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MDW - SJC

$159 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 6/11. 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
Tue 6/11
Tue 6/18

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 42,369,914 times on KAYAK, and here is why:

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to San Jose that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
2:25 pm - 8:37 pmMDW-SJC
8h 12m1 stop
12:05 pm - 9:47 pmSJC-MDW
7h 42m1 stop
$308Delta
Find Deal
Wed, Jul 24 - Wed, Aug 7
2:25 pm - 8:37 pmMDW-SJC
8h 12m1 stop
10:15 pm - 1:05 pmSJC-MDW
12h 50m2 stops
$377Delta
Find Deal
Thu, Jul 11 - Mon, Jul 15
2:25 pm - 8:37 pmMDW-SJC
8h 12m1 stop
7:37 pm - 8:37 amSJC-MDW
11h 00m2 stops
$398Delta
Find Deal
Wed, Jul 24 - Wed, Aug 7
1:05 pm - 7:08 pmMDW-SJC
8h 03m1 stop
10:55 pm - 9:17 amSJC-MDW
8h 22m1 stop
$413Delta
Find Deal
Fri, Sep 13 - Mon, Sep 16
3:45 pm - 9:43 pmMDW-SJC
7h 58m1 stop
10:55 pm - 12:31 pmSJC-MDW
11h 36m2 stops
$415Delta
Find Deal
Thu, Sep 26 - Mon, Oct 7
2:00 pm - 8:39 pmMDW-SJC
8h 39m1 stop
6:30 am - 6:05 pmSJC-MDW
9h 35m2 stops
$418Delta
Find Deal
Fri, Sep 13 - Mon, Sep 16
1:10 pm - 10:32 pmMDW-SJC
11h 22m2 stops
10:55 pm - 12:31 pmSJC-MDW
11h 36m2 stops
$420Delta
Find Deal
Thu, Sep 26 - Mon, Oct 7
1:10 pm - 10:32 pmMDW-SJC
11h 22m2 stops
6:30 am - 6:05 pmSJC-MDW
9h 35m2 stops
$423Delta
Find Deal
Fri, Sep 13 - Mon, Sep 16
8:34 am - 9:16 amMDW-SJC
26h 42m3 stops
10:31 am - 6:07 pmSJC-MDW
29h 36m3 stops
$644
Find Deal
Fri, May 24 - Tue, May 28
8:45 pm - 9:02 amMDW-SJC
14h 17m1 stop
5:27 pm - 9:47 amSJC-MDW
14h 20m1 stop
$1,042Volaris
Find Deal
Sat, Jun 29 - Fri, Jul 5

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 Tuesdays.

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, Delta offered the best one-way deal for that route, at $159. KAYAK users also found Chicago Midway Airport to San Jose round-trip flights on Delta from $308 and on Volaris from $1,042.

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

Each day, there are between 2 and 5 nonstop flights that take off from Chicago Midway Airport and land in San Jose, with an average flight time of 4h 34m. The most common departure time is 4:00 pm and most flights take off in the afternoon. Each week, there are 30 flights. The most frequent day of departure is Monday, 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 8:20 am and will be landing in San Jose at 10:55 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

$159
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 $159 for a one-way ticket and $308 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 10751 reviews
8.0Entertainment
8.6Crew
8.2Boarding
7.9Comfort
7.4Food
Airline reviews

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

6.0 GoodEliza, Apr 2024SAN - LAX
Read more about Delta reviews

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

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Crew was not friendly when I went to request a seat change.

Really impressive staff at airport and on plane, especially given how busy it was

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.
6/11Tue
2 stopsDelta
10h 46mMDW-SJC
$159
8/31Sat
2 stopsDelta
10h 21mMDW-SJC
$161
6/11Tue
1 stopDelta
8h 13mMDW-SJC
$186
6/4Tue
1 stopDelta
8h 18mMDW-SJC
$189
6/7Fri
1 stopDelta
8h 13mMDW-SJC
$199
6/10Mon
2 stops
22h 21mMDW-SJC
$204
5/20Mon
1 stopVolaris
14h 17mMDW-SJC
$340
8/4Sun
3 stops
41h 41mMDW-SJC
$365
5/22Wed
1 stopVolaris
17h 28mMDW-SJC
$407
8/4Sun
1 stopFrontier
14h 17mMDW-SJC
$496

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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.
5/13Mon
multi-stop
14h 17mMDW-SJC
5/19Sun
multi-stop
24h 02mSJC-MDW
$925
5/16Thu
multi-stopDelta
8h 18mMDW-SJC
5/18Sat
multi-stopDelta
8h 40mSJC-MDW
$945
5/16Thu
multi-stopDelta
11h 28mMDW-SJC
5/18Sat
multi-stopDelta
8h 40mSJC-MDW
$950
5/16Thu
multi-stopDelta
11h 28mMDW-SJC
5/18Sat
multi-stopDelta
7h 55mSJC-MDW
$955
5/16Thu
multi-stopVolaris
14h 17mMDW-SJC
5/18Sat
multi-stopVolaris
18h 13mSJC-MDW
$965
5/15Wed
multi-stopDelta
10h 02mMDW-SJC
5/18Sat
multi-stopDelta
12h 18mSJC-MDW
$1,053
5/14Tue
multi-stopDelta
8h 18mMDW-SJC
5/15Wed
multi-stopDelta
7h 38mSJC-MDW
$1,088
5/14Tue
multi-stopDelta
10h 53mMDW-SJC
5/15Wed
multi-stopDelta
7h 13mSJC-MDW
$1,093
5/16Thu
multi-stop
27h 09mMDW-SJC
5/18Sat
multi-stop
23h 27mSJC-MDW
$1,113
5/14Tue
multi-stopDelta
14h 08mMDW-SJC
5/15Wed
multi-stopDelta
17h 26mSJC-MDW
$1,125

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Chicago Midway Airport - San Jose Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

San Jose (SJC)United States

Return flight deals:

San Jose - Chicago Midway Airport

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