MDW - SJC

$95 Find Cheap Flights from Chicago Midway Airport to San Jose

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to San Jose departing on 9/29. 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

KAYAK searches hundreds of travel sites at once for deals on flights to San Jose

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Jose, 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 Chicago to San Jose, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Expert advice
Useful Info
Flights Deals

Cheap Flights from Midway to San Jose (MDW-SJC)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to San Jose 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 Midway to San Jose

Sat, Aug 16 - Sat, Aug 23
Delta Logo
4:25 pm - 10:18 pmMDW-SJC
7h 53m1 stop
Delta Logo
10:25 pm - 8:35 amSJC-MDW
8h 10m1 stop
$257Delta
Find Deal
Sat, Aug 16 - Sat, Aug 23
Delta Logo
1:08 pm - 10:39 pmMDW-SJC
11h 31m2 stops
Delta Logo
10:25 pm - 8:35 amSJC-MDW
8h 10m1 stop
$262Delta
Find Deal
Thu, Sep 18 - Sun, Sep 21
Frontier Logo
1:53 pm - 5:55 pmMDW-SJC
30h 02m2 stops
Frontier Logo
2:09 pm - 3:53 pmSJC-MDW
23h 44m1 stop
$264Frontier
Find Deal
Sat, Aug 23 - Mon, Aug 25
Delta Logo
1:43 pm - 8:37 pmMDW-SJC
8h 54m1 stop
Delta Logo
6:25 am - 5:37 pmSJC-MDW
9h 12m1 stop
$266Delta
Find Deal
Fri, Sep 5 - Sun, Sep 7
Frontier Logo
7:15 am - 5:55 pmMDW-SJC
12h 40m2 stops
Frontier Logo
2:09 pm - 3:53 pmSJC-MDW
23h 44m1 stop
$276Frontier
Find Deal
Tue, Oct 21 - Tue, Oct 28
Southwest Logo
5:25 pm - 7:55 pmMDW-SJC
4h 30mnonstop
Southwest Logo
7:30 am - 1:35 pmSJC-MDW
4h 05mnonstop
$297Southwest
Find Deal
Thu, Sep 18 - Sun, Sep 21
Frontier Logo
1:53 pm - 5:55 pmMDW-SJC
30h 02m2 stops
Frontier Logo
2:09 pm - 8:52 pmSJC-MDW
28h 43m2 stops
$298Frontier
Find Deal
Thu, Aug 14 - Wed, Aug 20
Southwest Logo
7:55 pm - 10:25 pmMDW-SJC
4h 30mnonstop
Southwest Logo
6:35 am - 12:45 pmSJC-MDW
4h 10mnonstop
$305Southwest
Find Deal
Thu, Aug 14 - Wed, Aug 20
Southwest Logo
7:55 pm - 10:25 pmMDW-SJC
4h 30mnonstop
Southwest Logo
7:00 am - 4:30 pmSJC-MDW
7h 30m1 stop
$307Southwest
Find Deal
Tue, Sep 16 - Thu, Sep 18
Southwest Logo
5:40 pm - 8:10 pmMDW-SJC
4h 30mnonstop
Southwest Logo
10:00 am - 7:45 pmSJC-MDW
7h 45m2 stops
$308Southwest
Find Deal
Expert advice

Expert advice for your flight from Midway to San Jose

 
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
MDW

Midway offers a compact terminal with three concourses, making navigation easy. Enjoy local dining options like Billy Goat Tavern before your flight.

Read more about MDWby Stefanie Waldek
SJC

For a cost-efficient transfer to San Francisco, take a rideshare to Santa Clara Caltrain station, offering timely service to downtown SF.

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
Useful Info

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

Get data-powered insights and trends into flights from Midway to San Jose 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 Chicago Midway Airport to San Jose?

The average price of all round-trip flights from Chicago Midway Airport to San Jose clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago Midway Airport to San Jose, look for departures on Wednesdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from San Jose, Tuesday is the cheapest day to fly and Sunday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to San Jose, 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 Chicago Midway Airport to San Jose is November, where tickets cost $357 (return) on average. On the other hand, the most expensive months are September and March, where the average cost of round-trip tickets is $516 and $467 respectively.

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

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 $448, prices are generally cheapest when you fly direct.

Good to know

Low seasonJanuary
High seasonMay
Cheapest flight$95
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Chicago Midway Airport to San Jose

When to book flights from Midway to San Jose

Are your dates flexible? Find out the best times to travel from Midway to San Jose 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 Chicago Midway Airport to San Jose flights

  • What is the cheapest flight from Chicago Midway Airport to San Jose?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to San Jose was $95 for a one-way ticket and $257 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and San Jose?

    No

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to San Jose?

    Alaska Airlines, Hawaiian Airlines, American Airlines, and Delta offer inflight Wi-Fi service on the Chicago Midway Airport to San Jose flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to San Jose?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to San Jose flight route.

  • On which days can I fly direct from Chicago Midway Airport to San Jose?

    There are nonstop flights from Chicago Midway Airport to San Jose on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Chicago to San Jose are Southwest and Frontier. With an average price for the route of $459 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $258 and an overall rating of 5.9.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to San Jose?

    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 Chicago Midway Airport to San Jose.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to San Jose?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Jose from Chicago Midway Airport 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 Chicago Midway Airport to San Jose?

    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 San Jose with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SJC 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 Chicago Midway Airport to San Jose?

    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 San Jose from Chicago Midway Airport 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 Chicago Midway Airport to San Jose

  • Looking for a cheap flight? 25% of our users found flights on this route for $564 or less one-way and $396 or less round-trip.

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

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to San Jose.
Find which airlines fly direct from Chicago Midway Airport to San Jose Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

Reviews of the top airlines flying from Midway to San Jose

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Jose. 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 Midway to San Jose? 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 4266 reviews
7.6Entertainment
8.6Crew
7.0Food
8.0Comfort
8.2Boarding
Airline reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

4.0 OkayAnonymous, Jun 2025MDW - LGA
Read more Southwest reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It was a perfect flight in all aspects! Both legs!

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

We’ve all seen the YouTube vids of out of control passengers. But this was an instance of a highly aggressive, bully flight attendant. Yelling in the face of a vet with PTSD who was texting their family. And no , we had not yet been instructed to put our phones in airplane mode. My suggestion is that you should pay whatever difference there is in order to avoid Frontier airlines. Additionally, after 3hrs trying to get customer service frontier offered a $25 voucher. I declined. This experience was so traumatic. To be verbally assaulted and abused by a flight attendant that has the power to say “boo” and I miss my flight ( which was to a family member’s funeral ). Frontier is unsafe and I cannot impress enough how much I discourage anyone ( esp those with any kind of disability like PTSD ) flying on Frontier.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

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

Very bad! No good service delayed my second connection flight

They canceled flight. Hard to believe there was even a plane incoming for us to get on

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Horrendous. I do not recommend Frontier. The passengers lack manners and decency, and the flight attendants lack professionalism. If I wasn’t in a bind to fly with 48 hours notice for a job interview, I would not have selected a flight with Frontier and I never plan to fly with them in the future.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

Everything went as planned. Crew was great. Seats were still not that comfortable.

No frills for sure. No gate announcements about flight delay, not even water to drink on the flight.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.