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SJC - MDW

$88 Find cheap flights from San Jose to Chicago Midway Airport

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 9/11. 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
Sat 7/13
Sat 7/20

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 44,216,777 times on KAYAK, and here is why:

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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
10:20 pm - 6:33 amSJC-MDW
6h 13m1 stop
11:32 am - 6:06 pmMDW-SJC
8h 34m1 stop
$180Frontier
Find Deal
Fri, Aug 16 - Fri, Aug 23
10:20 pm - 6:33 amSJC-MDW
6h 13m1 stop
10:00 pm - 4:51 pmMDW-SJC
20h 51m1 stop
$182Frontier
Find Deal
Thu, Aug 15 - Mon, Aug 19
10:20 pm - 6:33 amSJC-MDW
6h 13m1 stop
10:00 pm - 4:51 pmMDW-SJC
20h 51m1 stop
$183Frontier
Find Deal
Thu, Aug 15 - Wed, Aug 21
11:30 am - 11:52 amSJC-MDW
22h 22m1 stop
11:32 am - 6:06 pmMDW-SJC
8h 34m1 stop
$184Frontier
Find Deal
Mon, Aug 12 - Fri, Aug 16
6:15 am - 6:05 pmSJC-MDW
9h 50m1 stop
2:24 pm - 8:39 pmMDW-SJC
8h 15m1 stop
$236Delta
Find Deal
Tue, Aug 20 - Wed, Aug 21
7:25 am - 9:38 pmSJC-MDW
12h 13m2 stops
2:07 pm - 8:30 pmMDW-SJC
8h 23m1 stop
$241Delta
Find Deal
Sat, Sep 21 - Wed, Sep 25
6:50 pm - 12:55 amSJC-MDW
4h 05mnonstop
7:30 am - 6:10 pmMDW-SJC
12h 40m1 stop
$453Southwest
Find Deal
Mon, Jun 24 - Thu, Jun 27
5:00 pm - 12:55 amSJC-MDW
5h 55m1 stop
11:35 am - 9:35 pmMDW-SJC
12h 00m1 stop
$458Southwest
Find Deal
Mon, Jun 24 - Thu, Jun 27
7:50 am - 4:51 amSJC-MDW
19h 01m1 stop
8:58 pm - 10:48 amMDW-SJC
15h 50m1 stop
Sun, Jun 30 - Wed, Jul 3
6:42 am - 8:17 pmSJC-MDW
35h 35m3 stops
8:00 am - 11:46 pmMDW-SJC
17h 46m3 stops
Thu, Jul 11 - Sat, Jul 13

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, Saturday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago Midway Airport back to San Jose, the best deals are generally found on Monday, with Saturday 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 Frontier ($88) and Delta ($118). The cheapest round-trip tickets were found on Frontier ($180) and Delta ($236).

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

Each day, there are between 1 and 6 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 22 flights. The most frequent day of departure is Friday, when 27% 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 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 6:30 am and will be landing in Chicago Midway Airport at 12:40 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 6:50 pm and lands at 12:55 am.

Good to know

Low season

December

High season

May

Cheapest flight

$88
Best time to beat the crowds with an average 65% drop in price.
Most popular time to fly with an average 10% increase in price.
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 $88 for a one-way ticket and $180 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.

  • Which is the best airline for flights from San Jose to Chicago, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from San Jose to Chicago are Delta and Frontier. With an average price for the route of $587 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $207 and an overall rating of 6.2.

  • 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

KAYAK’s top tips for finding a cheap flight from San Jose to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $405 or less round-trip.

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 10000 reviews
7.9Comfort
8.2Boarding
7.4Food
8.0Entertainment
8.6Crew
Airline reviews

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

4.0 OkayBrooke, Jun 2024SFO - MSP
Read more about Delta reviews

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

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

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

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

I did not enjoy the trip home on Frontier for several reasons: there is too much cost besides the flight, which was more than I would normally pay, then having to pay for luggage, and carry-on, seat (if you want to reserve when booking) then you must pay over $3 for a can of soda, and $4 for a snack. A cup of water is free.

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

I appreciated the upgrade to free cary-on bag and seat selection at no charge

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

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

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.
9/11Wed
1 stopFrontier
6h 13mSJC-MDW
$88
8/26Mon
1 stopFrontier
6h 13mSJC-MDW
$90
8/22Thu
1 stopFrontier
21h 01mSJC-MDW
$93
9/12Thu
1 stopFrontier
6h 13mSJC-MDW
$98
8/31Sat
1 stopFrontier
22h 21mSJC-MDW
$101
10/22Tue
1 stopDelta
9h 29mSJC-MDW
$118
9/11Wed
2 stopsDelta
10h 25mSJC-MDW
$154
6/18Tue
1 stop
20h 13mSJC-MDW
$240
8/22Thu
3 stops
25h 48mSJC-MDW
$253
6/28Fri
1 stopVolaris
14h 20mSJC-MDW
$537

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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.
6/18Tue
multi-stopSouthwest
11h 20mSJC-MDW
6/20Thu
nonstopSouthwest
4h 30mMDW-SJC
$677
6/18Tue
multi-stopSouthwest
11h 20mSJC-MDW
6/20Thu
multi-stopSouthwest
6h 45mMDW-SJC
$686
6/18Tue
multi-stopSouthwest
11h 20mSJC-MDW
6/20Thu
multi-stopSouthwest
13h 25mMDW-SJC
$691
6/18Tue
nonstopSouthwest
4h 10mSJC-MDW
6/20Thu
nonstopSouthwest
4h 30mMDW-SJC
$712
6/18Tue
multi-stopDelta
9h 04mSJC-MDW
6/20Thu
multi-stopDelta
8h 35mMDW-SJC
$772
6/15Sat
multi-stopDelta
7h 20mSJC-MDW
6/28Fri
multi-stopDelta
8h 13mMDW-SJC
$895
6/15Sat
multi-stopDelta
13h 48mSJC-MDW
6/28Fri
multi-stopDelta
8h 13mMDW-SJC
$900
6/15Sat
multi-stopDelta
7h 20mSJC-MDW
6/18Tue
multi-stopDelta
8h 57mMDW-SJC
$945
6/15Sat
multi-stopDelta
7h 20mSJC-MDW
6/18Tue
multi-stopDelta
10h 46mMDW-SJC
$950
6/15Sat
multi-stopDelta
8h 49mSJC-MDW
6/28Fri
multi-stopDelta
12h 25mMDW-SJC
$968

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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:

$405