MDW - SJC

$106 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 5/24. 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

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 22% 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
Useful Info
Flights Deals

Cheap Flights from Midway to San Jose

 
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.

Recent round-trip flight deals from Midway to San Jose

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to San Jose.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
2:44 pm - 11:18 amMDW-SJC
22h 34m1 stop
Frontier Logo
2:30 pm - 2:56 pmSJC-MDW
22h 26m1 stop
$213Frontier
Find Deal
Sat, Jun 7 - Sun, Jun 8
Frontier Logo
2:44 pm - 11:18 amMDW-SJC
22h 34m1 stop
Frontier Logo
2:30 pm - 2:56 pmSJC-MDW
22h 26m1 stop
$218Frontier
Find Deal
Sat, Jun 7 - Sun, Jun 8
Frontier Logo
6:25 am - 1:40 pmMDW-SJC
9h 15m1 stop
Frontier Logo
12:13 pm - 8:53 pmSJC-MDW
6h 40m1 stop
$238Frontier
Find Deal
Mon, Jun 2 - Sun, Jun 8
Delta Logo
1:47 pm - 8:33 pmMDW-SJC
8h 46m1 stop
Delta Logo
10:25 pm - 9:41 amSJC-MDW
9h 16m1 stop
$299Delta
Find Deal
Tue, Jun 10 - Tue, Jun 17
Delta Logo
1:55 pm - 8:31 pmMDW-SJC
8h 36m1 stop
Delta Logo
9:00 am - 9:27 pmSJC-MDW
10h 27m2 stops
$304Delta
Find Deal
Tue, May 27 - Tue, Jun 3
Southwest Logo
8:35 am - 1:25 pmMDW-SJC
6h 50m1 stop
Southwest Logo
6:35 am - 12:45 pmSJC-MDW
4h 10mnonstop
$321Southwest
Find Deal
Wed, Jun 4 - Wed, Jun 11
Southwest Logo
7:30 am - 1:45 pmMDW-SJC
8h 15m2 stops
Southwest Logo
6:35 am - 12:45 pmSJC-MDW
4h 10mnonstop
$326Southwest
Find Deal
Wed, Jun 4 - Wed, Jun 11
Southwest Logo
5:05 pm - 7:40 pmMDW-SJC
4h 35mnonstop
Southwest Logo
9:20 am - 3:30 pmSJC-MDW
4h 10mnonstop
$331Southwest
Find Deal
Wed, Jun 4 - Tue, Jun 10
Delta Logo
4:15 pm - 11:00 pmMDW-SJC
8h 45m1 stop
Delta Logo
10:25 pm - 9:41 amSJC-MDW
9h 16m1 stop
$335Delta
Find Deal
Thu, Jun 5 - Tue, Jun 17
Southwest Logo
7:30 am - 1:45 pmMDW-SJC
8h 15m2 stops
Southwest Logo
3:40 pm - 12:05 amSJC-MDW
6h 25m1 stop
$336Southwest
Find Deal
Wed, Jun 4 - Wed, Jun 11
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.

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 $200 on average.

Good to know

Low seasonJanuary
High seasonFebruary
Cheapest flight$106
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 4% increase in price.
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 $106 for a one-way ticket and $213 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?

    American Airlines, Alaska Airlines, Hawaiian 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 $458 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 $175 or less one-way and $371 or less round-trip.

Prefer to fly direct from Chicago Midway Airport 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
See more direct flights

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 4294 reviews
8.2Boarding
7.1Food
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

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

10.0 ExcellentAnonymous, Apr 2025LGB - SMF
Read more Southwest reviews

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.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

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.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

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.

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.

It was a short flight so no food or entertainment….

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.

The plane was clean, the crew was friendly and helpful. It’s a low cost airline so there was no food, drinks or in flight entertainment but we didn’t expect any of these things. In the room for improvement department, they should install USB ports in seats to charge mobile devices.

I was surprised that all baggage, including carry on, were charged. Each additional bag went up in cost. Really disappointed in the additional costs.

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.