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MDW - SJO

$112 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 5/21. 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
0 bags
vie. 6/7
vie. 6/14

Search 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
In the last 7 days travelers have searched 43,968,530 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
7:00 am - 8:16 amMDW-SJO
26h 16m1 stop
9:40 am - 8:17 pmSJO-MDW
9h 37m1 stop
$251Frontier
Find Deal
mié., may. 15 - jue., may. 30
7:00 am - 8:16 amMDW-SJO
26h 16m1 stop
9:40 am - 8:17 pmSJO-MDW
9h 37m1 stop
$256Frontier
Find Deal
mié., may. 15 - jue., may. 30
7:35 am - 8:46 amMDW-SJO
26h 11m1 stop
1:42 pm - 6:54 amSJO-MDW
16h 12m1 stop
mar., may. 21 - mar., may. 28
7:00 am - 8:10 amMDW-SJO
26h 10m1 stop
9:40 am - 8:49 pmSJO-MDW
10h 09m1 stop
$349Frontier
Find Deal
sáb., jun. 29 - jue., jul. 18
8:53 pm - 12:45 pmMDW-SJO
16h 52m1 stop
1:42 pm - 7:55 amSJO-MDW
17h 13m1 stop
dom., jun. 9 - vie., jun. 14
7:35 am - 8:46 amMDW-SJO
26h 11m1 stop
12:59 am - 3:37 pmSJO-MDW
13h 38m2 stops
mar., may. 21 - lun., may. 27
1:05 pm - 8:08 pmMDW-SJO
8h 03m1 stop
1:13 pm - 9:47 pmSJO-MDW
7h 34m1 stop
$661Delta
Find Deal
vie., jul. 19 - sáb., ago. 24
10:11 am - 8:08 pmMDW-SJO
10h 57m1 stop
7:00 am - 9:41 pmSJO-MDW
13h 41m1 stop
$676Delta
Find Deal
vie., jul. 19 - sáb., jul. 27
9:34 am - 8:27 pmMDW-SJO
11h 53m2 stops
7:00 am - 9:41 pmSJO-MDW
13h 41m1 stop
$681Delta
Find Deal
jue., jun. 27 - sáb., jul. 20
12:42 pm - 8:13 pmMDW-SJO
8h 31m1 stop
1:14 pm - 10:01 pmSJO-MDW
7h 47m1 stop
$784Delta
Find Deal
jue., may. 30 - mar., jun. 4

Flights from Midway to San José - Travel Insights & Trends

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to San José, San José Province, 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, San José Province is August, where tickets cost $422 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is $748 and $714 respectively.

How far in advance should I book a flight from Chicago Midway Airport to San José, San José Province?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to San José, San José Province, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to San José, San José Province, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 33 days before departure.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago Midway Airport to San José found by KAYAK users in the last 72 hours was for $251 on Frontier, followed by Delta ($661). One-way flight deals have also been found from as low as $168 on Frontier and from $373 on Delta.

Good to know

Low season

May

High season

April

Cheapest flight

$112
Best time to beat the crowds with an average 65% drop in price.
Most popular time to fly and prices are also 2% 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, San José Province?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to San José, San José Province was $112 for a one-way ticket and $251 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.

  • 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.

See more FAQs

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
DeltaOverall score based on 10789 reviews
7.9Comfort
8.2Boarding
8.6Crew
7.4Food
8.0Entertainment
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

Book cheap flights from Chicago to San José

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to San José found on KAYAK in the last 72 hours.
5/21mar.
1 stop
26h 11mMDW-SJO
$112
5/21mar.
2 stops
22h 28mMDW-SJO
$113
5/20lun.
2 stops
17h 01mMDW-SJO
$137
6/24lun.
3 stops
15h 48mMDW-SJO
$150
5/19dom.
1 stop
26h 01mMDW-SJO
$159
6/5mié.
1 stopFrontier
19h 23mMDW-SJO
$168
5/20lun.
1 stop
19h 17mMDW-SJO
$171
7/9mar.
1 stopDelta
10h 57mMDW-SJO
$373
7/26vie.
1 stopDelta
6h 53mMDW-SJO
$378
7/1lun.
1 stopDelta
10h 46mMDW-SJO
$462

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Last minute flights from Midway to San José

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to San José that are departing in the next 10 days.
5/13lun.
multi-stop
18h 37mMDW-SJO
5/17vie.
multi-stop
26h 45mSJO-MDW
$357
5/11sáb.
multi-stop
16h 55mMDW-SJO
5/20lun.
multi-stop
29h 01mSJO-MDW
$383
5/12dom.
multi-stop
16h 43mMDW-SJO
5/17vie.
multi-stop
26h 45mSJO-MDW
$385
5/13lun.
multi-stop
19h 52mMDW-SJO
5/17vie.
multi-stop
26h 45mSJO-MDW
$419
5/13lun.
multi-stop
18h 37mMDW-SJO
5/19dom.
multi-stop
11h 09mSJO-MDW
$433
5/12dom.
multi-stop
15h 50mMDW-SJO
5/18sáb.
multi-stop
9h 02mSJO-MDW
$456
5/11sáb.
multi-stop
16h 55mMDW-SJO
5/22mié.
multi-stop
11h 34mSJO-MDW
$482
5/11sáb.
multi-stop
13h 16mMDW-SJO
5/20lun.
multi-stop
29h 01mSJO-MDW
$489
5/9jue.
multi-stopDelta
12h 28mMDW-SJO
5/31vie.
multi-stopDelta
14h 01mSJO-MDW
$1,094
5/11sáb.
multi-stopDelta
10h 12mMDW-SJO
5/21mar.
multi-stopDelta
14h 01mSJO-MDW
$1,178

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Chicago Midway Airport - San José Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

San José (SJO)Costa Rica

Return flight deals:

San José - Chicago Midway Airport

Cabin classes: