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SJO - MDW

$184 Find cheap flights from San José to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San José to Midway departing on 6/5. 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
Thu 6/13
Thu 6/20

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San José to Chicago, 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 San José to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 41,771,603 times on KAYAK, and here is why:

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Cheap flight deals from San José to Midway (SJO-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San José to Midway 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.
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12:59 am - 3:37 pmSJO-MDW
13h 38m2 stops
7:35 am - 8:46 amMDW-SJO
26h 11m1 stop
$257
Find Deal
Mon, May 20 - Tue, May 28
1:42 pm - 6:54 amSJO-MDW
16h 12m1 stop
9:12 pm - 12:47 pmMDW-SJO
16h 35m2 stops
$337
Find Deal
Tue, May 21 - Thu, May 30
4:15 am - 6:28 pmSJO-MDW
13h 13m2 stops
7:20 am - 8:46 amMDW-SJO
26h 26m1 stop
$373
Find Deal
Sun, May 26 - Sat, Jun 1
12:59 am - 12:45 amSJO-MDW
22h 46m2 stops
7:20 am - 8:46 amMDW-SJO
26h 26m1 stop
$377
Find Deal
Sat, May 25 - Sat, Jun 1
9:40 am - 8:49 pmSJO-MDW
10h 09m1 stop
6:00 am - 8:25 amMDW-SJO
27h 25m1 stop
$423Frontier
Find Deal
Thu, Jul 18 - Sat, Jul 20
9:19 am - 10:55 amSJO-MDW
24h 36m1 stop
6:00 am - 8:25 amMDW-SJO
27h 25m1 stop
$540Frontier
Find Deal
Thu, Jul 4 - Sat, Jul 6
9:16 am - 2:41 pmSJO-MDW
28h 25m1 stop
7:53 am - 8:16 amMDW-SJO
25h 23m1 stop
$546Frontier
Find Deal
Sun, May 26 - Sat, Jun 1
1:07 pm - 9:46 pmSJO-MDW
7h 39m1 stop
9:34 am - 8:27 pmMDW-SJO
11h 53m2 stops
$776Delta
Find Deal
Mon, Jun 10 - Fri, Jun 21
7:00 am - 9:46 pmSJO-MDW
13h 46m1 stop
12:35 pm - 8:37 pmMDW-SJO
9h 02m1 stop
$823Delta
Find Deal
Sat, Jul 13 - Sat, Jul 20
1:13 pm - 9:47 pmSJO-MDW
7h 34m1 stop
6:00 am - 11:53 amMDW-SJO
6h 53m1 stop
$850Delta
Find Deal
Wed, Aug 7 - Wed, Aug 14

Flights from San José to Midway - Travel Insights & Trends

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from San José, San José Province to Chicago Midway Airport, 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 San José, San José Province to Chicago Midway Airport is August, where tickets cost $376 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is $1,509 and $1,199 respectively.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($195) and Delta ($562). The cheapest round-trip tickets were found on Frontier ($423) and Delta ($776).

Good to know

Low season

May

High season

October

Cheapest flight

$184
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from San José to Chicago Midway Airport

When to book flights from San José to Midway

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

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

    In the last 3 days, the lowest price for a flight from San José, San José Province to Chicago Midway Airport was $184 for a one-way ticket and $257 for a round-trip.

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

    Yes, you'll most likely have to show a valid passport before boarding the plane in San José and on arrival in Chicago Midway Airport.

  • Which airports will I be using when flying from San José to Chicago Midway Airport?

    San José and Chicago Midway Airport are both served by 1 main airport. You will leave San José from San José Juan Santamaria Intl and will be arriving at Chicago Midway.

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

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

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

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

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

    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 San José to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San José to Chicago Midway Airport?

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

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

    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 Chicago Midway Airport from San José up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Book cheap flights from San José to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from San José to Chicago found on KAYAK in the last 72 hours.
6/5Wed
2 stops
22h 21mSJO-MDW
$184
6/9Sun
1 stopFrontier
28h 11mSJO-MDW
$195
6/6Thu
2 stops
30h 35mSJO-MDW
$200
6/6Thu
1 stopFrontier
28h 15mSJO-MDW
$216
6/6Thu
3 stops
15h 46mSJO-MDW
$217
6/21Fri
1 stop
17h 13mSJO-MDW
$254
6/21Fri
1 stop
17h 13mSJO-MDW
$256
5/25Sat
1 stopDelta
7h 50mSJO-MDW
$562
6/20Thu
3 stopsAeromexico
19h 34mSJO-MDW
$634
6/29Sat
1 stopDelta
7h 39mSJO-MDW
$667

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Last minute flights from San José to Midway

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 San José to Chicago that are departing in the next 10 days.
5/18Sat
multi-stop
9h 02mSJO-MDW
5/26Sun
multi-stop
26h 01mMDW-SJO
$438
5/18Sat
multi-stop
9h 02mSJO-MDW
5/21Tue
multi-stop
23h 30mMDW-SJO
$446
5/18Sat
multi-stop
9h 02mSJO-MDW
5/21Tue
multi-stop
26h 11mMDW-SJO
$450
5/17Fri
multi-stop
26h 45mSJO-MDW
5/21Tue
multi-stop
12h 45mMDW-SJO
$465
5/18Sat
multi-stop
10h 36mSJO-MDW
5/26Sun
multi-stop
26h 01mMDW-SJO
$501
5/17Fri
multi-stopDelta
7h 50mSJO-MDW
5/21Tue
multi-stopDelta
8h 31mMDW-SJO
$1,630
5/18Sat
multi-stopDelta
7h 50mSJO-MDW
5/28Tue
multi-stopDelta
11h 41mMDW-SJO
$2,386

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San José - Chicago Midway Airport Flights

Departure:

San José (undefined)Costa Rica

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - San José

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