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SJC - MDW

Find cheap flights from San Jose to Chicago Midway Airport from $80

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Jose to Midway departing on 4/16. 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
jue. 4/18
jue. 4/25

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Chicago, 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 San Jose to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 47,600,107 times on KAYAK, and here is why:

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Cheap flight deals from San Jose to Midway

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Jose to Midway 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.
9:15 am - 11:36 amSJC-MDW
24h 21m1 stop
10:59 pm - 7:15 amMDW-SJC
10h 16m1 stop
mar., abr. 16 - mar., abr. 30
8:53 pm - 11:36 amSJC-MDW
12h 43m1 stop
10:59 pm - 7:15 amMDW-SJC
10h 16m1 stop
lun., abr. 22 - mar., abr. 23
6:30 am - 10:05 pmSJC-MDW
13h 35m2 stops
10:59 pm - 7:15 amMDW-SJC
10h 16m1 stop
mar., abr. 16 - mar., abr. 30
8:53 pm - 11:36 amSJC-MDW
12h 43m1 stop
10:59 pm - 8:16 amMDW-SJC
11h 17m1 stop
lun., abr. 15 - lun., abr. 22
9:42 am - 11:36 amSJC-MDW
23h 54m1 stop
10:12 am - 10:48 pmMDW-SJC
14h 36m2 stops
mié., abr. 17 - mié., abr. 24
9:42 am - 11:36 amSJC-MDW
23h 54m1 stop
10:30 am - 10:48 pmMDW-SJC
14h 18m2 stops
mié., abr. 10 - sáb., abr. 13
4:11 pm - 8:39 pmSJC-MDW
26h 28m2 stops
10:59 pm - 7:15 amMDW-SJC
10h 16m1 stop
vie., abr. 19 - lun., abr. 22
9:19 pm - 11:36 amSJC-MDW
12h 17m1 stop
10:59 pm - 7:15 amMDW-SJC
10h 16m1 stop
jue., may. 2 - lun., may. 6
6:30 am - 5:20 pmSJC-MDW
8h 50m1 stop
3:45 pm - 10:45 pmMDW-SJC
9h 00m1 stop
$236Delta
Find Deal
mié., may. 1 - sáb., may. 11
6:30 am - 5:20 pmSJC-MDW
8h 50m1 stop
1:25 pm - 10:22 pmMDW-SJC
10h 57m2 stops
$241Delta
Find Deal
mar., abr. 30 - mié., may. 1

Flights from San Jose to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from San Jose to Midway 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 San Jose to Chicago Midway Airport?

The average price of all flights from San Jose to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
For San Jose to Chicago Midway Airport, Tuesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago Midway Airport back to San Jose, the best deals are generally found on Monday, with Friday being the most expensive.

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

Each day, there are between 2 and 3 nonstop flights that take off from San Jose and land in Chicago Midway Airport, with an average flight time of 4h 06m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 19 flights. The most frequent day of departure is Monday, when 16% of all weekly flights depart. The fewest flights depart on a Sunday.

How long does a flight from San Jose to Chicago Midway Airport take?

Nonstop flights from San Jose generally make it to Chicago Midway Airport in 6h 43m. The flying distance between the two cities is 1,832 miles.

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

Early birds can take the earliest flight from San Jose at 6:40 am and will be landing in Chicago Midway Airport at 12:50 pm.

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

If you prefer to fly at night, the latest flight from San Jose to Chicago Midway Airport jets off at 12:25 pm and lands at 6:30 pm.

Good to know

Low season

October

High season

May

Cheapest flight

$80
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly and prices are also 19% lower on average.
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
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 San Jose to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from San Jose to Chicago Midway Airport was $80 for a one-way ticket and $154 for a round-trip.

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

    A passport is not required to fly from San Jose to Chicago Midway Airport.

  • Which airlines offer Wi-Fi service onboard planes from San Jose to Chicago Midway Airport?

    Only JetBlue offers inflight Wi-Fi service on the San Jose to Chicago Midway Airport flight route.

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

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the San Jose to Chicago Midway Airport flight route.

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

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

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

    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 San Jose to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from San Jose 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 San Jose to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to San Jose with another airline. Booking your flights between San Jose and MDW 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 San Jose to Chicago Midway Airport?

    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 Chicago Midway Airport from San Jose 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 San Jose to Chicago Midway Airport?

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top 3 airlines serving from San Jose to Midway

Need help choosing which airline to fly with from San Jose to Midway? 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 KAYAK reviews.
8.0
DeltaOverall score based on 11551 reviews
75food
81overall
82boarding
86crew
79comfort
81entertainment
Airline reviews

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

Read more about Delta

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

Plane was late because of a mechanical malfunction and the food listed as available was not. Flight attendants seem over worked and under paid. They just done seem happy. And that can be seen in their faces.

Waited 3 hours on a plane to de-ice due to manpower issues. Waited another hour and a half once we landed because of a gate issue. Missed my connections. Created. A total of 13 hours of delay.

Great, on time departure, friendly and accommodating crew, great leg room, Smith flight

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

Like most domestic flights in the US, you are basically on your own with this airline when it comes to food, so be sure to purchase meals and drinks ahead of time or expect to arrive starving and dehydrated (like I was).

You need to be a hacker to get the (Free) WiFi

I guess they don’t serve drinks on planes anymore

The flight was overbooked and the staff at the gate started calling for volunteers to drop out and offering incentives. That delayed the flight

Do not get fooled by the term “Delta One” flat bed! The seats were super narrow. The ottoman for the feet was so narrow that when you recline the seat in flat bed position, you can only fit one foot in the 8” width space. There was only 1 flight attendant for First Class. The breakfast took 2 hours to get served. Instead of offering French Toast, the served bread pudding. The champagne with orange juice or Mimosa tasted terrible. Almost all the movies offered were ridiculously old. For a long flight from San Francisco to NY, it was frustrating! I DO NOT RECOMMEND this flight!!!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The flights from Ottawa to Albuquerque went smoothly enough though on on flight they didn't have how water for coffee or tea and on another there there was no ice. The return flights from Albuquerque were delayed by mechanical problems on both flights. Ottawa was a ground crew maintenance issue.

