway Airport, it is 8% cheaper than the average day. Sunday is the most expensive day with flight prices 30% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

•January is the cheapest month to fly from San José to Chicago Midway Airport at $342 round-trip.
•July ($831) and June ($734) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 142% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from San José to Chicago Midway Airport the cheapest?

Flights from San José to Chicago Midway Airport are cheapest 11 weeks before departure. Booking in this window typically costs about 33% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

Key details for San José to Chicago Midway Airport flights

Low season

February

Cheapest flight

$257
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from San José to Chicago Midway Airport

When to book flights from San José to Midway

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

Your San José to Chicago Midway Airport flight questions, answered

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

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

    Two cabin classes are available on flights from San José to Chicago Midway Airport:

    • Economy Class
    • First Class

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

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

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

    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 San José to Chicago Midway Airport flight?

    Round-trip flights from San José to Chicago Midway Airport range from $435 to $615, with an average of $513 over the past 12 months. Anything below $435 counts as a good deal.

  • How expensive are last-minute San José to Chicago Midway Airport flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 28% above the route average of $513. Book 11 weeks before departure for the lowest fares.

  • Have flight prices from San José to Chicago Midway Airport 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 $437 to $2,855. That means the highest observed fare was about 7x higher than the lowest one.

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

    One-way fares from San José to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $293, which is 5% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

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

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

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

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

    • Atlanta Hartsfield-Jackson (ATL) - 37% of one-stop connections
    • Orlando (MCO) - 34% of one-stop connections
    • Houston Hobby (HOU) - 29% 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 San José to Chicago Midway Airport?

    Yes. Being flexible with your travel dates can save you up to 30% on the San José to Chicago Midway Airport route. Wednesday is the cheapest departure day at $474 round-trip on average, while Sunday is the most expensive at $670, a difference of $196. 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 San José to Chicago Midway Airport?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 7h 47m, compared with 8h 08m via Orlando (MCO) and 8h 16m via Houston Hobby (HOU).

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

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

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

Your guide to booking San José to Chicago Midway Airport 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 Wednesday departure instead of Sunday. On this route, Wednesday flights average $474 - about $196 less than Sunday (29% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 11 weeks before you fly. On this route, that window historically saves about 33% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your San José to Chicago Midway Airport trip for January. Fares historically average $342 round-trip in that month - typically $489 less than the most expensive month, which is July (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel

More options for your flight from San José to Midway

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
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