Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from San José, San José Province to Chicago from $131

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 departing on 3/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

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.
12:50 am - 2:21 pmSJO-ORD
12h 31m2 stops
4:15 pm - 11:50 pmORD-SJO
8h 35m1 stop
$234Spirit Airlines
Find Deal
ter, mar 18 - ter, abr 1
12:26 pm - 9:44 amSJO-ORD
20h 18m2 stops
3:16 pm - 11:21 amORD-SJO
21h 05m2 stops
$248Spirit Airlines
Find Deal
ter, mar 18 - qua, mar 26
12:50 am - 12:59 amSJO-ORD
23h 09m2 stops
9:08 pm - 10:25 amORD-SJO
14h 17m1 stop
$250Spirit Airlines
Find Deal
seg, mar 17 - qua, mar 26
12:50 am - 3:46 pmSJO-MDW
13h 56m2 stops
4:40 pm - 10:50 amMDW-SJO
19h 10m1 stop
ter, mar 18 - ter, abr 1
2:43 pm - 5:37 amSJO-ORD
13h 54m1 stop
12:14 pm - 11:50 pmORD-SJO
12h 36m2 stops
seg, mar 10 - qua, mar 26
5:51 am - 11:27 pmSJO-ORD
17h 36m1 stop
7:55 am - 7:07 pmORD-SJO
12h 12m1 stop
$437Copa Airlines
Find Deal
ter, mar 4 - dom, mar 9
7:00 am - 6:02 pmSJO-MDW
10h 02m2 stops
12:51 pm - 9:24 pmMDW-SJO
9h 33m1 stop
$440Delta
Find Deal
ter, mar 18 - qua, mar 26
1:10 pm - 10:50 pmSJO-MDW
8h 40m1 stop
5:55 am - 12:10 pmMDW-SJO
7h 15m1 stop
$486Southwest
Find Deal
qua, abr 30 - ter, mai 6
1:40 pm - 12:05 amSJO-MDW
9h 25m1 stop
8:30 am - 7:05 pmMDW-SJO
11h 35m1 stop
$489Southwest
Find Deal
seg, ago 18 - dom, ago 24
7:00 am - 4:14 pmSJO-MDW
8h 14m1 stop
12:51 pm - 9:24 pmMDW-SJO
9h 33m1 stop
$524Delta
Find Deal
ter, mar 18 - qua, mar 26

Spirit Airlines flights from San José, San José Province to Chicago

Our best Spirit Airlines deals on San José, San José Province to Chicago flight tickets
Spirit Airlines
Mar 18
SJO12:50 amSan José Juan Santamaria Intl
12h 31m
2 stops
ORD2:21 pmChicago O'Hare Intl
Apr 1
ORD4:15 pmChicago O'Hare Intl
8h 35m
1 stop
SJO11:50 pmSan José Juan Santamaria Intl
Spirit Airlines
Mar 18
SJO12:26 pmSan José Juan Santamaria Intl
20h 18m
2 stops
ORD9:44 amChicago O'Hare Intl
Mar 26
ORD3:16 pmChicago O'Hare Intl
21h 05m
2 stops
SJO11:21 amSan José Juan Santamaria Intl
Spirit Airlines
Mar 17
SJO12:50 amSan José Juan Santamaria Intl
23h 09m
2 stops
ORD12:59 amChicago O'Hare Intl
Mar 26
ORD9:08 pmChicago O'Hare Intl
14h 17m
1 stop
SJO10:25 amSan José Juan Santamaria Intl

Copa Airlines flights from San José, San José Province to Chicago

Our best Copa Airlines deals on San José, San José Province to Chicago flight tickets
Copa Airlines
Mar 4
SJO5:51 amSan José Juan Santamaria Intl
17h 36m
1 stop
ORD11:27 pmChicago O'Hare Intl
Mar 9
ORD7:55 amChicago O'Hare Intl
12h 12m
1 stop
SJO7:07 pmSan José Juan Santamaria Intl
Copa Airlines
Mar 3
SJO4:09 amSan José Juan Santamaria Intl
8h 33m
1 stop
ORD12:42 pmChicago O'Hare Intl
Mar 7
ORD6:55 amChicago O'Hare Intl
11h 56m
1 stop
SJO6:51 pmSan José Juan Santamaria Intl
Copa Airlines
Mar 1
SJO4:09 amSan José Juan Santamaria Intl
19h 18m
1 stop
ORD11:27 pmChicago O'Hare Intl
Mar 9
ORD7:55 amChicago O'Hare Intl
9h 00m
1 stop
SJO3:55 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

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 San José, San José Province and Chicago?

What is the cheapest month to fly to Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from San José, San José Province, with most prices found around $366. If you’re not able to fly to Chicago in August, then May is your next best option. Flight prices from San José, San José Province to Chicago during May average around $399.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $330. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from San José, San José Province to Chicago for around $655.

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

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from San José, San José Province to Chicago during this time can be as low as $335. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $619.

What is the cheapest San José Juan Santamaria Intl to Chicago flight route?

Fly from San José Juan Santamaria Intl to Chicago O'Hare Intl for the best San José Juan Santamaria Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from San José, San José Province when booking 3 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $476 when searching 3 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from San José, San José Province for as low as $368 on momondo.

What cabin class options are available on San José Juan Santamaria Intl to Chicago flights?

There are 3 cabin classes available to choose from on San José Juan Santamaria Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have San José, San José Province to Chicago flight prices changed over time?

As of February 2025, prices for San José, San José Province to Chicago flights are approximately 28% cheaper when compared to flights at the same time last year.

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

Are you open to changing your travel dates? Check out the ideal times to fly from San José, San José Province to Chicago 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 (SJO to CHI) flight deals and tips

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

Best Price Found

$131

Fastest flight time

5h 25m

Direct flights

Mon, Thu, Sat and Sun

Airports in Chicago

2 airports
The best one-way flight to Chicago from San José, San José Province in the past 72 hours is $131. The best round-trip flight deal from San José, San José Province to Chicago found on momondo in the last 72 hours is $234.
The fastest flight from San José, San José Province to Chicago takes 5h 25m
Direct flights go from San José, San José Province to Chicago on Monday, Thursday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and Avianca.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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

    A flight from San José Juan Santamaria Intl to Chicago will travel around 2215.9 mi. Flights usually cover this in 7h 55m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from San José Juan Santamaria Intl Airport to Chicago are refreshed on a daily basis.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from San José Juan Santamaria Intl Airport to Chicago.

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

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from San José, San José Province to Chicago?

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


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

Compare and see reviews for airlines that fly from San José, San José Province to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $205Free CancellationRating
6.3
8,012 reviews
Search Spirit Airlines flights
Copa AirlinesPriceFrom $320Free CancellationRating
7.6
1,502 reviews
Search Copa Airlines flights
AviancaPriceFrom $371Free CancellationRating
6.8
2,431 reviews
Search Avianca flights
American AirlinesPriceFrom $484Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $521Free CancellationRating
8.0
8,212 reviews
Search Delta flights
United AirlinesPriceFrom $557Free CancellationRating
7.4
8,759 reviews
Search United Airlines flights
  • United Airlines Flights From San José, San José Province to Chicago

    The lowest priced United Airlines flight from San José, San José Province to Chicago from the last 72 hours was $557. Generally, United Airlines has 2 flights on this route every week with an average price of $664. United Airlines is rated 7.4/10 by our users.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from San José to Chicago for you.

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

Yes. momondo allows you to filter the results for San José to Chicago flights to just show those with flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from San José.

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.


An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
qui 2/27
qui 3/6

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago