SJC - MDW

$65 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.
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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
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Cheap Flight Deals from San Jose to Chicago Midway Airport (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 Chicago Midway Airport 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.

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
4:03 pm - 12:17 amSJC-MDW
6h 14m1 stop
6:40 am - 3:03 pmMDW-SJC
10h 23m1 stop
$130Frontier
Find Deal
Wed, Feb 26 - Mon, Mar 3
1:11 pm - 12:17 amSJC-MDW
9h 06m1 stop
7:15 am - 12:11 pmMDW-SJC
6h 56m1 stop
$132Frontier
Find Deal
Thu, Feb 6 - Mon, Feb 10
4:03 pm - 12:21 amSJC-MDW
6h 18m1 stop
8:50 pm - 7:22 pmMDW-SJC
24h 32m1 stop
$140Frontier
Find Deal
Wed, Apr 2 - Thu, Apr 3
4:03 pm - 12:17 amSJC-MDW
6h 14m1 stop
7:05 am - 3:03 pmMDW-SJC
9h 58m1 stop
$150Frontier
Find Deal
Mon, Feb 24 - Wed, Feb 26
6:30 am - 2:22 pmSJC-MDW
5h 52m1 stop
1:16 pm - 8:53 pmMDW-SJC
9h 37m1 stop
$343Delta
Find Deal
Tue, Apr 15 - Tue, Apr 22
6:30 am - 2:22 pmSJC-MDW
5h 52m1 stop
3:02 pm - 11:50 pmMDW-SJC
10h 48m2 stops
$348Delta
Find Deal
Tue, Apr 15 - Tue, Apr 22
9:03 am - 5:31 amSJC-MDW
18h 28m2 stops
7:05 am - 10:41 pmMDW-SJC
17h 36m2 stops
Thu, Feb 13 - Wed, Feb 19
9:03 am - 5:31 amSJC-MDW
18h 28m2 stops
1:26 pm - 9:10 pmMDW-SJC
9h 44m1 stop
Thu, Feb 13 - Wed, Feb 19
11:50 am - 5:55 pmSJC-MDW
4h 05mnonstop
8:35 am - 11:25 amMDW-SJC
4h 50mnonstop
$433Southwest
Find Deal
Thu, Feb 13 - Wed, Feb 19
11:50 am - 5:55 pmSJC-MDW
4h 05mnonstop
4:15 pm - 9:10 pmMDW-SJC
6h 55m1 stop
$438Southwest
Find Deal
Thu, Feb 13 - Wed, Feb 19

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 round-trip flights from San Jose to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Sunday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from San Jose to Chicago Midway Airport. For your return ticket, we recommend flying on a Monday and avoiding Sundays for the best deals.

What is the cheapest month to fly from San Jose to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Jose to Chicago Midway Airport, 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 San Jose to Chicago Midway Airport is March, where tickets cost $236 (return) on average. On the other hand, the most expensive months are June and April, where the average cost of round-trip tickets is $667 and $612 respectively.

Good to know

Low season

June

High season

November

Cheapest flight

$65
Best time to beat the crowds but there is an average 45% increase in price.
Most popular time to fly and prices are also 16% 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 $65 for a one-way ticket and $130 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?

    Alaska Airlines, JetBlue, 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 $518 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 $617 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 $213 or less one-way and $434 or less round-trip.

Prefer to fly direct 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.

Direct 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

Direct 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 4659 reviews
7.7Entertainment
7.2Food
8.7Crew
8.1Comfort
8.2Boarding
Airline reviews

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

10.0 ExcellentRachel, Jan 2025TPA - MDW
Read more Southwest reviews

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

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.

It was terrible, if they ran flights on time it would make a big difference.

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

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!

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

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.

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

It was a redeye flight, so every passenger just wanted to sleep, but through the entire flight, the flight crew made announcements over the loudspeaker at maximum volume every few minutes making sleep impossible. For example: it’s 2am, and the crew decides to give an extremely detailed announcement about snacks and beverages for sale. And 3am is the perfect time to wake up everyone with a lengthy announcement about how to get a coffee refill and how to take advantage of new offer from frontier for a credit card.

The takeoff was the smoothest I've ever experienced on any airline and this is the first time I've flown on frontier so this was an extremely pleasant surprise!

A lady asked to stop the flight after the tunnel pulled away and we began to depart a flight that was already hours late. The attendance respectfully stopped the the plane and had the tunnel return. After the tunnel returned the passenger claimed to have changed her mind . The tunnel was then put in reverse and the passenger remained on the plane .. They should have sent the sick passenger off the plane like initially replaced. They existed a couple off the plane prior to that situation.. So.. all and all.. it was a long and flight.. .

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

With frontier you get what you pay for. The flight was two hours late. It’s a tight fit for the number of people they bring but you get to where you’re going cheap. Sometimes that’s more important than a nifty drink and cool TV..

Charges unexpected. For seat that didnt recline. Please reverse extra seat and carryon charge. Bad business that is a bait and switch.

We had an awful experience getting our bags checked in. Frontier’s check in on the app manipulated us into buying the business package because that was the only option available for a checked bag which included two checked bags per person which we did not need. Upon arriving to the airport, we stood in line for what seemed like forever at the baggage check in and there was no one available at the counter. We were first in line and we were afraid we were going to miss our flight due to the baggage attendant being late. After realizing there were a lot of other people waiting at the baggage check in and no one available. I reached out to Frontier and could not get any customer service so I had to call the airport to page the baggage attendant to send someone to the counter to check in our bags before we were able to go through security , I finally spoke to the attendant at the counter and explained to her that we had to pay for two checked bags person a total of six bags when we only had a total of three bags between three people she said to reach out to Frontier and they would issue a refund for the three bags that we paid for and did not need. I reached out to Frontier which I was not able to reach anybody by phone so I had to go through their automated chat feature, which sent me around in circles until I finally reached a representative to assist me. I explained to them what happened and they explained that they were not able to assist me. I continued to push the issue with them as this was very frustrating and they finally put in a customer service ticket where we were issued a flight credit and we were so disappointed because after this experience, we NEVER want to fly Frontier again, and we do not want a credit that we will not use. Frontier charged us almost $500 for us to check three bags which is absolutely absurd! The customer service agents were not able to offer anything else other than a flight credit and I do not feel like my frustrations were truly heard , we will never use Frontier Airlines again ! Truly Theft by Manipulation! They should be ashamed!

I couldn’t check in because the app didn’t work. It took 3 Frontier employees at the counter to get me checked in. Flight left 3 hours after departure time

While booking it was not obvious that I had to pay for carryon. Realized it only during check-in. Overall, meh!

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