The male air hostess was rude and didn’t provide good customer service. Didn’t even offer me a drink

The staff was phenomenal. I can’t think of anything that could be better. Will be flying with UA again

Nothing bad to say about the actual crew or airline. It was nice to have a complimentary FULL can of soda, as well as a snack. Blankets and earbuds were also provided at no cost for this red eye flight. I especially appreciated the free WiFi and movie selection with the Bluetooth option. It helped the flight pass more quickly. No matter who you fly, boarding and disembarking are always SUCH a pain. As I mentioned, this is on the passengers and not the crew!!

Wifi did not work. Cut off on and off every 10 min

The flight was delayed and I had to cancel because I would have missed my connection and there were no other flights for the next two days. They also lost my bag!!

My first time to fly Frontier and loved it! Boarding was super easy as we only had personal items. Crew was helpful and funny and the plane was clean. Pilot was also great at landing the plane smoothly.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

late late late late no accountability no refund no adjustment no reasonable solution

This isna terribly run airlines. If you're one minute late, they will deny your ticket. Don't waste your time or money

Nothing I missed my first flight because my boarding pass said one thing and another passenger on the same flight said another. I didn’t get notified of a gate change until 8:39 pm which was one minute before the flight departed at 8:40pm when we explained this to gate agent Dorsey prior to the flight departing she was extremely short and had nasty attitude. Some of the passengers in my party including myself needed to catch that flight due work the next which included presentations and court litigation. We were deeply saddened and frustrated how Frontier handled this situation. We were told that the flight was over booked by 19 seats and they constantly change gates to make people miss their flight. If that is true I will ensure there will be a class action lawsuit against frontier airlines.

Flight was delayed for more than 3 hours, crew at ONT airport was rude, and when we got to DFW the airplane had an issue landing, we had to be taxied to the terminal, and the luggage was hold until the next day.

Several delays in a row totaling two hours with no information announcements and no explanations given. Rude and unapologetic onboard flight attendant addressing those of us in overpriced emergency exits as if we were idiots. It had been a while since I felt treated like cattle. I will do my best to avoid Frontier as much as possible in the future.

Well the first and worst thing is that you have to pay for a carry on bag. Which they tell you if you don’t read it when you book your flight. You can do it through their website at the ticket area. The staff in Sacramento were RUDE and wouldn’t answer any questions. I will NEVER book with Frontier again. Save the headache and book with Southwest so you don’t have to pay to carry your own bag on the plane. It cost me 41 and 37. On top of my fare. Which by the way went up as soon as I booked it. First it said 38 and then wouldn’t you know it, once I was ready to book, it went up to 78.

Pros: "Frontier delayed the flight 3 hrs with 30 min notice. Cancelled because connection to SLC would have been missed until next morning"
Cons: "Frontier had no customer service at Fresno desk."

Book cheap flights from San Jose to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from San Jose to Chicago found on KAYAK in the last 72 hours.
4/16mar.
1 stop
27h 06mSJC-MDW
$80
4/16mar.
2 stops
13h 14mSJC-MDW
$85
4/23mar.
2 stops
13h 35mSJC-MDW
$90
4/17mié.
2 stops
32h 34mSJC-MDW
$96
4/17mié.
1 stop
26h 36mSJC-MDW
$100
5/11sáb.
1 stopDelta
8h 43mSJC-MDW
$118
4/16mar.
1 stopDelta
8h 50mSJC-MDW
$119
5/13lun.
1 stopDelta
8h 43mSJC-MDW
$181
4/12vie.
1 stopDelta
7h 50mSJC-MDW
$189
4/10mié.
1 stopVolaris
18h 23mSJC-MDW
$337

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Last minute flights from San Jose to Midway

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 San Jose to Chicago that are departing in the next 10 days.
3/24dom.
multi-stop
11h 58mSJC-MDW
4/10mié.
multi-stop
14h 20mMDW-SJC
$374
3/24dom.
multi-stop
11h 58mSJC-MDW
4/4jue.
multi-stop
13h 52mMDW-SJC
$430
3/21jue.
multi-stop
22h 40mSJC-MDW
3/23sáb.
multi-stop
29h 14mMDW-SJC
$734
3/21jue.
multi-stop
26h 22mSJC-MDW
3/24dom.
multi-stop
28h 39mMDW-SJC
$735
3/21jue.
multi-stop
13h 01mSJC-MDW
3/24dom.
multi-stop
17h 25mMDW-SJC
$752
3/21jue.
multi-stop
11h 58mSJC-MDW
3/23sáb.
multi-stop
8h 00mMDW-SJC
$838
3/20mié.
multi-stop
12h 09mSJC-MDW
3/22vie.
multi-stop
17h 27mMDW-SJC
$864
3/21jue.
multi-stopDelta
7h 13mSJC-MDW
3/25lun.
multi-stopDelta
11h 18mMDW-SJC
$908
3/21jue.
multi-stopDelta
7h 41mSJC-MDW
3/25lun.
multi-stopDelta
11h 02mMDW-SJC
$913
3/21jue.
multi-stop
17h 35mSJC-MDW
3/24dom.
multi-stop
29h 47mMDW-SJC
$986

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San Jose - Chicago Midway Airport Flights

Departure:

San Jose (SJC)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - San Jose

Cabin classes:

$373