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Cheap flights from San José, San José Province to Chicago Midway Airport from $166

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 3/1. 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.
1:57 am - 7:06 pmSJO-MDW
41h 09m2 stops
4:41 pm - 12:59 amMDW-SJO
32h 18m3 stops
Mon, Feb 3 - Mon, Feb 10
1:57 am - 7:06 pmSJO-MDW
41h 09m2 stops
6:15 am - 12:26 pmMDW-SJO
30h 11m2 stops
Mon, Feb 3 - Mon, Feb 10
1:31 pm - 3:13 pmSJO-MDW
25h 42m1 stop
8:15 am - 12:59 amMDW-SJO
40h 44m3 stops
Wed, Jan 22 - Wed, Jan 29
1:57 am - 4:16 pmSJO-MDW
38h 19m2 stops
7:25 am - 10:17 amMDW-SJO
26h 52m2 stops
Sun, Feb 9 - Sun, Feb 16
11:38 am - 1:24 pmSJO-MDW
25h 46m1 stop
6:25 am - 10:15 amMDW-SJO
27h 50m2 stops
$520Frontier
Find Deal
Sun, Dec 29 - Wed, Jan 1
11:38 am - 1:24 pmSJO-MDW
25h 46m1 stop
8:25 am - 10:18 amMDW-SJO
25h 53m1 stop
$522Frontier
Find Deal
Sun, Dec 29 - Wed, Jan 1
8:45 am - 9:05 pmSJO-MDW
11h 20m2 stops
1:25 pm - 7:40 pmMDW-SJO
7h 15m1 stop
$547Southwest
Find Deal
Tue, Apr 22 - Tue, Apr 29
9:55 am - 7:45 pmSJO-MDW
9h 50m1 stop
8:25 am - 8:40 pmMDW-SJO
12h 15m1 stop
$558Southwest
Find Deal
Wed, Jan 22 - Wed, Jan 29
7:00 am - 5:01 pmSJO-MDW
10h 01m2 stops
12:44 pm - 9:52 pmMDW-SJO
9h 08m1 stop
$639Delta
Find Deal
Sat, Dec 7 - Thu, Feb 27
7:00 am - 5:01 pmSJO-MDW
10h 01m2 stops
10:57 am - 9:52 pmMDW-SJO
10h 55m1 stop
$676Delta
Find Deal
Sat, Dec 7 - Thu, Feb 27
1:00 pm - 10:04 pmSJO-MDW
9h 04m1 stop
$166Frontier
Find Deal
Sat, Mar 1
12:23 pm - 9:55 amSJO-MDW
21h 32m1 stop
Tue, Dec 17
1:29 pm - 8:21 amSJO-MDW
18h 52m1 stop
Thu, Dec 19
1:49 am - 1:36 pmSJO-MDW
11h 47m1 stop
Wed, Dec 18
12:27 pm - 8:45 amSJO-MDW
20h 18m2 stops
$291Volaris
Find Deal
Tue, Nov 26
10:40 am - 8:49 pmSJO-MDW
10h 09m1 stop
$323Frontier
Find Deal
Thu, Mar 6
7:00 am - 5:01 pmSJO-MDW
10h 01m2 stops
$346Delta
Find Deal
Sat, Dec 7
9:55 am - 10:10 pmSJO-MDW
12h 15m2 stops
$355Southwest
Find Deal
Sun, Feb 2
7:00 am - 5:02 pmSJO-MDW
10h 02m2 stops
$512Delta
Find Deal
Tue, Dec 3
9:55 am - 6:50 pmSJO-MDW
8h 55m1 stop
$556Southwest
Find Deal
Fri, Nov 29
7:00 am - 5:02 pmSJO-MDW
10h 02m2 stops
9:31 am - 9:53 pmMDW-SJO
12h 22m2 stops
$639Delta
Find Deal
Mon, Nov 25 - Sat, Nov 30
9:55 am - 7:20 pmSJO-MDW
9h 25m2 stops
7:15 am - 8:40 pmMDW-SJO
13h 25m2 stops
$642Southwest
Find Deal
Mon, Nov 25 - Mon, Dec 9
7:00 am - 2:34 pmSJO-MDW
7h 34m1 stop
10:38 am - 9:57 pmMDW-SJO
11h 19m1 stop
$648Delta
Find Deal
Mon, Nov 25 - Mon, Dec 9
9:55 am - 7:20 pmSJO-MDW
9h 25m2 stops
7:15 am - 8:40 pmMDW-SJO
13h 25m2 stops
$652Southwest
Find Deal
Fri, Nov 22 - Fri, Dec 6
7:00 am - 5:02 pmSJO-MDW
10h 02m2 stops
10:41 am - 9:53 pmMDW-SJO
11h 12m1 stop
$653Delta
Find Deal
Mon, Nov 25 - Sat, Nov 30
7:00 am - 2:34 pmSJO-MDW
7h 34m1 stop
9:31 am - 9:53 pmMDW-SJO
12h 22m2 stops
$676Delta
Find Deal
Mon, Nov 25 - Wed, Dec 4
1:40 pm - 12:50 amSJO-MDW
11h 10m2 stops
8:55 am - 8:40 pmMDW-SJO
11h 45m2 stops
$684Southwest
Find Deal
Sun, Nov 24 - Sun, Dec 1
1:40 pm - 12:50 amSJO-MDW
11h 10m2 stops
8:55 am - 8:40 pmMDW-SJO
11h 45m2 stops
$700Southwest
Find Deal
Sun, Nov 24 - Sun, Dec 1
7:00 am - 5:02 pmSJO-MDW
10h 02m2 stops
12:43 pm - 9:53 pmMDW-SJO
9h 10m1 stop
$723Delta
Find Deal
Tue, Nov 26 - Thu, Dec 5
2:52 pm - 8:45 amSJO-MDW
17h 53m2 stops
7:50 pm - 7:15 amMDW-SJO
35h 25m3 stops
$1,015
Find Deal
Tue, Nov 26 - Tue, Dec 3

