SJC - MDW

$100 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 1/8. 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
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$314
Overall average: $532
Delta
Tue 1/20Tue 1/27
SJC - MDW • 2 stops
Cheapest non-stop
$387
Typical prices: $532-$547
Southwest
Fri 1/16Mon 1/19
SJC - MDW • Non-stop
Our travelers' advice
AI-generated summary based on content written by travel experts
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 • 13% price drop
May
Most popular
Good to know
Good to know
+1
+1
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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

Tue, Jan 20 - Tue, Jan 27
Delta Logo
6:25 pm - 8:52 amSJC-MDW
12h 27m2 stops
Delta Logo
9:50 am - 5:40 pmMDW-SJC
9h 50m2 stops
$314Delta
Find Deal
Fri, Jan 16 - Tue, Jan 20
Delta Logo
9:15 am - 8:52 amSJC-MDW
21h 37m2 stops
Delta Logo
1:49 pm - 10:57 amMDW-SJC
23h 08m2 stops
$337Delta
Find Deal
Sat, Dec 13 - Wed, Dec 17
Delta Logo
7:45 pm - 9:19 amSJC-MDW
11h 34m2 stops
Delta Logo
1:50 pm - 8:36 pmMDW-SJC
8h 46m1 stop
$350Delta
Find Deal
Tue, Jan 13 - Sun, Jan 18
Delta Logo
7:45 am - 10:07 pmSJC-MDW
12h 22m2 stops
Delta Logo
1:49 pm - 10:57 amMDW-SJC
23h 08m2 stops
$354Delta
Find Deal
Sat, Dec 13 - Tue, Dec 16
Delta Logo
7:45 pm - 9:19 amSJC-MDW
11h 34m2 stops
Delta Logo
1:50 pm - 11:53 pmMDW-SJC
12h 03m2 stops
$355Delta
Find Deal
Tue, Jan 13 - Mon, Jan 19
Delta Logo
7:45 am - 10:07 pmSJC-MDW
12h 22m2 stops
Delta Logo
12:48 pm - 9:20 pmMDW-SJC
10h 32m1 stop
$360Delta
Find Deal
Thu, Jan 8 - Thu, Jan 15
Delta Logo
6:25 pm - 8:52 amSJC-MDW
12h 27m2 stops
Delta Logo
9:50 am - 7:12 pmMDW-SJC
11h 22m2 stops
$365Delta
Find Deal
Fri, Jan 16 - Tue, Jan 20
Delta Logo
9:15 am - 8:52 amSJC-MDW
21h 37m2 stops
Delta Logo
6:00 am - 12:56 pmMDW-SJC
8h 56m1 stop
$373Delta
Find Deal
Sat, Jan 17 - Sun, Jan 18
Delta Logo
5:54 am - 8:52 amSJC-MDW
24h 58m2 stops
Delta Logo
1:49 pm - 10:57 amMDW-SJC
23h 08m2 stops
$377Delta
Find Deal
Sat, Jan 17 - Sun, Jan 18
Delta Logo
9:15 am - 8:52 amSJC-MDW
21h 37m2 stops
Delta Logo
1:49 pm - 9:28 pmMDW-SJC
9h 39m1 stop
$383Delta
Find Deal
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 Friday 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 $413 (return) on average. On the other hand, the most expensive months are September and August, where the average cost of round-trip tickets is $587 and $557 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $551 on average.

Expert advice

Expert advice for your flight from San Jose to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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$100
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly and prices are also 2% 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 $100 for a one-way ticket and $314 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, Delta, American Airlines, and Hawaiian Airlines 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.

  • Which airline alliances offer flights from San Jose to Chicago Midway Airport?

    Star Alliance is the only airline alliance operating flights between San Jose and Chicago Midway Airport.

  • 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from San Jose to Chicago are Southwest and United Airlines. With an average price for the route of $514 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $472 and an overall rating of 7.4.

  • 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 $193 or less one-way and $446 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 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
SouthwestOverall score based on 4252 reviews
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

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

10.0 ExcellentGordon, Nov 2025SAN - OAK
Read more Southwest reviews

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.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

This airline sucks. They offer low rates then charge you for everything, the app does not work well, the seats are the most uncomfortable. Maintenance issues on the flight, and you still have to sit through their credit card commercials. People are nice enough but does not make up for overall poor experience.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

We were delayed three times ,and that destroyed my plans, and reservations

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

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

Information on your arrival and departure airports