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Cheap flights from San José, San José Province to Chicago Midway Airport from $208

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San José, San José Province to Chicago Midway Airport departing on 5/10. 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 San José, San José Province to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from San José, San José Province to Chicago.
1:10 pm - 11:35 pmSJO-MDW
9h 25m1 stop
5:55 am - 12:10 pmMDW-SJO
7h 15m1 stop
$444Southwest
Find Deal
Thu, Apr 24 - Sun, Apr 27
1:40 pm - 12:05 amSJO-MDW
9h 25m1 stop
10:10 am - 6:55 pmMDW-SJO
9h 45m1 stop
$447Southwest
Find Deal
Fri, Aug 15 - Sat, Aug 23
1:40 pm - 12:05 amSJO-MDW
9h 25m1 stop
8:00 am - 6:55 pmMDW-SJO
11h 55m2 stops
$451Southwest
Find Deal
Fri, Aug 15 - Sat, Aug 23
12:28 pm - 7:46 pmSJO-MDW
30h 18m2 stops
10:31 am - 3:13 pmMDW-SJO
29h 42m2 stops
Thu, Jun 12 - Mon, Jul 14
12:23 pm - 12:10 pmSJO-MDW
22h 47m2 stops
12:46 pm - 10:24 amMDW-SJO
22h 38m1 stop
Thu, Apr 10 - Sun, Apr 13
1:10 pm - 11:35 pmSJO-MDW
9h 25m1 stop
10:25 am - 7:40 pmMDW-SJO
10h 15m2 stops
$467Southwest
Find Deal
Fri, Apr 25 - Wed, Apr 30
1:47 pm - 11:22 pmSJO-MDW
8h 35m1 stop
6:00 am - 12:37 pmMDW-SJO
7h 37m1 stop
$489Frontier
Find Deal
Sat, Jun 14 - Sat, Jun 21
1:47 pm - 11:22 pmSJO-MDW
8h 35m1 stop
6:00 am - 12:35 pmMDW-SJO
7h 35m1 stop
$517Frontier
Find Deal
Sat, Jun 28 - Sat, Jul 5
1:18 pm - 9:44 pmSJO-MDW
7h 26m1 stop
6:00 am - 11:53 amMDW-SJO
6h 53m1 stop
$518Delta
Find Deal
Mon, Sep 15 - Fri, Sep 19
1:18 pm - 9:44 pmSJO-MDW
7h 26m1 stop
6:00 am - 11:53 amMDW-SJO
6h 53m1 stop
$627Delta
Find Deal
Thu, Sep 25 - Thu, Oct 2

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

Our best Southwest deals on San José, San José Province to Chicago Midway Airport flight tickets
Southwest
Apr 24
SJO1:10 pmSan José Juan Santamaria Intl
9h 25m
1 stop
MDW11:35 pmChicago Midway
Apr 27
MDW5:55 amChicago Midway
7h 15m
1 stop
SJO12:10 pmSan José Juan Santamaria Intl
Southwest
Aug 15
SJO1:40 pmSan José Juan Santamaria Intl
9h 25m
1 stop
MDW12:05 amChicago Midway
Aug 23
MDW10:10 amChicago Midway
9h 45m
1 stop
SJO6:55 pmSan José Juan Santamaria Intl
Southwest
Aug 15
SJO1:40 pmSan José Juan Santamaria Intl
9h 25m
1 stop
MDW12:05 amChicago Midway
Aug 23
MDW8:00 amChicago Midway
11h 55m
2 stops
SJO6:55 pmSan José Juan Santamaria Intl

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

Our best Delta deals on San José, San José Province to Chicago Midway Airport flight tickets
Delta
Apr 3
SJO7:00 amSan José Juan Santamaria Intl
10h 02m
2 stops
MDW6:02 pmChicago Midway
Apr 6
MDW9:23 amChicago Midway
13h 03m
2 stops
SJO9:26 pmSan José Juan Santamaria Intl
Delta
Apr 3
SJO7:00 amSan José Juan Santamaria Intl
10h 02m
2 stops
MDW6:02 pmChicago Midway
Apr 6
MDW9:23 amChicago Midway
13h 03m
2 stops
SJO9:26 pmSan José Juan Santamaria Intl
Delta
Sep 15
SJO1:18 pmSan José Juan Santamaria Intl
7h 26m
1 stop
MDW9:44 pmChicago Midway
Sep 19
MDW6:00 amChicago Midway
6h 53m
1 stop
SJO11:53 amSan José Juan Santamaria Intl

See travel insights to Chicago from

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

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 cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from San José, San José Province. The lowest ticket price found for a Thursday departure recently was $599. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from San José, San José Province because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $976.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from San José, San José Province in the morning is the least expensive time of day to depart. momondo users have found prices as low as $610 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $896. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

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

Best Price Found

$208

Fastest flight time

7h 26m

Direct flights

None
The best one-way flight to Chicago Midway Airport from San José, San José Province in the past 72 hours is $208. The best round-trip flight deal from San José, San José Province to Chicago Midway Airport found on momondo in the last 72 hours is $444.
The fastest flight from San José, San José Province to Chicago Midway Airport takes 7h 26m
There are no direct flights from San José, San José Province to Chicago Midway Airport. Popular non-direct route for this connection is San José Juan Santamaria Intl Airport - Chicago Midway Airport.

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

    San José Juan Santamaria Intl and Chicago Midway are 2210.5 mi apart from one another. Typically, this will take 7h 26m by plane in normal conditions.

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San José Juan Santamaria Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway 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 Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.


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Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San José to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from San José to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San José to Chicago.

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

Price alerts on flights to Chicago from San José are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


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