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Cheap flights from San José, San José Province to Chicago Midway Airport from $253

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 3/12. 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

These are some of the best round-trip flight deals from San José, San José Province to Chicago 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 San José, San José Province to Chicago.

Cheap last minute flights

Planning a quick getaway from San José, San José Province to Chicago? 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 Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from San José, San José Province to Chicago

Find recent round-trip train or bus tickets from San José, San José Province to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
12:55 pm - 10:04 pmSJO-MDW
9h 09m1 stop
6:48 pm - 11:31 amMDW-SJO
16h 43m1 stop
$372Frontier
Find Deal
Sat, Feb 22 - Fri, Feb 28
12:55 pm - 10:04 pmSJO-MDW
9h 09m1 stop
6:38 pm - 1:05 pmMDW-SJO
18h 27m1 stop
$388Frontier
Find Deal
Sat, Mar 1 - Fri, Mar 7
1:57 am - 2:58 pmSJO-MDW
13h 01m2 stops
10:58 am - 11:18 amMDW-SJO
24h 20m1 stop
Sun, Jan 12 - Sun, Jan 19
8:45 am - 6:35 pmSJO-MDW
8h 50m1 stop
5:50 am - 12:10 pmMDW-SJO
7h 20m1 stop
$569Southwest
Find Deal
Thu, May 1 - Mon, May 5
1:57 am - 7:06 pmSJO-MDW
41h 09m2 stops
4:08 pm - 12:26 pmMDW-SJO
20h 18m2 stops
Mon, Feb 3 - Mon, Feb 10
8:45 am - 10:00 pmSJO-MDW
12h 15m2 stops
7:50 am - 7:40 pmMDW-SJO
12h 50m2 stops
$573Southwest
Find Deal
Thu, May 1 - Mon, May 5
1:10 pm - 10:50 pmSJO-MDW
8h 40m1 stop
7:50 am - 7:40 pmMDW-SJO
12h 50m2 stops
$580Southwest
Find Deal
Wed, Apr 30 - Mon, May 5
8:45 am - 7:35 pmSJO-MDW
9h 50m2 stops
8:05 am - 7:40 pmMDW-SJO
12h 35m2 stops
$584Southwest
Find Deal
Wed, Apr 30 - Mon, May 5
2:19 pm - 10:20 pmSJO-MDW
8h 01m1 stop
6:00 am - 12:54 pmMDW-SJO
6h 54m1 stop
$708Delta
Find Deal
Wed, Feb 19 - Tue, Feb 25
2:19 pm - 10:20 pmSJO-MDW
8h 01m1 stop
10:57 am - 10:12 pmMDW-SJO
11h 15m1 stop
$739Delta
Find Deal
Mon, Jan 13 - Mon, Jan 20
1:41 pm - 7:35 pmSJO-MDW
28h 54m1 stop
Wed, Mar 12
3:06 pm - 3:13 pmSJO-MDW
23h 07m2 stops
Wed, Mar 12
5:52 am - 7:29 pmSJO-MDW
12h 37m2 stops
Thu, Apr 17
1:04 am - 5:49 pmSJO-MDW
15h 45m2 stops
Mon, Apr 28
1:10 pm - 11:35 pmSJO-MDW
9h 25m1 stop
$335Southwest
Find Deal
Thu, Apr 17
8:45 am - 7:35 pmSJO-MDW
9h 50m2 stops
$340Southwest
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Tue, Apr 29
2:15 pm - 10:06 pmSJO-MDW
7h 51m1 stop
$351Delta
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Sat, Dec 28
1:25 pm - 1:02 pmSJO-MDW
22h 37m1 stop
$355Frontier
Find Deal
Sat, Mar 15
11:38 am - 1:24 pmSJO-MDW
25h 46m1 stop
$386Frontier
Find Deal
Sun, Dec 29
2:15 pm - 10:06 pmSJO-MDW
7h 51m1 stop
$419Delta
Find Deal
Sun, Dec 29
2:15 pm - 10:06 pmSJO-MDW
7h 51m1 stop
9:34 am - 10:12 pmMDW-SJO
12h 38m2 stops
$639Delta
Find Deal
Sat, Dec 28 - Wed, Jan 8
2:15 pm - 10:06 pmSJO-MDW
7h 51m1 stop
9:30 am - 9:55 pmMDW-SJO
12h 25m2 stops
$660Delta
Find Deal
Sat, Dec 28 - Sun, Jan 5
2:15 pm - 10:06 pmSJO-MDW
7h 51m1 stop
10:57 am - 10:12 pmMDW-SJO
11h 15m1 stop
$708Delta
Find Deal
Sat, Dec 28 - Wed, Jan 8
11:38 am - 1:24 pmSJO-MDW
25h 46m1 stop
6:49 pm - 11:41 amMDW-SJO
16h 52m1 stop
Thu, Dec 26 - Mon, Dec 30
2:15 pm - 10:06 pmSJO-MDW
7h 51m1 stop
9:34 am - 10:12 pmMDW-SJO
12h 38m2 stops
$739Delta
Find Deal
Sat, Dec 28 - Mon, Jan 6
11:38 am - 1:24 pmSJO-MDW
25h 46m1 stop
9:59 pm - 11:41 amMDW-SJO
13h 42m2 stops
Thu, Dec 26 - Mon, Dec 30
1:08 pm - 8:45 amSJO-MDW
19h 37m2 stops
6:49 pm - 11:41 amMDW-SJO
16h 52m1 stop
Fri, Dec 27 - Mon, Dec 30
9:55 am - 8:35 pmSJO-MDW
10h 40m2 stops
7:35 am - 8:40 pmMDW-SJO
13h 05m2 stops
$884Southwest
Find Deal
Fri, Dec 27 - Sat, Jan 4
9:55 am - 6:50 pmSJO-MDW
8h 55m1 stop
5:05 am - 12:15 pmMDW-SJO
7h 10m1 stop
$906Southwest
Find Deal
Tue, Dec 24 - Sat, Dec 28
9:55 am - 10:20 pmSJO-MDW
12h 25m2 stops
7:35 am - 8:40 pmMDW-SJO
13h 05m2 stops
$911Southwest
Find Deal
Tue, Dec 24 - Sat, Dec 28

