SJC - MDW

$155 Find Cheap Flights from San Jose to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$333
Typical prices: $391-$579
Delta
Tue 2/13Sun 2/18
SJC - MDW • 2 stops
Cheapest non-stop
$349
Typical prices: $387-$567
Southwest
Mon 12/3Wed 12/5
SJC - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 4h 04m
Direct flights
+1
Direct flights
+1
When to book
15 weeks
in advance
Our data shows that travelers who book at least 15 weeks in advance save around 68% compared to booking last minute.
Insights
Insights
When to travel
August
Cheapest • 16% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Long Beach Municipal (LGB)
Cheapest • Avg $430 (round-trip)
Denver Intl (DEN)
Shortest trip • 6h 11m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!

Cheap Flights from San Jose to Midway (SJC-MDW)

 

Cheap flights from San Jose to Midway with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Sat, Feb 13 - Mon, Feb 22
Delta Logo
1:50 pm - 8:49 amSJC  San Jose-MDW Chicago Midway
16h 59m2 stops Los Angeles Minneapolis St Paul
Delta Logo
1:00 pm - 12:54 pmMDW  Chicago Midway-SJC San Jose
25h 54m2 stops Detroit Metropolitan Wayne County Los Angeles
$333Delta
Sat, Feb 13 - Fri, Feb 19
Delta Logo
1:50 pm - 8:49 amSJC  San Jose-MDW Chicago Midway
16h 59m2 stops Los Angeles Minneapolis St Paul
Delta Logo
1:00 pm - 8:17 amMDW  Chicago Midway-SJC San Jose
21h 17m2 stops Detroit Metropolitan Wayne County Los Angeles
$333Delta
Sat, Feb 13 - Thu, Feb 18
Delta Logo
1:50 pm - 8:49 amSJC  San Jose-MDW Chicago Midway
16h 59m2 stops Los Angeles Minneapolis St Paul
Delta Logo
1:00 pm - 12:54 pmMDW  Chicago Midway-SJC San Jose
25h 54m2 stops Detroit Metropolitan Wayne County Los Angeles
$333Delta
Wed, Dec 2 - Sat, Dec 5
Southwest Logo
11:10 am - 5:15 pmSJC  San Jose-MDW Chicago Midway
4h 05mnonstop
Southwest Logo
6:10 pm - 8:55 pmMDW  Chicago Midway-SJC San Jose
4h 45mnonstop
$349Southwest
Thu, Nov 5 - Wed, Nov 11
Southwest Logo
11:00 pm - 5:00 amSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
10:10 am - 12:55 pmMDW  Chicago Midway-SJC San Jose
4h 45mnonstop
$349Southwest
Fri, Dec 11 - Mon, Dec 14
Southwest Logo
11:50 am - 5:50 pmSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
3:50 pm - 6:30 pmMDW  Chicago Midway-SJC San Jose
4h 40mnonstop
$349Southwest
Thu, Nov 26 - Thu, Dec 3
Southwest Logo
6:45 am - 12:45 pmSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
3:50 pm - 6:30 pmMDW  Chicago Midway-SJC San Jose
4h 40mnonstop
$349Southwest
Thu, Dec 3 - Sat, Dec 5
Southwest Logo
11:10 am - 5:15 pmSJC  San Jose-MDW Chicago Midway
4h 05mnonstop
Southwest Logo
6:10 pm - 8:55 pmMDW  Chicago Midway-SJC San Jose
4h 45mnonstop
$349Southwest
Thu, Nov 5 - Wed, Nov 11
Southwest Logo
11:00 pm - 5:00 amSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
10:10 am - 12:55 pmMDW  Chicago Midway-SJC San Jose
4h 45mnonstop
$349Southwest
Fri, Nov 27 - Fri, Dec 4
Southwest Logo
11:00 pm - 5:00 amSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
3:50 pm - 6:30 pmMDW  Chicago Midway-SJC San Jose
4h 40mnonstop
$349Southwest

Price, demand and travel trends for San Jose 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 Jose to Chicago Midway Airport?

Round-trip flights from San Jose to Chicago Midway Airport typically range from $391 to $579. The lowest price found in the past 5 days was $333, on Delta.

What's the cheapest day of the week to fly from San Jose 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 Jose to Chicago Midway Airport. It’s 12% cheaper than the average day, while Sunday is the most expensive, with prices 60% higher.

