SJC - MDW

$63 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 2/12. 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

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 46,646,933 times on KAYAK, and here is why:

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Cheap Flight Deals from San Jose to Chicago Midway Airport (SJC-MDW)

 
These are the cheapest deals for flights from San Jose to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from San Jose to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from San Jose to Midway.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
5:23 pm - 11:48 amSJC-MDW
16h 25m1 stop
7:15 am - 12:08 pmMDW-SJC
6h 53m1 stop
$158Frontier
Find Deal
Thu, Jan 9 - Sun, Jan 12
2:28 pm - 12:13 amSJC-MDW
7h 45m1 stop
7:15 am - 12:08 pmMDW-SJC
6h 53m1 stop
$168Frontier
Find Deal
Fri, Dec 13 - Sun, Dec 15
5:19 pm - 11:48 amSJC-MDW
16h 29m1 stop
10:27 pm - 11:50 amMDW-SJC
15h 23m1 stop
$178Frontier
Find Deal
Sat, Dec 14 - Wed, Dec 18
6:06 pm - 5:33 amSJC-MDW
33h 27m2 stops
10:44 am - 9:35 amMDW-SJC
24h 51m2 stops
Sun, Dec 29 - Sun, Jan 5
6:06 pm - 5:33 amSJC-MDW
33h 27m2 stops
1:24 pm - 7:46 amMDW-SJC
20h 22m2 stops
Sun, Dec 29 - Fri, Jan 3
6:29 am - 4:21 pmSJC-MDW
7h 52m1 stop
6:00 am - 12:10 pmMDW-SJC
8h 10m1 stop
$326Delta
Find Deal
Tue, Jan 14 - Tue, Jan 21
5:55 am - 6:32 pmSJC-MDW
10h 37m2 stops
2:15 pm - 9:07 pmMDW-SJC
8h 52m1 stop
$331Delta
Find Deal
Sat, Dec 14 - Wed, Dec 18
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
9:45 am - 12:35 pmMDW-SJC
4h 50mnonstop
$374Southwest
Find Deal
Mon, Jan 13 - Thu, Jan 16
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
4:15 pm - 9:10 pmMDW-SJC
6h 55m1 stop
$379Southwest
Find Deal
Tue, Jan 14 - Tue, Jan 21
2:58 pm - 8:59 pmSJC-MDW
28h 01m3 stops
8:39 pm - 9:02 amMDW-SJC
14h 23m1 stop
$814Volaris
Find Deal
Sat, Mar 29 - Mon, Mar 31

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, Sunday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago Midway Airport back to San Jose, the best deals are generally found on Monday, with Sunday being the most expensive.

Good to know

Low season

March

High season

November

Cheapest flight

$63
Best time to beat the crowds with an average 54% drop in price.
Most popular time to fly and prices are also 27% 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 $63 for a one-way ticket and $158 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?

    JetBlue, Alaska Airlines, American Airlines, and Delta offer 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 Boeing 737 MAX 8 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, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from San Jose to Chicago are Southwest and Delta. With an average price for the route of $483 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $650 and an overall rating of 8.0.

  • 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 $188 or less one-way and $431 or less round-trip.

Prefer to fly non-stop from San Jose to Chicago Midway Airport?

Find which airlines fly direct from San Jose Airport to Chicago Midway Airport, 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 4 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.
8.1
SouthwestOverall score based on 5005 reviews
7.2Food
7.7Entertainment
8.2Boarding
8.7Crew
8.1Comfort
Airline reviews

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

10.0 ExcellentJohn, Nov 2024OAK - LAS
Read more Southwest reviews

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a hell hole of an airport. It is the new LaGuardia. Everything Cobbled together. Security gates closed. Terri directional signage

I used to fly SWA all the time. I know the crew has their little acts that are often fun, and entertaining. On this flight one of the crew was just not nice. Very surprising.

I like that it was on time and the staff was friendly.

The plane arrived 25 minutes late, and the Wi-Fi was slower than it usually is.

Forget beverage, they didn't even have water for half the passangers?

Can not wait for seating change to reduce the amount of pre boards - it’s disheartening the abuse. And then then deplaning

If your boarding Military, it should be with ore board, and with my spouse, so rude and stupid to not let us board together and before a group. All the other airlines clearly understand Military courtesy, this is why I Rarely fly SWA and Always fly Alaska

I actually received a notification from kayak on email but not one by text from Delta when my departure gait changed and I almost missed my flight

New boarding doesn't make sense. Filling front first is slow.

Delta flight was great from the check in all the way to arrival. However, I had a very bad experience. I requested a wheelchair and the wheelchair employee that went to pick me up from the plane in Boston to bring me to the baggage claims told me I have to pay him. I was under the impression that it was a free service and I usually give tips but the person forced me to pay and since I said no because I was upset with his demand when my daughter walked in to pick me up he demanded payment from my daughter who paid him thinking maybe now it is a charged service.

Horrible. Grateful to be alive but spent 13 hours at airport only to return back to my familys house and flight changed to next day. They tried to fix a part on plane, had no back up plane and after 10 hours , reattempted the flight and it STILL wasn't fixed. We got a meal voucher and rescheduled flight but there should be some other compensation for the 15 hours spent in airport

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

My seat was changed at the last minute and I was moved to the last row, right next to the bathroom despite selecting my seat well in advance. I was also made to check my carry on due to space but when I got on the plane there was significant empty overhead space. Picking up my carry on from the luggage carousel added time to my trip which had already been extended due to delay.

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!

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

The staff was very friendly. The seats seemed quite small. Overall the flight was pleasant.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.

