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SJO - MDW

$132 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 3/11. 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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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 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.

Recent round-trip flight deals from San José to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from San José to Midway.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
12:50 am - 3:46 pmSJO-MDW
13h 56m2 stops
12:46 pm - 10:50 amMDW-SJO
23h 04m1 stop
$251
Find Deal
Tue, Mar 25 - Wed, Apr 2
12:50 am - 3:46 pmSJO-MDW
13h 56m2 stops
12:46 pm - 10:50 amMDW-SJO
23h 04m1 stop
$258
Find Deal
Tue, Mar 25 - Wed, Apr 2
11:55 am - 11:24 pmSJO-MDW
10h 29m1 stop
6:00 am - 10:40 pmMDW-SJO
17h 40m1 stop
$328
Find Deal
Tue, Apr 8 - Tue, Apr 15
11:30 am - 10:39 pmSJO-MDW
10h 09m1 stop
12:46 pm - 10:50 amMDW-SJO
23h 04m1 stop
$335
Find Deal
Thu, Mar 27 - Wed, Apr 2
1:42 pm - 5:49 pmSJO-MDW
27h 07m1 stop
6:44 pm - 12:22 pmMDW-SJO
18h 38m1 stop
$441Frontier
Find Deal
Sat, Jun 7 - Fri, Jun 13
1:42 pm - 11:55 pmSJO-MDW
9h 13m1 stop
9:12 pm - 12:22 pmMDW-SJO
16h 10m2 stops
$442Frontier
Find Deal
Sat, Jun 7 - Fri, Jun 13
1:10 pm - 11:35 pmSJO-MDW
9h 25m1 stop
8:45 am - 7:40 pmMDW-SJO
11h 55m1 stop
$523Southwest
Find Deal
Fri, May 16 - Tue, May 20
1:21 pm - 10:23 pmSJO-MDW
8h 02m1 stop
12:51 pm - 9:24 pmMDW-SJO
9h 33m1 stop
$524Delta
Find Deal
Tue, Mar 18 - Wed, Mar 26
8:45 am - 10:00 pmSJO-MDW
12h 15m2 stops
10:00 am - 7:40 pmMDW-SJO
10h 40m2 stops
$527Southwest
Find Deal
Thu, May 15 - Wed, May 21
2:19 pm - 10:20 pmSJO-MDW
8h 01m1 stop
9:25 am - 9:24 pmMDW-SJO
12h 59m2 stops
$572Delta
Find Deal
Wed, Mar 5 - Mon, Mar 10

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’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.

Good to know

Low season

August

High season

October

Cheapest flight

$132
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 13% 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 to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from San José to Chicago Midway Airport was $132 for a one-way ticket and $251 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

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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