MDW - SJO

$169 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 6/20. 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
$438
Delta
Tue 9/29Thu 10/15
MDW - SJO • 1 stop
Cheapest one-way
$178
Frontier
Sat 6/20
MDW - SJO • 2 stops
Top airlines
Delta
Cheapest • from $438 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Midway and San José. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Houston (HOU)
Cheapest • Avg $503 (round-trip)
Houston (HOU)
Shortest trip • 7h 00m (one-way)
Insights
Insights
Insights
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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 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

Tue, Sep 29 - Thu, Oct 15
Delta Logo
6:00 am - 11:54 am
MDW
-
SJO
6h 54m
1 stop
Delta Logo
1:23 pm - 9:45 pm
SJO
-
MDW
7h 22m
1 stop
$438Delta
Mon, Oct 5 - Wed, Oct 14
Delta Logo
5:59 pm - 11:58 am
MDW
-
SJO
18h 59m
2 stops
Delta Logo
1:23 pm - 12:33 pm
SJO
-
MDW
22h 10m
2 stops
$443Delta
Fri, Aug 14 - Wed, Aug 19
Delta Logo
6:00 am - 11:56 am
MDW
-
SJO
6h 56m
1 stop
Delta Logo
1:21 pm - 8:42 am
SJO
-
MDW
18h 21m
2 stops
$445Delta
Mon, Aug 24 - Wed, Sep 23
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
2 stops
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
$484Southwest
Mon, Aug 24 - Wed, Sep 23
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
2 stops
Southwest Logo
9:00 am - 9:50 pm
SJO
-
MDW
11h 50m
2 stops
$488Southwest
Sun, May 24 - Thu, May 28
Southwest Logo
1:10 pm - 7:00 pm
MDW
-
SJO
6h 50m
1 stop
Southwest Logo
9:00 am - 8:15 pm
SJO
-
MDW
10h 15m
2 stops
$492Southwest
Mon, Aug 10 - Mon, Aug 17
Delta Logo
6:05 am - 11:49 am
MDW
-
SJO
6h 44m
1 stop
Delta Logo
1:14 pm - 10:36 pm
SJO
-
MDW
8h 22m
1 stop
$502Delta
Sat, Aug 8 - Fri, Aug 21
Delta Logo
6:05 am - 1:03 pm
MDW
-
SJO
7h 58m
1 stop
Delta Logo
1:14 pm - 10:36 pm
SJO
-
MDW
8h 22m
1 stop
$504Delta
Fri, Aug 14 - Thu, Aug 20
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
2 stops
Southwest Logo
9:00 am - 9:30 pm
SJO
-
MDW
11h 30m
1 stop
$506Southwest
Mon, Oct 5 - Tue, Oct 13
Delta Logo
5:59 pm - 11:58 am
MDW
-
SJO
18h 59m
2 stops
Delta Logo
1:23 pm - 9:45 pm
SJO
-
MDW
7h 22m
1 stop
$507Delta
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 ($438) and Southwest ($484).

Find deals

Good to know

Cheapest flight$178
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 $178 for a one-way ticket and $438 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.
7.9
SouthwestOverall score based on 4301 reviews
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

10.0 ExcellentRobert, May 2026
LAS - SFO
Read more Southwest reviews

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

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)