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Cheap flights from Chicago Midway Airport to San José, San José Province from $162

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San José, San José Province departing on 12/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to San José that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to San José.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to San José? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to San José, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to San José

Find recent round-trip train or bus tickets from Chicago Midway Airport to San José.

All round-trip flight deals to San José

The cheapest plane tickets to San José found on KAYAK recently.
8:50 am - 11:31 amMDW-SJO
26h 41m1 stop
1:24 pm - 10:45 pmSJO-MDW
33h 21m2 stops
Mon, Dec 2 - Sat, Dec 7
5:35 am - 12:55 pmMDW-SJO
7h 20m1 stop
8:45 am - 10:20 pmSJO-MDW
12h 35m2 stops
$518Southwest
Find Deal
Sun, Mar 2 - Wed, Mar 12
8:40 am - 8:40 pmMDW-SJO
12h 00m2 stops
1:40 pm - 8:40 amSJO-MDW
19h 00m2 stops
$522Southwest
Find Deal
Fri, Dec 6 - Thu, Dec 12
5:45 am - 12:55 pmMDW-SJO
7h 10m1 stop
9:55 am - 6:50 pmSJO-MDW
8h 55m2 stops
$538Southwest
Find Deal
Wed, Feb 26 - Tue, Mar 4
7:15 am - 8:40 pmMDW-SJO
13h 25m2 stops
9:55 am - 7:25 pmSJO-MDW
9h 30m2 stops
$543Southwest
Find Deal
Wed, Jan 8 - Fri, Jan 31
8:40 am - 8:40 pmMDW-SJO
12h 00m2 stops
9:55 am - 6:50 pmSJO-MDW
8h 55m1 stop
$548Southwest
Find Deal
Fri, Dec 6 - Thu, Dec 12
6:00 am - 12:48 pmMDW-SJO
6h 48m1 stop
7:00 am - 5:01 pmSJO-MDW
10h 01m2 stops
$625Delta
Find Deal
Sat, Dec 7 - Wed, Dec 11
3:19 pm - 9:53 pmMDW-SJO
6h 34m1 stop
7:00 am - 4:12 pmSJO-MDW
9h 12m1 stop
$636Delta
Find Deal
Mon, Dec 2 - Tue, Dec 10
9:44 pm - 8:25 amMDW-SJO
10h 41m1 stop
9:40 am - 8:49 pmSJO-MDW
10h 09m1 stop
$808Frontier
Find Deal
Sat, Mar 8 - Thu, Mar 13
8:12 am - 9:25 amMDW-SJO
25h 13m1 stop
9:40 am - 8:49 pmSJO-MDW
10h 09m1 stop
$822Frontier
Find Deal
Wed, Mar 5 - Sun, Mar 16
4:27 pm - 12:53 amMDW-SJO
32h 26m2 stops
Thu, Dec 5
8:12 am - 12:59 amMDW-SJO
16h 47m2 stops
Wed, Feb 26
8:25 am - 10:18 amMDW-SJO
25h 53m1 stop
$208Frontier
Find Deal
Wed, Jan 1
8:12 am - 12:59 amMDW-SJO
16h 47m3 stops
Wed, Feb 26
12:36 pm - 11:28 amMDW-SJO
22h 52m2 stops
Mon, Dec 9
5:45 am - 12:55 pmMDW-SJO
7h 10m1 stop
$249Southwest
Find Deal
Wed, Feb 26
8:40 am - 8:40 pmMDW-SJO
12h 00m2 stops
$289Southwest
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Wed, Dec 4
10:38 am - 9:57 pmMDW-SJO
11h 19m1 stop
$297Delta
Find Deal
Tue, Dec 10
6:00 am - 12:48 pmMDW-SJO
6h 48m1 stop
$299Delta
Find Deal
Tue, Dec 10
9:44 pm - 8:25 amMDW-SJO
10h 41m1 stop
$323Frontier
Find Deal
Sat, Mar 8
12:51 pm - 11:31 amMDW-SJO
22h 40m2 stops
12:26 pm - 9:35 amSJO-MDW
21h 09m1 stop
Sun, Nov 24 - Tue, Nov 26
1:35 pm - 8:40 pmMDW-SJO
7h 05m1 stop
1:40 pm - 1:00 amSJO-MDW
11h 20m1 stop
$744Southwest
Find Deal
Sun, Nov 24 - Tue, Nov 26
8:50 am - 8:40 pmMDW-SJO
11h 50m2 stops
9:55 am - 8:35 pmSJO-MDW
10h 40m2 stops
$748Southwest
Find Deal
Sun, Nov 24 - Tue, Nov 26
1:35 pm - 8:40 pmMDW-SJO
7h 05m1 stop
1:40 pm - 7:50 amSJO-MDW
18h 10m2 stops
$894Southwest
Find Deal
Fri, Nov 22 - Fri, Nov 29
1:35 pm - 8:40 pmMDW-SJO
7h 05m1 stop
9:55 am - 5:30 pmSJO-MDW
7h 35m1 stop
$940Southwest
Find Deal
Fri, Nov 22 - Fri, Nov 29
12:15 pm - 7:25 amMDW-SJO
19h 10m2 stops
12:26 pm - 7:55 amSJO-MDW
19h 29m1 stop
$1,268
Find Deal
Fri, Nov 22 - Sun, Dec 1
10:41 am - 9:53 pmMDW-SJO
11h 12m1 stop
2:12 pm - 9:46 pmSJO-MDW
7h 34m1 stop
$1,352Delta
Find Deal
Sat, Nov 23 - Sat, Nov 30
3:19 pm - 9:53 pmMDW-SJO
6h 34m1 stop
7:00 am - 5:54 pmSJO-MDW
10h 54m1 stop
$1,503Delta
Find Deal
Fri, Nov 22 - Sun, Dec 1
10:41 am - 9:53 pmMDW-SJO
11h 12m1 stop
7:00 am - 5:02 pmSJO-MDW
10h 02m2 stops
$1,508Delta
Find Deal
Sat, Nov 23 - Sat, Nov 30
6:00 am - 12:45 pmMDW-SJO
6h 45m1 stop
2:12 pm - 9:46 pmSJO-MDW
7h 34m1 stop
$1,517Delta
Find Deal
Sat, Nov 23 - Sat, Nov 30

