SJO - MDW

$162 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 11/16. 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
$336
Multiple Airlines
Tue 12/23Fri 1/2
SJO - MDW • 1 stop
Cheapest one-way
$162
Multiple Airlines
Sun 11/16
SJO - MDW • 2 stops
Top airlines
Delta
Cheapest • from $339 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+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
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

Tue, Dec 23 - Fri, Jan 2
Multiple Airlines Logo
7:45 am - 2:37 pmSJO-MDW
30h 52m1 stop
Multiple Airlines Logo
3:10 pm - 11:42 amMDW-SJO
20h 32m1 stop
$336Multiple Airlines
Find Deal
Fri, Dec 5 - Tue, Dec 9
Delta Logo
2:31 pm - 11:47 pmSJO-MDW
9h 16m1 stop
Delta Logo
9:34 am - 10:20 pmMDW-SJO
12h 46m2 stops
$339Delta
Find Deal
Sat, Jan 24 - Wed, Jan 28
Delta Logo
7:00 am - 3:40 pmSJO-MDW
8h 40m1 stop
Delta Logo
1:28 pm - 10:15 pmMDW-SJO
8h 47m2 stops
$343Delta
Find Deal
Tue, Dec 23 - Fri, Jan 2
Multiple Airlines Logo
12:39 pm - 9:58 pmSJO-MDW
9h 19m1 stop
Multiple Airlines Logo
3:10 pm - 11:42 amMDW-SJO
20h 32m1 stop
$362Multiple Airlines
Find Deal
Sat, Nov 8 - Tue, Nov 11
Southwest Logo
9:00 am - 8:25 pmSJO-MDW
11h 25m1 stop
Southwest Logo
5:05 am - 1:15 pmMDW-SJO
8h 10m1 stop
$366Southwest
Find Deal
Fri, Nov 7 - Sun, Nov 16
Delta Logo
2:15 pm - 10:14 pmSJO-MDW
7h 59m1 stop
Delta Logo
12:47 pm - 10:07 pmMDW-SJO
9h 20m1 stop
$368Delta
Find Deal
Thu, Dec 25 - Tue, Dec 30
Multiple Airlines Logo
12:39 pm - 9:58 pmSJO-MDW
9h 19m1 stop
Multiple Airlines Logo
6:14 am - 12:25 pmMDW-SJO
30h 11m2 stops
$380Multiple Airlines
Find Deal
Wed, Dec 24 - Wed, Dec 31
Frontier Logo
2:52 pm - 5:38 pmSJO-MDW
26h 46m1 stop
Frontier Logo
6:12 am - 1:42 pmMDW-SJO
7h 30m1 stop
$388Frontier
Find Deal
Fri, Jan 16 - Tue, Jan 20
Southwest Logo
1:45 pm - 10:25 pmSJO-MDW
8h 40m1 stop
Southwest Logo
8:55 am - 7:30 pmMDW-SJO
10h 35m1 stop
$410Southwest
Find Deal
Fri, Dec 26 - Wed, Dec 31
Frontier Logo
2:57 pm - 9:19 amSJO-MDW
18h 22m2 stops
Frontier Logo
6:12 am - 1:42 pmMDW-SJO
7h 30m1 stop
$447Frontier
Find Deal
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.

Good to know

Low seasonAugust
Cheapest flight$162
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 4% increase in price.
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 $162 for a one-way ticket and $336 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.
8.0
SouthwestOverall score based on 4243 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
Airline reviews

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.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

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.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

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

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

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

Information on your arrival and departure airports

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