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MDW - SJC

$90 Find cheap flights from Chicago Midway Airport to San Jose

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to San Jose departing on 8/31. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/29
Sat 7/6

Search hundreds of travel sites at once for deals on flights to San Jose

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Jose, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Jose, as well as popular online travel agencies
In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

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Cheap flight deals from Midway to San Jose (MDW-SJC)

 
These are the cheapest deals for flights from Midway to San Jose currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to San Jose

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to San Jose.

Recent one-way flight deals from Midway to San Jose

Only flying one-way? Below are some of the best one-way flight deals from Midway to San Jose found on KAYAK recently.

Recent last minute flight deals from Midway to San Jose

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Midway to San Jose.

Recent direct flight deals from Midway to San Jose

The latest deals for direct flights from Midway to San Jose so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Midway to San Jose

Find recent round-trip train or bus tickets from Midway to San Jose.

All round-trip flight deals to San Jose

The cheapest plane tickets to San Jose found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:32 am - 6:06 pmMDW-SJC
8h 34m1 stop
10:20 pm - 6:33 amSJC-MDW
6h 13m1 stop
$180Frontier
Find Deal
Sat, Sep 14 - Tue, Sep 17
6:00 am - 5:23 pmMDW-SJC
13h 23m1 stop
10:20 pm - 6:33 amSJC-MDW
6h 13m1 stop
$181Frontier
Find Deal
Thu, Aug 29 - Mon, Sep 2
11:32 am - 6:06 pmMDW-SJC
8h 34m1 stop
10:20 pm - 6:33 amSJC-MDW
6h 13m1 stop
$188Frontier
Find Deal
Thu, Sep 19 - Tue, Sep 24
6:15 am - 5:45 pmMDW-SJC
13h 30m1 stop
10:20 pm - 6:33 amSJC-MDW
6h 13m1 stop
$198Frontier
Find Deal
Wed, Aug 7 - Sat, Aug 24
9:29 am - 4:19 pmMDW-SJC
8h 50m2 stops
6:15 am - 2:09 pmSJC-MDW
5h 54m1 stop
$345Delta
Find Deal
Tue, Jul 2 - Tue, Jul 23
2:49 pm - 8:31 pmMDW-SJC
7h 42m1 stop
6:15 am - 2:09 pmSJC-MDW
5h 54m1 stop
$372Delta
Find Deal
Fri, Jul 19 - Tue, Jul 23
9:08 pm - 11:59 pmMDW-SJC
28h 51m3 stops
5:27 pm - 9:47 amSJC-MDW
14h 20m1 stop
$778
Find Deal
Fri, Jun 28 - Mon, Jul 1
8:13 pm - 11:15 pmMDW-SJC
29h 02m3 stops
7:00 am - 9:47 amSJC-MDW
24h 47m2 stops
$834
Find Deal
Thu, Aug 29 - Mon, Sep 2
8:50 pm - 9:02 amMDW-SJC
14h 12m1 stop
1:24 pm - 9:47 amSJC-MDW
18h 23m1 stop
$866Volaris
Find Deal
Wed, Jun 26 - Wed, Jul 3
8:45 pm - 9:02 amMDW-SJC
14h 17m1 stop
1:34 pm - 9:52 amSJC-MDW
18h 18m1 stop
$933Volaris
Find Deal
Tue, Jun 25 - Tue, Jul 2
11:32 am - 6:06 pmMDW-SJC
8h 34m1 stop
$90Frontier
Find Deal
Sat, Aug 31
8:58 pm - 8:24 amMDW-SJC
13h 26m1 stop
$96
Find Deal
Mon, Jun 10
6:00 am - 5:45 pmMDW-SJC
13h 45m1 stop
$100Frontier
Find Deal
Tue, Aug 13
6:00 am - 5:23 pmMDW-SJC
13h 23m1 stop
$102Frontier
Find Deal
Thu, Sep 26
6:15 am - 4:57 pmMDW-SJC
12h 42m1 stop
$114Frontier
Find Deal
Mon, Aug 12
9:48 am - 5:41 pmMDW-SJC
9h 53m1 stop
$116Frontier
Find Deal
Fri, Aug 9
3:45 pm - 9:43 pmMDW-SJC
7h 58m1 stop
$154Delta
Find Deal
Tue, Sep 24
10:28 am - 7:33 pmMDW-SJC
11h 05m2 stops
$159Delta
Find Deal
Wed, Aug 14
12:35 pm - 8:39 pmMDW-SJC
10h 04m2 stops
$179Delta
Find Deal
Sat, Aug 31
8:50 pm - 9:02 amMDW-SJC
14h 12m1 stop
$368Volaris
Find Deal
Wed, Jun 26
3:45 pm - 10:45 pmMDW-SJC
9h 00m1 stop
6:37 am - 3:50 pmSJC-MDW
7h 13m1 stop
$822Delta
Find Deal
Sat, Jun 1 - Wed, Jun 5
11:01 am - 7:13 pmMDW-SJC
10h 12m2 stops
6:37 am - 3:50 pmSJC-MDW
7h 13m1 stop
$827Delta
Find Deal
Sat, Jun 1 - Wed, Jun 5
4:41 pm - 10:45 pmMDW-SJC
8h 04m1 stop
5:00 pm - 8:48 amSJC-MDW
13h 48m2 stops
$978Delta
Find Deal
Tue, Jun 4 - Sat, Jun 29
9:46 am - 7:13 pmMDW-SJC
11h 27m2 stops
5:00 pm - 8:48 amSJC-MDW
13h 48m2 stops
$983Delta
Find Deal
Tue, Jun 4 - Sat, Jun 29
3:45 pm - 10:45 pmMDW-SJC
9h 00m1 stop
12:26 pm - 9:48 pmSJC-MDW
7h 22m1 stop
$1,038Delta
Find Deal
Sun, Jun 2 - Sat, Jun 8
1:21 pm - 8:33 pmMDW-SJC
9h 12m2 stops
12:26 pm - 9:48 pmSJC-MDW
7h 22m1 stop
$1,103Delta
Find Deal
Sun, Jun 2 - Sat, Jun 8
9:32 am - 7:13 pmMDW-SJC
11h 41m2 stops
7:56 pm - 9:06 amSJC-MDW
11h 10m2 stops
$1,178Delta
Find Deal
Sat, Jun 1 - Wed, Jun 5
6:00 am - 4:14 pmMDW-SJC
12h 14m2 stops
6:00 am - 6:30 pmSJC-MDW
10h 30m2 stops
$1,183Delta
Find Deal
Sat, Jun 1 - Sat, Jun 22
11:01 am - 7:54 pmMDW-SJC
10h 53m1 stop
12:26 pm - 9:46 pmSJC-MDW
7h 20m1 stop
$1,253Delta
Find Deal
Sat, Jun 1 - Sat, Jun 22

