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SJO - MDW

$188 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 4/30. 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 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
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Cheap Flights from San José to Midway

 
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.

Recent round-trip flight deals from San José to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from San José to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
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Southwest Logo
1:40 pm - 12:05 amSJO-MDW
9h 25m1 stop
Southwest Logo
5:05 am - 12:45 pmMDW-SJO
8h 40m1 stop
$426Southwest
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Thu, Sep 11 - Mon, Sep 15
Southwest Logo
8:50 am - 10:00 pmSJO-MDW
12h 10m2 stops
Southwest Logo
6:35 am - 12:45 pmMDW-SJO
7h 10m1 stop
$441Southwest
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Thu, Sep 18 - Mon, Sep 22
Southwest Logo
1:35 pm - 11:30 pmSJO-MDW
8h 55m1 stop
Southwest Logo
6:10 am - 12:10 pmMDW-SJO
7h 00m1 stop
$444Southwest
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Sat, Apr 26 - Sat, May 10
Southwest Logo
1:40 pm - 12:05 amSJO-MDW
9h 25m1 stop
Southwest Logo
10:10 am - 6:55 pmMDW-SJO
9h 45m1 stop
$447Southwest
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Fri, Aug 15 - Sat, Aug 23
Frontier Logo
1:15 pm - 9:03 amSJO-MDW
18h 48m1 stop
Frontier Logo
6:00 am - 12:37 pmMDW-SJO
7h 37m1 stop
$486Frontier
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Sat, May 31 - Sat, Jun 14
Frontier Logo
1:47 pm - 11:22 pmSJO-MDW
8h 35m1 stop
Frontier Logo
6:00 am - 12:37 pmMDW-SJO
7h 37m1 stop
$489Frontier
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Sat, Jun 14 - Sat, Jun 21
Delta Logo
1:20 pm - 10:22 pmSJO-MDW
8h 02m1 stop
Delta Logo
6:00 am - 11:59 amMDW-SJO
6h 59m1 stop
$502Delta
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Sat, May 3 - Sat, May 10
Delta Logo
1:18 pm - 9:44 pmSJO-MDW
7h 26m1 stop
Delta Logo
6:00 am - 11:53 amMDW-SJO
6h 53m1 stop
$505Delta
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Fri, Sep 26 - Wed, Oct 1
Logo
11:35 am - 9:24 amSJO-MDW
20h 49m1 stop
Logo
12:46 pm - 10:24 amMDW-SJO
22h 38m1 stop
$551
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Wed, Apr 16 - Sun, Apr 20
Logo
12:55 am - 7:35 pmSJO-MDW
17h 40m2 stops
Logo
12:46 pm - 10:24 amMDW-SJO
22h 38m1 stop
$565
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Tue, Apr 15 - Sun, Apr 20

KAYAK's insights & trends for San José to Midway flights

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

The average price of all round-trip flights from San José to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Thursday and more expensive on a Saturday. On your return trip to San José, you should consider flying back on a Thursday, and avoid Sundays for better deals.
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Good to know

Low season

March

High season

October

Cheapest flight

$188
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 2% increase in price.
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 to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from San José to Chicago Midway Airport was $188 for a one-way ticket and $426 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.

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

Information on your arrival and departure airports

Midway (MDW)
San José (SJO)

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