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SJC - MDW

Find cheap flights from San Jose to Chicago Midway Airport from $141

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 5/4. 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 5/23
Thu 5/30

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 44,632,927 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.

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

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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:00 am - 5:06 pmSJC-MDW
9h 06m2 stops
2:24 pm - 8:37 pmMDW-SJC
8h 13m1 stop
$303Delta
Find Deal
Tue, Jun 4 - Wed, Jun 19
10:20 pm - 1:35 pmSJC-MDW
13h 15m2 stops
2:24 pm - 8:37 pmMDW-SJC
8h 13m1 stop
$323Delta
Find Deal
Mon, Jun 3 - Tue, Jun 11
10:20 pm - 1:35 pmSJC-MDW
13h 15m2 stops
2:24 pm - 11:49 pmMDW-SJC
11h 25m2 stops
$328Delta
Find Deal
Mon, Jun 3 - Tue, Jun 11
12:05 pm - 9:44 pmSJC-MDW
7h 39m1 stop
3:45 pm - 9:43 pmMDW-SJC
7h 58m1 stop
$330Delta
Find Deal
Thu, Oct 17 - Tue, Oct 29
6:00 am - 6:36 pmSJC-MDW
10h 36m2 stops
2:25 pm - 8:37 pmMDW-SJC
8h 12m1 stop
$335Delta
Find Deal
Wed, Jun 26 - Tue, Jul 16
12:21 pm - 5:50 amSJC-MDW
15h 29m2 stops
5:05 am - 4:05 pmMDW-SJC
13h 00m2 stops
Sat, May 25 - Sat, Jun 1
4:40 pm - 5:50 amSJC-MDW
11h 10m1 stop
5:05 am - 4:05 pmMDW-SJC
13h 00m2 stops
Sat, May 25 - Sat, Jun 1
3:10 pm - 12:40 amSJC-MDW
7h 30m1 stop
5:35 am - 2:15 pmMDW-SJC
10h 40m1 stop
$360Southwest
Find Deal
Tue, May 21 - Wed, May 22
8:30 am - 11:25 pmSJC-MDW
12h 55m2 stops
5:35 am - 2:15 pmMDW-SJC
10h 40m1 stop
$365Southwest
Find Deal
Tue, May 21 - Wed, May 22
1:24 pm - 9:47 amSJC-MDW
18h 23m1 stop
8:45 pm - 9:02 amMDW-SJC
14h 17m1 stop
$844Volaris
Find Deal
Wed, Jun 12 - Sun, Jun 16

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 Wednesday being the most expensive.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Delta ($149) and Southwest ($172). The cheapest round-trip tickets were found on Delta ($303) and Southwest ($360).

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

Each day, there are between 1 and 2 nonstop flights that take off from San Jose and land in Chicago Midway Airport, with an average flight time of 4h 07m. The most common departure time is 6:00 am and most flights take off in the morning. 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 Saturday.

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 4h 05m. 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 6:45 am and will be landing in Chicago Midway Airport at 12:55 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

$141
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 $141 for a one-way ticket and $303 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

 
See real verified KAYAK customer reviews for airlines flying from San Jose to Chicago. 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 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 verified KAYAK customer reviews.
8.0
DeltaOverall score based on 11042 reviews
7.9comfort
7.5food
8.6crew
8.0entertainment
8.2boarding
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.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

I didn’t not like that I could not select my seat and ended up with the worse seat.

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

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

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.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Terrible. Seats are bad and the baggage policy is inconsistent

Better than I expected but I did pay for a seat and carry on bags ahead of time.

I hope to avoid flying with them in the future. First flight got cancelled then got stuck with a 13 hour layover in Denver. The process was long and frustrating to many people.

Flight was delayed on the runway for 40 minutes the crew did not even offer even water to passengers to compensate for the flight delayed. The flight was delayed due to aircraft mechanical issues. Worst customer service ever

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.

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.
5/4Sat
2 stops
11h 39mSJC-MDW
$141
7/23Tue
1 stopDelta
9h 29mSJC-MDW
$149
5/4Sat
3 stops
14h 20mSJC-MDW
$154
5/13Mon
1 stopDelta
7h 35mSJC-MDW
$169
6/6Thu
nonstopSouthwest
4h 05mSJC-MDW
$172
5/13Mon
2 stopsDelta
10h 52mSJC-MDW
$174
6/2Sun
1 stopDelta
7h 35mSJC-MDW
$181
6/6Thu
1 stopSouthwest
6h 50mSJC-MDW
$190
7/29Mon
1 stopVolaris
14h 20mSJC-MDW
$428
10/10Thu
1 stopVolaris
18h 13mSJC-MDW
$515

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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.
4/24Wed
multi-stopVolaris
18h 23mSJC-MDW
4/29Mon
multi-stopVolaris
14h 17mMDW-SJC
$868
4/26Fri
multi-stopDelta
7h 50mSJC-MDW
5/3Fri
multi-stopDelta
8h 56mMDW-SJC
$879
4/26Fri
multi-stopDelta
7h 50mSJC-MDW
5/3Fri
multi-stopDelta
8h 34mMDW-SJC
$884
4/26Fri
multi-stopDelta
9h 12mSJC-MDW
4/28Sun
multi-stopDelta
8h 57mMDW-SJC
$908
4/24Wed
multi-stopDelta
8h 50mSJC-MDW
4/29Mon
multi-stopDelta
8h 34mMDW-SJC
$913
4/25Thu
multi-stopVolaris
17h 23mSJC-MDW
4/27Sat
multi-stopVolaris
14h 17mMDW-SJC
$1,026
4/26Fri
multi-stopDelta
8h 35mSJC-MDW
4/28Sun
multi-stopDelta
8h 57mMDW-SJC
$1,078
4/25Thu
multi-stopDelta
7h 50mSJC-MDW
4/27Sat
multi-stopDelta
9h 20mMDW-SJC
$1,083
4/25Thu
multi-stopDelta
10h 17mSJC-MDW
4/27Sat
multi-stopDelta
9h 20mMDW-SJC
$1,088
4/26Fri
multi-stopDelta
10h 17mSJC-MDW
5/3Fri
multi-stopDelta
11h 45mMDW-SJC
$1,109

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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