SJO - MDW

$165 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 10/30. 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.
1 adult
1 adult, Economy

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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Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San José to Midway

Tue, Sep 30 - Tue, Oct 7
Southwest Logo
8:50 am - 6:25 pmSJO-MDW
8h 35m1 stop
Southwest Logo
5:15 am - 11:40 amMDW-SJO
7h 25m1 stop
$335Southwest
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Tue, Oct 7 - Mon, Oct 20
Delta Logo
1:23 pm - 8:40 amSJO-MDW
18h 17m2 stops
Delta Logo
6:23 pm - 11:58 amMDW-SJO
18h 35m2 stops
$337Delta
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Wed, Nov 5 - Thu, Nov 6
Southwest Logo
2:15 pm - 10:10 pmSJO-MDW
7h 55m1 stop
Southwest Logo
5:50 am - 1:15 pmMDW-SJO
7h 25m1 stop
$339Southwest
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Fri, Oct 24 - Tue, Oct 28
Southwest Logo
12:55 pm - 11:55 pmSJO-MDW
10h 00m2 stops
Southwest Logo
8:05 pm - 11:50 amMDW-SJO
16h 45m2 stops
$340Southwest
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Fri, Nov 7 - Sun, Nov 16
Delta Logo
2:15 pm - 10:14 pmSJO-MDW
7h 59m1 stop
Delta Logo
10:47 am - 10:07 pmMDW-SJO
11h 20m1 stop
$341Delta
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Wed, Nov 5 - Thu, Nov 6
Southwest Logo
9:00 am - 9:05 pmSJO-MDW
12h 05m2 stops
Southwest Logo
5:50 am - 1:15 pmMDW-SJO
7h 25m1 stop
$344Southwest
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Mon, Oct 13 - Mon, Oct 20
Multiple Airlines Logo
8:50 am - 11:46 pmSJO-MDW
13h 56m1 stop
Multiple Airlines Logo
10:33 am - 10:40 pmMDW-SJO
13h 07m1 stop
$350Multiple Airlines
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Mon, Oct 13 - Mon, Oct 20
Multiple Airlines Logo
10:58 am - 11:46 pmSJO-MDW
11h 48m2 stops
Multiple Airlines Logo
10:33 am - 10:40 pmMDW-SJO
13h 07m1 stop
$365Multiple Airlines
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Sat, Jan 10 - Sat, Jan 17
Frontier Logo
2:58 pm - 11:25 pmSJO-MDW
8h 27m1 stop
Frontier Logo
6:00 am - 1:39 pmMDW-SJO
7h 39m1 stop
$489Frontier
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Sat, Jan 10 - Sat, Jan 17
Frontier Logo
2:58 pm - 11:25 pmSJO-MDW
8h 27m1 stop
Frontier Logo
6:00 am - 1:39 pmMDW-SJO
7h 39m1 stop
$521Frontier
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Everything you should know

Cheapest round-trip
$335
Southwest
Tue 9/30Tue 10/7
SJO - MDW • 1 stop
Cheapest one-way
$165
Multiple Airlines
Thu 10/30
SJO - MDW • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Booking Insights

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 seasonAugust
Cheapest flight$165
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 29% 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 $165 for a one-way ticket and $335 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.

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

Information on your arrival and departure airports

San José (SJO)
Midway (MDW)

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