SJC - MDW

$103 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 2/26. 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
1 adult, Economy, 0 bags

KAYAK searches 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$334
Overall average: $419
Delta
Mon 2/23Fri 3/6
SJC - MDW • 2 stops
Cheapest non-stop
$387
Typical prices: $442-$897
Southwest
Fri 2/20Sun 2/22
SJC - MDW • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
SJC's manageable layout ensures quick security lines.
The CTA Orange Line offers a direct route to downtown.
Expert advice
Expert advice
Expert advice
Expert advice
When to travel
February
Cheapest • 21% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San Jose to Midway

Mon, Feb 23 - Fri, Mar 6
Delta Logo
6:25 pm - 8:54 am
SJC
-
MDW
12h 29m
2 stops
Delta Logo
1:29 pm - 10:05 pm
MDW
-
SJC
10h 36m
2 stops
$334Delta
Sat, Feb 21 - Fri, Mar 6
Delta Logo
6:20 am - 4:14 pm
SJC
-
MDW
7h 54m
1 stop
Delta Logo
1:29 pm - 10:05 pm
MDW
-
SJC
10h 36m
2 stops
$370Delta
Thu, Feb 12 - Thu, Feb 19
Delta Logo
9:15 am - 10:31 pm
SJC
-
MDW
11h 16m
2 stops
Delta Logo
1:26 pm - 10:05 pm
MDW
-
SJC
10h 39m
2 stops
$376Delta
Fri, Mar 13 - Mon, Mar 16
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
Southwest Logo
8:00 pm - 10:40 pm
MDW
-
SJC
4h 40mnonstop
$387Southwest
Wed, Mar 4 - Wed, Mar 18
Delta Logo
10:35 pm - 9:54 am
SJC
-
MDW
9h 19m
1 stop
Delta Logo
2:05 pm - 10:58 am
MDW
-
SJC
22h 53m
2 stops
$390Delta
Thu, Feb 5 - Thu, Feb 12
Southwest Logo
6:30 am - 12:40 pm
SJC
-
MDW
4h 10mnonstop
Southwest Logo
8:00 am - 10:50 am
MDW
-
SJC
4h 50mnonstop
$391Southwest
Fri, Feb 20 - Mon, Mar 2
Southwest Logo
12:25 pm - 6:30 pm
SJC
-
MDW
4h 05mnonstop
Southwest Logo
5:00 pm - 9:15 pm
MDW
-
SJC
6h 15m
1 stop
$393Southwest
Thu, Feb 12 - Mon, Feb 16
Southwest Logo
12:25 pm - 6:30 pm
SJC
-
MDW
4h 05mnonstop
Southwest Logo
8:00 am - 10:50 am
MDW
-
SJC
4h 50mnonstop
$395Southwest
Wed, Mar 25 - Sun, Mar 29
Delta Logo
6:15 pm - 8:53 am
SJC
-
MDW
12h 38m
2 stops
Delta Logo
2:05 pm - 11:58 pm
MDW
-
SJC
11h 53m
2 stops
$396Delta
Fri, Feb 13 - Tue, Feb 17
Southwest Logo
3:40 pm - 11:10 pm
SJC
-
MDW
5h 30m
1 stop
Southwest Logo
8:05 am - 10:55 am
MDW
-
SJC
4h 50mnonstop
$397Southwest
Booking Insights

KAYAK's insights & trends for San Jose to Midway flights

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 Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from San Jose to Chicago Midway Airport. For your return ticket, we recommend flying on a Thursday 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 February, where tickets cost $419 (return) on average. On the other hand, the most expensive months are November and January, where the average cost of round-trip tickets is $840 and $597 respectively.

Can I save money by flying with a layover from San Jose to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $417, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from San Jose to Midway

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
SJC

SJC offers a manageable layout with quick security lines, making it ideal for business travelers with early flights.

MDW

The CTA Orange Line provides a direct route from MDW to downtown Chicago in about 25-30 minutes, avoiding traffic issues.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Bill Fink

Bill Fink

Expert on SJC

Bill Fink

Bill Fink

Bill is an award-winning travel writer with extensive credits covering airlines and the aviation industry for publications including AARP, AFAR, The Points Guy and Yahoo. Based in Portland, Oregon, Bill has traveled to more than 75 countries - and been late for his flight in most of them. He once achieved top-level frequent flier status for all of American, Delta and United Airlines during a single year.

Read more

Good to know

Low seasonJanuary
Cheapest flight$103
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 11% 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 $103 for a one-way ticket and $334 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?

    Hawaiian Airlines, American Airlines, Delta, Alaska Airlines, and JetBlue 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?

    You can catch a nonstop flight from San Jose to Chicago Midway Airport on Monday, Tuesday, Thursday, Friday, Saturday, and Sunday.

  • 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.

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 $205 or less one-way and $387 or less round-trip.

Prefer to fly direct from San Jose to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from San Jose to Chicago Midway.
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

Reviews of the top airline flying 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
SouthwestOverall score based on 4256 reviews
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

We got exit row seats both flights. Everything was running on time

10.0 ExcellentMaggie, Jan 2026
FAT - LAS
Read more Southwest reviews

We got exit row seats both flights. Everything was running on time

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

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

Information on your arrival and departure airports