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 7/26. 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.
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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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Cheap Flights from Midway to San José

 
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.

Recent round-trip flight deals from Midway to San José

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to San José.
Discover the best prices for you by selecting your travel dates on KAYAK.
 Logo
9:12 pm - 10:27 amMDW-SJO
14h 15m1 stop
 Logo
6:05 pm - 8:17 pmSJO-MDW
25h 12m2 stops
Mon, Jun 2 - Thu, Jun 5
 Logo
9:12 pm - 10:27 amMDW-SJO
14h 15m1 stop
 Logo
8:46 am - 8:17 pmSJO-MDW
10h 31m2 stops
Mon, Jun 2 - Thu, Jun 5
 Logo
6:35 am - 11:33 amMDW-SJO
29h 58m2 stops
 Logo
5:10 pm - 7:31 pmSJO-MDW
25h 21m1 stop
Tue, May 27 - Tue, Jun 3
Delta Logo
6:00 am - 11:48 amMDW-SJO
6h 48m1 stop
Delta Logo
1:18 pm - 9:44 pmSJO-MDW
7h 26m1 stop
$446Delta
Find Deal
Wed, Sep 3 - Mon, Sep 8
Southwest Logo
9:15 am - 6:55 pmMDW-SJO
10h 40m2 stops
Southwest Logo
1:40 pm - 11:20 pmSJO-MDW
8h 40m1 stop
$451Southwest
Find Deal
Thu, Sep 25 - Tue, Sep 30
Southwest Logo
8:30 am - 7:05 pmMDW-SJO
11h 35m1 stop
Southwest Logo
12:55 pm - 11:15 pmSJO-MDW
9h 20m1 stop
$462Southwest
Find Deal
Sun, Sep 21 - Mon, Oct 6
Delta Logo
6:00 am - 11:53 amMDW-SJO
6h 53m1 stop
Delta Logo
1:18 pm - 9:44 pmSJO-MDW
7h 26m1 stop
$484Delta
Find Deal
Thu, Sep 25 - Tue, Sep 30
Southwest Logo
11:10 am - 7:40 pmMDW-SJO
9h 30m1 stop
Southwest Logo
1:40 pm - 1:05 amSJO-MDW
10h 25m1 stop
$485Southwest
Find Deal
Mon, Jun 2 - Thu, Jun 5
Southwest Logo
11:40 am - 7:40 pmMDW-SJO
9h 00m1 stop
Southwest Logo
8:45 am - 9:25 pmSJO-MDW
11h 40m2 stops
$490Southwest
Find Deal
Mon, Jul 28 - Fri, Aug 1
Delta Logo
6:00 am - 11:56 amMDW-SJO
6h 56m1 stop
Delta Logo
1:21 pm - 12:29 pmSJO-MDW
22h 08m2 stops
$650Delta
Find Deal
Sat, Jul 26 - Mon, Aug 4
Useful Info

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 $419 (return) on average. On the other hand, the most expensive months are June and March, where the average cost of round-trip tickets is $1,193 and $990 respectively.

Good to know

Low seasonDecember
High seasonFebruary
Cheapest flight$169
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 6% 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 $169 for a one-way ticket and $374 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 $644 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 $886 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 4294 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
8.6Crew
7.1Food
Airline reviews

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

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

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

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

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

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