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MDW - SJC

Find cheap flights from Chicago Midway Airport to San Jose from $89

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 5/21. 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
Thu 5/16
Thu 5/23

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 43,990,755 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

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
10:59 pm - 11:31 amMDW-SJC
14h 32m2 stops
4:40 pm - 5:50 amSJC-MDW
11h 10m1 stop
Tue, May 14 - Tue, May 21
10:59 pm - 8:41 amMDW-SJC
11h 42m1 stop
5:45 pm - 11:50 pmSJC-MDW
28h 05m1 stop
Tue, May 14 - Tue, May 21
10:12 am - 4:55 pmMDW-SJC
8h 43m1 stop
4:40 pm - 5:50 amSJC-MDW
11h 10m1 stop
Wed, May 15 - Tue, May 21
10:59 pm - 8:41 amMDW-SJC
11h 42m1 stop
7:10 am - 9:38 pmSJC-MDW
12h 28m2 stops
Tue, May 14 - Sat, May 18
10:12 am - 4:55 pmMDW-SJC
8h 43m1 stop
7:10 am - 9:38 pmSJC-MDW
12h 28m2 stops
Wed, May 15 - Sat, May 18
10:59 pm - 9:41 amMDW-SJC
12h 42m1 stop
4:40 pm - 5:50 amSJC-MDW
11h 10m1 stop
Mon, May 13 - Tue, May 21
10:59 pm - 8:41 amMDW-SJC
11h 42m1 stop
7:00 am - 10:03 pmSJC-MDW
13h 03m2 stops
Tue, May 7 - Thu, May 9
10:59 pm - 8:41 amMDW-SJC
11h 42m1 stop
2:16 pm - 11:50 pmSJC-MDW
7h 34m1 stop
Tue, May 14 - Mon, May 20
2:15 pm - 8:33 pmMDW-SJC
8h 18m1 stop
10:20 pm - 7:55 amSJC-MDW
7h 35m1 stop
$362Delta
Find Deal
Fri, May 17 - Sun, May 19
3:45 pm - 9:43 pmMDW-SJC
7h 58m1 stop
7:37 pm - 8:45 amSJC-MDW
11h 08m2 stops
$367Delta
Find Deal
Sat, Sep 14 - Wed, Sep 18

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 Wednesdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Tuesdays and the most expensive ones on Mondays.

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 September, where tickets cost $341 on average. On the other hand, the most expensive months are November and December, where the average cost of tickets is $529 and $475 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 75 days before departure.

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

Each day, there are between 1 and 2 nonstop flights that take off from Chicago Midway Airport and land in San Jose, with an average flight time of 4h 37m. The most common departure time is 4:00 pm and most flights take off in the afternoon. Each week, there are 12 flights. The most frequent day of departure is Wednesday, 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 9:35 am and will be landing in San Jose at 12:15 pm.

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 7:25 pm and lands at 10:00 pm.

Good to know

Low season

May

High season

May

Cheapest flight

$89
Best time to beat the crowds with an average 49% drop in price.
Most popular time to fly and prices are also 49% lower on average.
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 $89 for a one-way ticket and $178 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 11123 reviews
8.2boarding
7.9comfort
8.0entertainment
7.5food
8.6crew
Airline reviews

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

8.0 ExcellentCarisa, Mar 2024DFW - LAX
Read more about Delta reviews

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

Was a great smooth flight from Detroit to San Diego.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

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.
5/21Tue
1 stop
13h 31mMDW-SJC
$89
5/15Wed
1 stop
8h 43mMDW-SJC
$98
4/22Mon
1 stop
10h 16mMDW-SJC
$100
5/17Fri
2 stops
23h 45mMDW-SJC
$112
6/15Sat
1 stopDelta
7h 28mMDW-SJC
$181
6/6Thu
1 stopDelta
8h 18mMDW-SJC
$186
6/18Tue
2 stopsDelta
11h 15mMDW-SJC
$191
5/29Wed
1 stopDelta
8h 04mMDW-SJC
$211
4/22Mon
1 stopVolaris
14h 17mMDW-SJC
$369
4/21Sun
1 stopVolaris
14h 17mMDW-SJC
$423

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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.
4/18Thu
multi-stop
33h 21mMDW-SJC
4/21Sun
multi-stop
19h 52mSJC-MDW
$499
4/18Thu
multi-stop
13h 18mMDW-SJC
4/21Sun
multi-stop
19h 52mSJC-MDW
$643
4/18Thu
multi-stopDelta
8h 57mMDW-SJC
4/23Tue
multi-stopDelta
8h 50mSJC-MDW
$918
4/18Thu
multi-stopDelta
8h 34mMDW-SJC
4/23Tue
multi-stopDelta
7h 50mSJC-MDW
$923
4/19Fri
multi-stopDelta
8h 57mMDW-SJC
4/21Sun
multi-stopDelta
9h 12mSJC-MDW
$1,088
4/19Fri
multi-stopDelta
8h 34mMDW-SJC
4/21Sun
multi-stopDelta
9h 12mSJC-MDW
$1,093
4/19Fri
multi-stopDelta
10h 31mMDW-SJC
4/21Sun
multi-stopDelta
11h 25mSJC-MDW
$1,358
4/18Thu
multi-stopDelta
9h 20mMDW-SJC
4/23Tue
multi-stopDelta
9h 20mSJC-MDW
$1,511
4/18Thu
multi-stopDelta
9h 20mMDW-SJC
4/21Sun
multi-stopDelta
8h 24mSJC-MDW
$1,805

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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

Cabin classes: