SJO - MDW

$156 Find Cheap Flights from San José 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 José to Midway departing on 12/24. 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
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 José 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 José to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$299
Multiple Airlines
Fri 2/20Sun 3/1
SJO - MDW • 1 stop
Cheapest one-way
$156
Frontier
Wed 12/24
SJO - MDW • 1 stop
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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
Flight Deals

Cheap Flights from San José to Midway (SJO-MDW)

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

Fri, Feb 20 - Sun, Mar 1
Multiple Airlines Logo
12:35 pm - 2:55 pm
SJO
-
MDW
26h 20m1 stop
Multiple Airlines Logo
6:15 am - 3:30 pm
MDW
-
SJO
9h 15m1 stop
$299Multiple Airlines
Sat, Jan 10 - Sat, Jan 17
Frontier Logo
1:35 pm - 10:27 pm
SJO
-
MDW
8h 52m1 stop
Frontier Logo
6:10 am - 1:42 pm
MDW
-
SJO
7h 32m1 stop
$302Frontier
Sat, Jan 10 - Sat, Jan 17
Frontier Logo
1:35 pm - 10:27 pm
SJO
-
MDW
8h 52m1 stop
Frontier Logo
6:10 am - 1:42 pm
MDW
-
SJO
7h 32m1 stop
$333Frontier
Thu, Feb 5 - Sun, Feb 22
Delta Logo
2:31 pm - 10:22 pm
SJO
-
MDW
7h 51m1 stop
Delta Logo
12:46 pm - 10:02 pm
MDW
-
SJO
9h 16m1 stop
$345Delta
Wed, Feb 25 - Mon, Mar 2
Multiple Airlines Logo
3:05 pm - 1:56 pm
SJO
-
MDW
22h 51m2 stops
Multiple Airlines Logo
9:32 pm - 11:40 am
MDW
-
SJO
14h 08m1 stop
$363Multiple Airlines
Mon, Jan 12 - Mon, Jan 19
Multiple Airlines Logo
2:58 pm - 10:34 am
SJO
-
MDW
19h 36m1 stop
Multiple Airlines Logo
7:20 pm - 11:40 pm
MDW
-
SJO
28h 20m2 stops
$365Multiple Airlines
Wed, Jan 14 - Wed, Jan 28
Delta Logo
7:00 am - 10:07 pm
SJO
-
MDW
15h 07m1 stop
Delta Logo
10:46 am - 10:15 pm
MDW
-
SJO
11h 29m1 stop
$373Delta
Sat, Dec 27 - Mon, Jan 5
Frontier Logo
10:36 am - 9:04 pm
SJO
-
MDW
10h 28m1 stop
Frontier Logo
6:12 am - 1:42 pm
MDW
-
SJO
7h 30m1 stop
$375Frontier
Thu, Feb 5 - Sun, Feb 22
Southwest Logo
1:45 pm - 10:25 pm
SJO
-
MDW
8h 40m1 stop
Southwest Logo
6:05 am - 12:50 pm
MDW
-
SJO
6h 45m1 stop
$382Southwest
Sat, Jan 10 - Sun, Jan 18
Multiple Airlines Logo
1:35 pm - 10:59 pm
SJO
-
MDW
33h 24m2 stops
Multiple Airlines Logo
8:19 pm - 3:17 pm
MDW
-
SJO
18h 58m1 stop
$383Multiple Airlines
Booking Insights

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

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

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

Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Thursday and more expensive on a Saturday. On your return trip to San José, you should consider flying back on a Thursday, and avoid Sundays for better deals.

Find deals

Good to know

Low seasonAugust
Cheapest flight$156
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from San José to Chicago Midway Airport

When to book flights from San José to Midway

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

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

    In the last 3 days, the lowest price for a flight from San José to Chicago Midway Airport was $156 for a one-way ticket and $299 for a round-trip.

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

    Yes, you'll most likely have to show a valid passport before boarding the plane in San José and on arrival in Chicago Midway Airport.

  • Which airports will I be using when flying from San José to Chicago Midway Airport?

    San José and Chicago Midway Airport are both served by 1 main airport. You will leave San José from San José Juan Santamaria Intl and will be arriving at Chicago Midway.

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

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from San José 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 José 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 José 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 José 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 José 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 José with another airline. Booking your flights between San José 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 José 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 José up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from San José to Midway

 
See real verified KAYAK customer reviews for airlines flying from San José 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 José 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.
7.9
SouthwestOverall score based on 4250 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

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.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

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

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

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

Information on your arrival and departure airports

San José (SJO)
Midway (MDW)