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

Our best Frontier deals on San José, San José Province to Chicago Midway Airport flight tickets
Frontier
Dec 29
SJO11:38 amSan José Juan Santamaria Intl
25h 46m
1 stop
MDW1:24 pmChicago Midway
Jan 1
MDW6:25 amChicago Midway
27h 50m
2 stops
SJO10:15 amSan José Juan Santamaria Intl
Frontier
Dec 29
SJO11:38 amSan José Juan Santamaria Intl
25h 46m
1 stop
MDW1:24 pmChicago Midway
Jan 1
MDW8:25 amChicago Midway
25h 53m
1 stop
SJO10:18 amSan José Juan Santamaria Intl
Frontier
Dec 29
SJO11:38 amSan José Juan Santamaria Intl
21h 53m
2 stops
MDW9:31 amChicago Midway
Jan 1
MDW2:30 pmChicago Midway
19h 45m
2 stops
SJO10:15 amSan José Juan Santamaria Intl

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 22
SJO8:45 amSan José Juan Santamaria Intl
11h 20m
2 stops
MDW9:05 pmChicago Midway
Apr 29
MDW1:25 pmChicago Midway
7h 15m
1 stop
SJO7:40 pmSan José Juan Santamaria Intl
Southwest
Jan 22
SJO9:55 amSan José Juan Santamaria Intl
9h 50m
1 stop
MDW7:45 pmChicago Midway
Jan 29
MDW8:25 amChicago Midway
12h 15m
1 stop
SJO8:40 pmSan José Juan Santamaria Intl
Southwest
Apr 16
SJO8:45 amSan José Juan Santamaria Intl
11h 20m
2 stops
MDW9:05 pmChicago Midway
Apr 25
MDW9:45 amChicago Midway
10h 55m
2 stops
SJO7:40 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, Monday is the cheapest day to fly to Chicago Midway Airport from San José, San José Province. The lowest ticket price found for a Monday departure recently was $0. 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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $0 when looking at flights departing in the afternoon. 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 14% 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

$166

Fastest flight time

7h 34m

Direct flights

None
The best one-way flight to Chicago Midway Airport from San José, San José Province in the past 72 hours is $166. 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 $350.
The fastest flight from San José, San José Province to Chicago Midway Airport takes 7h 34m
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 34m 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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