Southwest flights from Chicago Midway Airport to San José, San José Province

Our best Southwest deals on Chicago Midway Airport to San José, San José Province flight tickets
Southwest
Mar 2
MDW5:35 amChicago Midway
7h 20m
1 stop
SJO12:55 pmSan José Juan Santamaria Intl
Mar 12
SJO8:45 amSan José Juan Santamaria Intl
12h 35m
2 stops
MDW10:20 pmChicago Midway
Southwest
Dec 6
MDW8:40 amChicago Midway
12h 00m
2 stops
SJO8:40 pmSan José Juan Santamaria Intl
Dec 12
SJO1:40 pmSan José Juan Santamaria Intl
19h 00m
2 stops
MDW8:40 amChicago Midway
Southwest
Feb 26
MDW5:45 amChicago Midway
7h 10m
1 stop
SJO12:55 pmSan José Juan Santamaria Intl
Mar 4
SJO9:55 amSan José Juan Santamaria Intl
8h 55m
2 stops
MDW6:50 pmChicago Midway

Delta flights from Chicago Midway Airport to San José, San José Province

Our best Delta deals on Chicago Midway Airport to San José, San José Province flight tickets
Delta
Dec 7
MDW6:00 amChicago Midway
6h 48m
1 stop
SJO12:48 pmSan José Juan Santamaria Intl
Dec 11
SJO7:00 amSan José Juan Santamaria Intl
10h 01m
2 stops
MDW5:01 pmChicago Midway
Delta
Dec 2
MDW3:19 pmChicago Midway
6h 34m
1 stop
SJO9:53 pmSan José Juan Santamaria Intl
Dec 10
SJO7:00 amSan José Juan Santamaria Intl
9h 12m
1 stop
MDW4:12 pmChicago Midway
Delta
Dec 2
MDW9:31 amChicago Midway
12h 22m
2 stops
SJO9:53 pmSan José Juan Santamaria Intl
Dec 10
SJO7:00 amSan José Juan Santamaria Intl
10h 01m
2 stops
MDW5:01 pmChicago Midway

See travel insights to San José from

How to get the cheapest flight ticket from Chicago Midway Airport to San José, San José Province

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago Midway Airport and San José, San José Province?

What is the cheapest month to fly to San José, San José Province?

The month of May is, on average, the cheapest month to fly to San José, San José Province from Chicago Midway Airport, with most prices found around $476. If you’re not able to fly to San José, San José Province in May, then February is your next best option. Flight prices from Chicago Midway Airport to San José, San José Province during February average around $497.

What is the cheapest day to depart on your flight to San José, San José Province?

The cheapest day to depart from Chicago Midway Airport to San José, San José Province is on a Wednesday when prices can be found for as low as $452. The most expensive day to fly to San José, San José Province is Saturday, with ticket prices averaging around $686.

What is the cheapest time of day to depart on your flight to San José, San José Province?

In the evening is the cheapest time of day to fly from Chicago Midway Airport to San José, San José Province when you can find flight prices for as low as $468. Flying to San José, San José Province in the evening is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to San José, San José Province, so prices are often more expensive at around $646 per ticket.

How far in advance should I book a flight to San José, San José Province?

We recommend purchasing flights from Chicago Midway Airport to San José, San José Province 37 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to San José, San José Province for $574. Keep in mind that you might also find cheap flights to San José, San José Province outside of this time window. In fact, momondo users recently found flights from Chicago Midway Airport to San José, San José Province for $307.

Can stopping save me money on Chicago Midway Airport to San José, San José Province flights?

You could potentially save up to 17% on your flight if you consider stops on a Chicago Midway Airport to San José, San José Province flight.

When to book flights from Chicago Midway Airport to San José, San José Province

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José, San José Province according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José, San José Province (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José, San José Province

Best Price Found

$162

Fastest flight time

6h 34m

Direct flights

None

Airports in San José, San José Province

1 airport
The best one-way flight to San José, San José Province from Chicago Midway Airport in the past 72 hours is $162. The best round-trip flight deal from Chicago Midway Airport to San José, San José Province found on momondo in the last 72 hours is $514.
The fastest flight from Chicago Midway Airport to San José, San José Province takes 6h 34m
There are no direct flights from Chicago Midway Airport to San José, San José Province. Popular non-direct route for this connection is Chicago Midway Airport - San José Juan Santamaria Intl Airport.
There is 1 airport near San José, San José Province: San José Juan Santamaria Intl (SJO)

  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 6h 34m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José, San José Province?


Best airlines flying from Chicago Midway Airport to San José, San José Province

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José, San José Province with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $479Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
DeltaPriceFrom $584Free CancellationRating
8.0
8,755 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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