Flights from Midway to San Jose - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to San Jose to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to San Jose?

The average price of all flights from Chicago Midway Airport to San Jose clicked on KAYAK for each day over the last 12 months.
When flying from Chicago Midway Airport to San Jose, you should consider leaving on a Monday and avoid Saturdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Saturdays and the most expensive ones on Sundays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to San Jose, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to San Jose is April, where tickets cost $308 on average. On the other hand, the most expensive months are November and January, where the average cost of tickets is $517 and $490 respectively.

How far in advance should I book a flight from Chicago Midway Airport to San Jose?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to San Jose, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to San Jose, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 17 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to San Jose?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Frontier offered the best one-way deal for that route, at $90. KAYAK users also found Chicago Midway Airport to San Jose round-trip flights on Frontier from $180 and on Delta from $345.

How many flights are there between Chicago Midway Airport and San Jose per day?

Each day, there are between 1 and 3 nonstop flights that take off from Chicago Midway Airport and land in San Jose, with an average flight time of 4h 32m. The most common departure time is 6:00 pm and most flights take off in the morning. Each week, there are 18 flights. The most frequent day of departure is Tuesday, when 17% of all weekly flights depart. The fewest flights depart on a Sunday.

What’s the earliest departure time from Chicago Midway Airport to San Jose?

Early birds can take the earliest flight from Chicago Midway Airport at 8:10 am and will be landing in San Jose at 10:45 am.

What’s the latest departure time from Chicago Midway Airport to San Jose?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to San Jose jets off at 8:15 pm and lands at 10:45 pm.

Good to know

Cheapest flight

$90
Flight from Chicago Midway Airport to San Jose

When to book flights from Midway to San Jose

Are your dates flexible? Find out the best times to travel from Midway to San Jose based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to San Jose flights

  • What is the cheapest flight from Chicago Midway Airport to San Jose?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to San Jose was $90 for a one-way ticket and $180 for a round-trip.