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
May 1
SJO8:45 amSan José Juan Santamaria Intl
8h 50m
1 stop
MDW6:35 pmChicago Midway
May 5
MDW5:50 amChicago Midway
7h 20m
1 stop
SJO12:10 pmSan José Juan Santamaria Intl
Southwest
May 1
SJO8:45 amSan José Juan Santamaria Intl
12h 15m
2 stops
MDW10:00 pmChicago Midway
May 5
MDW7:50 amChicago Midway
12h 50m
2 stops
SJO7:40 pmSan José Juan Santamaria Intl
Southwest
Apr 30
SJO1:10 pmSan José Juan Santamaria Intl
8h 40m
1 stop
MDW10:50 pmChicago Midway
May 5
MDW7:50 amChicago Midway
12h 50m
2 stops
SJO7:40 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
Dec 28
SJO2:15 pmSan José Juan Santamaria Intl
7h 51m
1 stop
MDW10:06 pmChicago Midway
Jan 8
MDW9:34 amChicago Midway
12h 38m
2 stops
SJO10:12 pmSan José Juan Santamaria Intl
Delta
Dec 28
SJO2:15 pmSan José Juan Santamaria Intl
7h 51m
1 stop
MDW10:06 pmChicago Midway
Jan 5
MDW9:30 amChicago Midway
12h 25m
2 stops
SJO9:55 pmSan José Juan Santamaria Intl
Delta
Feb 19
SJO2:19 pmSan José Juan Santamaria Intl
8h 01m
1 stop
MDW10:20 pmChicago Midway
Feb 25
MDW6:00 amChicago Midway
6h 54m
1 stop
SJO12:54 pmSan 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.

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

You could potentially save up to 12% on your flight if you consider stops on a San José, San José Province to Chicago Midway Airport flight.

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

$253

Fastest flight time

7h 35m

Direct flights

None
The best one-way flight to Chicago Midway Airport from San José, San José Province in the past 72 hours is $253. 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 $372.
The fastest flight from San José, San José Province to Chicago Midway Airport takes 7h 35m
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 35m 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.


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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