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

•August is the cheapest month to fly from San Jose to Chicago Midway Airport at $407 round-trip.
•January ($597) and June ($551) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 46% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from San Jose to Chicago Midway Airport the cheapest?

Flights from San Jose to Chicago Midway Airport are cheapest 15 weeks before departure. Booking in this window typically costs about 68% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Expert advice for your flight from San Jose to Midway

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Bill Fink

Bill Fink

Expert on SJC

Bill is an award-winning travel writer with extensive credits covering airlines and the aviation industry for publications including AARP, AFAR, The Points Guy and Yahoo. Based in Portland, Oregon, Bill has traveled to more than 75 countries - and been late for his flight in most of them. He once achieved top-level frequent flier status for all of American, Delta and United Airlines during a single year.

Read more

Key details for San Jose to Chicago Midway Airport flights

Low season

February

Cheapest flight

$155
Beat the crowds with an average 56% drop in travelers.
The most popular month to fly with an average 52% increase in travelers.
One-way flight from San Jose to Chicago Midway Airport

When to book flights from San Jose to Midway

Are your dates flexible? Find out the best times to travel from San Jose 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 Jose to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from San Jose to Chicago Midway Airport?

    These are the earliest and latest flight times available from San Jose to Chicago Midway Airport:

    • Earliest: departs at 6:00 am and lands at 10:04 am
    • Latest: departs at 11:00 pm and lands at 3:04 am.

    The flight takes about 4h 04m.

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

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

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

    A nonstop flight from San Jose to Chicago Midway Airport takes 4h 04m, covering 1,832 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

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

    Round-trip flights from San Jose to Chicago Midway Airport range from $391 to $579, with an average of $483 over the past 12 months. Anything below $391 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 113% above the $483 route average. Book 15 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from San Jose to Chicago Midway Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $430 round-trip via Long Beach Municipal (LGB), compared to $473 for nonstop.

  • What is the standard checked-bag allowance on flights from San Jose to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from San Jose to Chicago Midway Airport?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest and United Airlines. Other aircraft seen on the route include Boeing 737-800 variants.

  • How are flight departures from San Jose to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on San Jose to Chicago Midway Airport flights, with 50% of flights leaving in that window. Night departures account for 50%, afternoon flights for 0%, and evening flights for 0%.

  • Have flight prices from San Jose 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 $333 to $2,068. That means the highest observed fare was about 6x higher than the lowest one.

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

    One-way fares from San Jose to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $164, which is 44% 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 Jose to Chicago Midway Airport?

    Flights from San Jose to Chicago Midway Airport usually depart from San Jose (SJC) and arrive at Chicago Midway (MDW).

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

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

    • Denver Intl (DEN) - 50% of one-stop connections
    • Las Vegas Harry Reid Intl (LAS) - 21% of one-stop connections
    • Phoenix Sky Harbor Intl (PHX) - 14% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 7% of one-stop connections

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

    Yes. Flexible dates can save you up to 45% on flights from San Jose to Chicago Midway Airport. Wednesday is the cheapest departure day at $427 round-trip on average, while Sunday is the most expensive at $776, a difference of $349.

    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 airlines fly from San Jose to Chicago Midway Airport?

    Only Southwest operates flights between San Jose and Chicago Midway Airport.

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

    Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 6h 11m, compared with 6h 27m via Las Vegas Harry Reid Intl (LAS) and 6h 29m via Phoenix Sky Harbor Intl (PHX).

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

    Chicago Midway Airport is 2 hours ahead of San Jose (Central Time vs Pacific 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 Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on San Jose to Chicago Midway Airport flights?

    Among airlines operating San Jose to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on San Jose to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking San Jose 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 $427, about $349 less than Sunday fares (45% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 15 weeks before you fly. On this route, that window historically saves about 68% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your San Jose to Chicago Midway Airport trip for August. Fares historically average $407 round-trip in that month - typically $190 less than the most expensive month, which is January (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Long Beach Municipal Airport (LGB) can be cheaper than flying direct. The cheapest layover option averages $430 round-trip on this route - about $43 less than direct flights (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

Prefer to fly direct from San Jose to Chicago Midway Airport?

 
Find which airlines fly direct from San Jose Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

San Jose to Chicago Midway

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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Direct returns

Chicago Midway to San Jose

Monday

Southwest

Southwest

Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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More options for your flight from San Jose to Midway

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

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