MDW - SJO

$149 Find Cheap Flights from Chicago Midway Airport to San José

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 José departing on 3/8. 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 San José

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José, 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 José, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$331
Multiple Airlines
Sat 2/28Sun 3/8
MDW - SJO • 1 stop
Cheapest one-way
$149
Multiple Airlines
Sun 3/8
MDW - SJO • 1 stop
Top airlines
Delta
Cheapest • from $337 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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We hope you love your trip to San José!
Flight Deals
Booking Insights
Flight Deals

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

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

Sat, Feb 28 - Sun, Mar 8
Multiple Airlines Logo
8:00 am - 11:40 am
MDW
-
SJO
27h 40m
1 stop
Multiple Airlines Logo
11:35 am - 1:08 pm
SJO
-
MDW
24h 33m
1 stop
$331Multiple Airlines
Tue, Mar 3 - Tue, Mar 10
Delta Logo
10:49 am - 10:02 pm
MDW
-
SJO
11h 13m
1 stop
Delta Logo
7:00 am - 10:31 pm
SJO
-
MDW
14h 31m
1 stop
$337Delta
Tue, Mar 3 - Tue, Mar 10
Delta Logo
9:34 am - 10:02 pm
MDW
-
SJO
12h 28m
2 stops
Delta Logo
7:00 am - 10:31 pm
SJO
-
MDW
14h 31m
1 stop
$342Delta
Mon, Mar 9 - Mon, Mar 16
Multiple Airlines Logo
6:00 am - 6:55 pm
MDW
-
SJO
13h 55m
2 stops
Multiple Airlines Logo
11:38 am - 8:53 pm
SJO
-
MDW
8h 15m
1 stop
$344Multiple Airlines
Mon, Mar 9 - Mon, Mar 16
Multiple Airlines Logo
9:51 pm - 10:40 am
MDW
-
SJO
13h 49m
1 stop
Multiple Airlines Logo
11:38 am - 8:53 pm
SJO
-
MDW
8h 15m
1 stop
$345Multiple Airlines
Mon, Mar 9 - Tue, Mar 17
Delta Logo
10:45 am - 9:15 pm
MDW
-
SJO
11h 30m
1 stop
Delta Logo
7:00 am - 10:31 pm
SJO
-
MDW
14h 31m
1 stop
$348Delta
Mon, Mar 9 - Tue, Mar 17
Delta Logo
1:10 pm - 9:15 pm
MDW
-
SJO
9h 05m
2 stops
Delta Logo
7:00 am - 5:22 pm
SJO
-
MDW
9h 22m
1 stop
$353Delta
Sat, Feb 28 - Sat, Mar 7
Multiple Airlines Logo
8:00 am - 11:40 am
MDW
-
SJO
27h 40m
1 stop
Multiple Airlines Logo
12:35 pm - 9:45 pm
SJO
-
MDW
9h 10m
1 stop
$355Multiple Airlines
Sat, Feb 28 - Sat, Mar 7
Multiple Airlines Logo
9:15 am - 11:30 pm
MDW
-
SJO
14h 15m
2 stops
Multiple Airlines Logo
12:35 pm - 9:45 pm
SJO
-
MDW
9h 10m
1 stop
$376Multiple Airlines
Tue, May 12 - Tue, May 19
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
$386Southwest
Booking Insights

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

Get data-powered insights and trends into flights from Midway to San José to help you find the cheapest flights, the best time to fly and much more.

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

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 Chicago Midway Airport to San José were found on Delta ($337) and Southwest ($386).

Find deals

Good to know

Cheapest flight$149
Flight from Chicago Midway Airport to San José

When to book flights from Midway to San José

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

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to San José was $149 for a one-way ticket and $331 for a round-trip.

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

    A passport is required to fly from Chicago Midway Airport to San José.

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

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

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

    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 José.

  • 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 José?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San José 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 José?

    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 José with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SJO 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 José?

    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 José from Chicago Midway Airport 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 Midway to San José

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San José. 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 José? 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
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
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 Midway to San José

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
San José (SJO)