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

    No

  • Which aircraft models fly most regularly from Chicago Midway Airport to San Jose?

    The Boeing 737-700 Passenger/BBJ1 (winglets) is the aircraft model that flies most regularly on the Chicago Midway Airport to San Jose flight route.

  • On which days can I fly direct from Chicago Midway Airport to San Jose?

    There are nonstop flights from Chicago Midway Airport to San Jose on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to San Jose?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to San Jose.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to San Jose?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Jose from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to San Jose?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San Jose with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SJC can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to San Jose?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San Jose from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Chicago Midway Airport to San Jose?

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

Nonstop departures

Chicago Midway to San Jose

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

San Jose to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top airline flying from Midway to San Jose

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Jose. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to San Jose? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10457 reviews
8.6Crew
8.2Boarding
8.0Entertainment
7.9Comfort
7.4Food
Airline reviews

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

8.0 ExcellentLiam, May 2024SLC - SJC
Read more about Delta reviews

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

Bag drop off was slow and annoying. Only 2 agents at the entire delta desk, and no one directing traffic for what line to be in, many confused people slowed down the process. Boarding was fine. Seats in Delta comfort plus were fine. Snacks were great! Definitely a bonus. The entertainment system was awful — old, slow, not responsive, and completely unable to play games due to some kind of error. But on the other hand, thank you to Delta for the free WiFi. That made it better.

Everything was very good other than I had selected a specific seat when I booked the flight and they changed it once I checked-in the day before my flight. I was still in first class but lost my aisle seat for a window seat. Being tall, the aisle offers more comfort so I always select an aisle seat.

Flight diverted in SD. Later take off in Seattle by 1.3hrs

Book cheap flights from Chicago to San Jose

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to San Jose found on KAYAK in the last 72 hours.
8/31Sat
1 stopFrontier
8h 34mMDW-SJC
$90
6/10Mon
1 stop
13h 26mMDW-SJC
$96
8/13Tue
1 stopFrontier
13h 45mMDW-SJC
$100
9/26Thu
1 stopFrontier
13h 23mMDW-SJC
$102
8/12Mon
1 stopFrontier
12h 42mMDW-SJC
$114
8/9Fri
1 stopFrontier
9h 53mMDW-SJC
$116
9/24Tue
1 stopDelta
7h 58mMDW-SJC
$154
8/14Wed
2 stopsDelta
11h 05mMDW-SJC
$159
8/31Sat
2 stopsDelta
10h 04mMDW-SJC
$179
6/26Wed
1 stopVolaris
14h 12mMDW-SJC
$368

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Last minute flights from Midway to San Jose

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to San Jose that are departing in the next 10 days.
6/1Sat
multi-stopDelta
9h 00mMDW-SJC
6/5Wed
multi-stopDelta
7h 13mSJC-MDW
$822
6/1Sat
multi-stopDelta
10h 12mMDW-SJC
6/5Wed
multi-stopDelta
7h 13mSJC-MDW
$827
6/4Tue
multi-stopDelta
8h 04mMDW-SJC
6/29Sat
multi-stopDelta
13h 48mSJC-MDW
$978
6/4Tue
multi-stopDelta
11h 27mMDW-SJC
6/29Sat
multi-stopDelta
13h 48mSJC-MDW
$983
6/2Sun
multi-stopDelta
9h 00mMDW-SJC
6/8Sat
multi-stopDelta
7h 22mSJC-MDW
$1,038
6/2Sun
multi-stopDelta
9h 12mMDW-SJC
6/8Sat
multi-stopDelta
7h 22mSJC-MDW
$1,103
6/1Sat
multi-stopDelta
11h 41mMDW-SJC
6/5Wed
multi-stopDelta
11h 10mSJC-MDW
$1,178
6/1Sat
multi-stopDelta
12h 14mMDW-SJC
6/22Sat
multi-stopDelta
10h 30mSJC-MDW
$1,183
6/1Sat
multi-stopDelta
10h 53mMDW-SJC
6/22Sat
multi-stopDelta
7h 20mSJC-MDW
$1,253

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Chicago Midway Airport - San Jose Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

San Jose (SJC)United States

Return flight deals:

San Jose - Chicago Midway Airport

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