SJO - MDW

$267 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
$409
Typical prices: $465-$698
Delta
Fri 1/19Tue 1/30
SJO - MDW • 1 stop
Cheapest one-way
$267
Typical prices: $272-$397
Southwest
Sat 11/17
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 44% compared to booking last minute.
Insights
Insights
When to travel
September
Cheapest • 17% price drop
September
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Houston Hobby (HOU)
Cheapest • Avg $598 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 7h 50m (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, Jan 21 - Sat, Jan 30
Delta Logo
2:23 pm - 11:55 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 32m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 12:58 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
6h 58m1 stop Atlanta Hartsfield-Jackson
$409Delta
Fri, Jan 22 - Sat, Jan 30
Delta Logo
7:00 am - 9:16 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
26h 16m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 12:58 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
6h 58m1 stop Atlanta Hartsfield-Jackson
$409Delta
Fri, Jan 22 - Sat, Jan 30
Delta Logo
7:00 am - 11:55 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
16h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 12:58 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
6h 58m1 stop Atlanta Hartsfield-Jackson
$409Delta
Tue, Jan 19 - Sat, Jan 30
Delta Logo
7:00 am - 11:55 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
16h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 12:58 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
6h 58m1 stop Atlanta Hartsfield-Jackson
$409Delta
Sat, Feb 6 - Tue, Feb 16
Delta Logo
3:55 pm - 11:55 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:33 am - 10:05 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
12h 32m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$430Delta
Sat, Feb 6 - Tue, Feb 16
Delta Logo
3:55 pm - 11:55 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:50 am - 10:05 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
11h 15m1 stop Atlanta Hartsfield-Jackson
$430Delta
Tue, Dec 22 - Fri, Jan 8
Delta Logo
2:24 pm - 8:49 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
18h 25m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 9:49 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
15h 49m1 stop Atlanta Hartsfield-Jackson
$459Delta
Sat, Dec 26 - Fri, Jan 8
Delta Logo
3:55 pm - 9:13 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
17h 18m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 9:49 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
15h 49m1 stop Atlanta Hartsfield-Jackson
$459Delta
Thu, Feb 18 - Wed, Feb 24
Southwest Logo
1:05 pm - 12:10 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
11h 05m1 stop Houston Hobby
Southwest Logo
5:20 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 25m1 stop Houston Hobby
$517Southwest
Fri, Jan 15 - Sun, Jan 24
Southwest Logo
1:50 pm - 11:00 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 10m1 stop Baltimore/Washington
Southwest Logo
5:20 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 25m1 stop Houston Hobby
$520Southwest
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 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 typically range from $465 to $698. The lowest price found in the past 5 days was $409, on Delta.

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

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from San José to Chicago Midway Airport. It’s 15% cheaper than the average day, while Sunday is the most expensive, with prices 9% higher.

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

•September is the cheapest month to fly from San José to Chicago Midway Airport at $476 round-trip.
•March ($1,078) and July ($831) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 126% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights 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 44% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Key details for San José to Chicago Midway Airport flights

Low season

February

Cheapest flight

$267
Beat the crowds with an average 85% drop in travelers.
The most popular month to fly with an average 157% increase in travelers.
One-way 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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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 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 $465 to $698, with an average of $571 over the past 12 months. Anything below $465 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 two weeks of departure) run 36% above the $571 route average. Book 11 weeks before departure for the lowest fares.

  • 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 $281, which is 16% 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 averaging $84 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) - 48% of one-stop connections
    • Houston Hobby (HOU) - 31% of one-stop connections
    • Orlando (MCO) - 21% of one-stop connections

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

    Yes. Flexible dates can save you up to 22% on flights from San José to Chicago Midway Airport. Wednesday is the cheapest departure day at $489 round-trip on average, while Sunday is the most expensive at $623, a difference of $134.

    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 50m, compared with 8h 11m via Orlando (MCO) and 8h 14m via Houston Hobby (HOU).

  • 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 Soldier Field. 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 are flexible, aim for a Wednesday departure and avoid flying on Sunday. On this route, Wednesday flights average $489, about $134 less than Sunday fares (22% 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 44% 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 September. Fares historically average $476 round-trip in that month - typically $602 less than the most expensive month, which is March (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 Chicago Midway Airport

More options for your flight from San José to Midway

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