Exceptional, I’d like to specifically recognize Robert for his outstanding customer service. He is professional, pleasant, and personable.

Stop changing gates at sfo. When you are elderly going back for it’s not fun.

We understand and comply with Frontier’s bag sizes. We’ve had some problems in past while having to await other passengers who do not understand the baggage restrictions or have not prepaid and that is usually our biggest concern (others delaying us) with flying Frontier. Flying OUT of ONT, however, has always been a great experience. I’ve also noted even on delayed Frontier flights very knowledgeable pilots who manage expectations well.

There was no easy way to check in. I don't want to install an app to checkin. I will use alaska from now on because they have a web check in method that is easy.

Horrible! The short distance flight ended up taking 5 hrs! There was a 3 hr delay for the flight to take off and there was a 70 min wait on the tarmac for some bogus reason that the pilot said the gate he was supposed to board was taken up. After a 30 min wait he said the plane that was supposed to push out of the gate called a medical emergency and 40 min later he ended up boarding another gate. For the initial 3 hr delay there was no information/alert about the gate or delay in the app or the boards up until the boarding time and even beyond! Had to walk all the way to the end of the terminal to find the frontier staff to ask what was going on. Avoid this airline at all costs! If you have carryon bags or checked bags , their prices come equivalent to the prices of more reliable airlines. They are the worst in timeliness at 60% (reported as delayed) this year (check the data) by a high margin even compared to the second worst airline. If you are ok with having a miserable flight experience with the odds close to flip of a coin, feel free to try them. If you value your time , money and flying experience, stay away.

Allowed me to chose my seat without extra charge (I purchased full-price ticket) and boarding was in group1. Didn't even serve water.

I went to the Frontier counter in San Jose at 1030am or so on Sunday 10/13/24 to see if I could get an earlier flight to San Diego in lieu of my reserved 630pm flight. One thing led to another, and I was able to obtain an open seat for about $ 56. on the earlier flight. Fine. Then the agent asked if I "was checking a bag". Not knowing that carry-ons cost extra per Frontier policy, I thought that she meant a regular checked bag. Therefore, I said no. Once I got to the gate, the same gate agent who sold me a ticket told me that I had to pay $99 for a carry-on, and that all bags were extra on Frontier. Having never flown on Frontier, I was not aware of this. Part of the issue was that she was not a native English speaker, so there was a miscommunication as to what "bag" meant. I would have preferred for her to have clearly let me know at the front counter that any bag including a carry-on cost $99. It would have had the same outcome, as I had to take my carry-on. But it got hectic at the last minute at the gate itself. The baggage policy should have mentioned "including carry-ons" when we first spoke.

Most horrible airlines. Please avoid it. It's ok to spend $50 extra for delta, united or Alaska

Every day about it was very different all the boarding pass where all wrong l miss flight no refund all crazy

Staff members pretty horrible when boarding. No care for customers

The trip was good but the last minute changes I didn’t like because I had already talked to the attendee and they didn’t help me with my ticket I was having trouble checking in and when the time was up they help me but charge me for that and last minute luggage it was a small bag. After I was in the airplane I realized you were charging because the flight was almost empty and you have to get the money some how. Thanks for everything.

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.
2/12Wed
1 stopFrontier
6h 14mSJC-MDW
$63
12/9Mon
1 stopFrontier
7h 45mSJC-MDW
$64
12/11Wed
1 stopDelta
7h 37mSJC-MDW
$163
12/25Wed
2 stopsDelta
13h 51mSJC-MDW
$168
1/8Wed
nonstopSouthwest
4h 05mSJC-MDW
$187
1/7Tue
1 stopSouthwest
7h 20mSJC-MDW
$196
12/20Fri
3 stops
35h 55mSJC-MDW
$270
12/21Sat
2 stops
23h 06mSJC-MDW
$271
3/14Fri
3 stopsVolaris
28h 01mSJC-MDW
$398
3/16Sun
3 stopsVolaris
28h 01mSJC-MDW
$408

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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.
11/26Tue
multi-stopFrontier
8h 33mSJC-MDW
12/5Thu
multi-stopFrontier
6h 53mMDW-SJC
$238
11/26Tue
multi-stopFrontier
8h 33mSJC-MDW
11/29Fri
multi-stopFrontier
7h 41mMDW-SJC
$256
11/25Mon
multi-stopFrontier
11h 45mSJC-MDW
11/29Fri
multi-stopFrontier
7h 41mMDW-SJC
$302
11/26Tue
multi-stopFrontier
8h 33mSJC-MDW
11/29Fri
multi-stopFrontier
7h 41mMDW-SJC
$322
11/26Tue
multi-stop
27h 25mSJC-MDW
12/5Thu
multi-stop
15h 07mMDW-SJC
$647
11/26Tue
multi-stop
27h 25mSJC-MDW
12/5Thu
multi-stop
26h 20mMDW-SJC
$658
11/26Tue
nonstopSouthwest
4h 05mSJC-MDW
12/5Thu
multi-stopSouthwest
6h 45mMDW-SJC
$703
11/26Tue
nonstopSouthwest
4h 05mSJC-MDW
12/5Thu
nonstopSouthwest
4h 45mMDW-SJC
$722
11/23Sat
multi-stopDelta
7h 16mSJC-MDW
11/29Fri
multi-stopDelta
11h 57mMDW-SJC
$990
11/23Sat
multi-stopDelta
10h 30mSJC-MDW
11/29Fri
multi-stopDelta
11h 57mMDW-SJC
$995

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Everything you need to know for your flight from San Jose to Midway

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