SJO - MDW

$157 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 3/7. 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
$335
Delta
Tue 3/17Tue 3/24
SJO - MDW • 1 stop
Cheapest one-way
$157
Multiple Airlines
Sat 3/7
SJO - MDW • 1 stop
Top airlines
Delta
Cheapest • from $335 (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, Mar 17 - Tue, Mar 24
Delta Logo
7:00 am - 10:31 pm
SJO
-
MDW
14h 31m
1 stop
Delta Logo
9:35 am - 9:15 pm
MDW
-
SJO
12h 40m
2 stops
$335Delta
Wed, May 6 - Wed, May 13
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
$356Southwest
Fri, Mar 13 - Tue, Mar 17
Multiple Airlines Logo
11:38 am - 11:51 pm
SJO
-
MDW
11h 13m
1 stop
Multiple Airlines Logo
6:00 am - 3:30 pm
MDW
-
SJO
10h 30m
2 stops
$358Multiple Airlines
Sat, Feb 14 - Sat, Feb 21
Delta Logo
2:25 pm - 10:31 pm
SJO
-
MDW
8h 06m
1 stop
Delta Logo
6:00 am - 10:02 pm
MDW
-
SJO
16h 02m
1 stop
$359Delta
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
1:15 pm - 9:50 pm
SJO
-
MDW
8h 35m
1 stop
Southwest Logo
11:35 am - 7:30 pm
MDW
-
SJO
7h 55m
1 stop
$361Southwest
Tue, May 5 - Tue, May 12
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
Southwest Logo
6:00 am - 12:10 pm
MDW
-
SJO
7h 10m
1 stop
$383Southwest
Tue, May 5 - Tue, May 12
Southwest Logo
9:00 am - 7:45 pm
SJO
-
MDW
9h 45m
2 stops
Southwest Logo
6:00 am - 12:10 pm
MDW
-
SJO
7h 10m
1 stop
$387Southwest
Thu, May 7 - Tue, May 12
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
6:00 am - 12:10 pm
MDW
-
SJO
7h 10m
1 stop
$392Southwest
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
1:15 pm - 9:50 pm
SJO
-
MDW
8h 35m
1 stop
Southwest Logo
11:35 am - 7:30 pm
MDW
-
SJO
7h 55m
1 stop
$393Southwest
Mon, Mar 30 - Mon, Apr 6
Multiple Airlines Logo
12:19 pm - 3:02 pm
SJO
-
MDW
25h 43m
2 stops
Multiple Airlines Logo
9:04 pm - 10:42 am
MDW
-
SJO
14h 38m
1 stop
$402Multiple 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.

Which airlines provide the cheapest flights from San José to Chicago Midway Airport?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from San José to Chicago Midway Airport were found on Delta ($335) and Southwest ($356).

Find deals

Good to know

Low seasonMarch
Cheapest flight$157
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 11% 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 $157 for a one-way ticket and $335 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 4273 reviews
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

10.0 ExcellentAnonymous, Feb 2026
MSY - PHX
Read more Southwest reviews

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

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)