MDW - SJO

$185 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 6/29. 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

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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Flights 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

Mon, Sep 22 - Sun, Sep 28
Southwest Logo
8:05 am - 6:55 pmMDW-SJO
11h 50m2 stops
Southwest Logo
12:35 pm - 9:15 pmSJO-MDW
7h 40m1 stop
$407Southwest
Find Deal
Mon, Sep 1 - Tue, Sep 30
Southwest Logo
8:05 am - 6:55 pmMDW-SJO
11h 50m2 stops
Southwest Logo
1:40 pm - 11:20 pmSJO-MDW
8h 40m1 stop
$414Southwest
Find Deal
Tue, Nov 11 - Fri, Nov 14
Southwest Logo
5:05 am - 1:15 pmMDW-SJO
8h 10m1 stop
Southwest Logo
9:00 am - 12:50 amSJO-MDW
15h 50m2 stops
$427Southwest
Find Deal
Sun, Jun 29 - Sun, Jul 13
Southwest Logo
5:15 am - 11:35 amMDW-SJO
7h 20m1 stop
Southwest Logo
1:15 pm - 11:55 pmSJO-MDW
9h 40m1 stop
$430Southwest
Find Deal
Tue, Nov 11 - Fri, Nov 14
Southwest Logo
10:50 am - 8:30 pmMDW-SJO
9h 40m2 stops
Southwest Logo
2:10 pm - 12:50 amSJO-MDW
10h 40m2 stops
$431Southwest
Find Deal
Mon, Sep 1 - Tue, Sep 30
Southwest Logo
8:05 am - 6:55 pmMDW-SJO
11h 50m2 stops
Southwest Logo
8:50 am - 7:20 pmSJO-MDW
9h 30m2 stops
$434Southwest
Find Deal
Thu, Jul 31 - Fri, Aug 8
 Logo
9:12 pm - 10:29 amMDW-SJO
14h 17m1 stop
 Logo
8:50 am - 11:17 pmSJO-MDW
13h 27m2 stops
Sun, Nov 9 - Sun, Nov 16
Delta Logo
6:00 am - 12:52 pmMDW-SJO
6h 52m1 stop
Delta Logo
2:17 pm - 9:44 pmSJO-MDW
7h 27m1 stop
$691Delta
Find Deal
Sun, Nov 9 - Sun, Nov 16
Delta Logo
6:00 am - 12:52 pmMDW-SJO
6h 52m1 stop
Delta Logo
2:17 pm - 9:44 pmSJO-MDW
7h 27m1 stop
$692Delta
Find Deal
Wed, Dec 3 - Sat, Dec 13
Delta Logo
10:35 am - 10:15 pmMDW-SJO
11h 40m1 stop
Delta Logo
2:17 pm - 9:44 pmSJO-MDW
7h 27m1 stop
$701Delta
Find Deal
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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.

What’s the cheapest day of the week to fly from Chicago Midway Airport to San José?

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

When flying from Chicago Midway Airport to San José, you should consider leaving on a Thursday and avoid Sundays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Thursdays and the most expensive ones on Saturdays.

What is the cheapest month to fly from Chicago Midway Airport to San José?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to San José, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to San José is August, where tickets cost $436 (return) on average. On the other hand, the most expensive months are June and January, where the average cost of round-trip tickets is $967 and $811 respectively.

Good to know

Low seasonMarch
High seasonFebruary
Cheapest flight$185
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 1% lower on average.
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 $185 for a one-way ticket and $407 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.

  • Which airline alliances offer flights from Chicago Midway Airport to San José?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and San José.

  • Which is the best airline for flights from Chicago to San José, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to San José are Southwest and Delta. With an average price for the route of $633 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $779 and an overall rating of 8.0.

  • 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.

Top airlines 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 4287 reviews
8.2Boarding
7.1Food
8.6Crew
8.0Comfort
7.6Entertainment
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

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

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