Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from San José, San José Province to Chicago from $147

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 2/2. 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.

"This year, momondo is the #1 place for airfares on the internet."
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.

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.
2:52 pm - 5:37 amSJO-ORD
13h 45m1 stop
1:48 am - 1:57 pmORD-SJO
13h 09m1 stop
Tue, Mar 18 - Mon, Mar 24
2:52 pm - 5:44 amSJO-ORD
13h 52m1 stop
12:45 pm - 11:15 pmORD-SJO
11h 30m1 stop
$281Volaris
Find Deal
Wed, Apr 23 - Tue, Apr 29
1:49 am - 10:32 amSJO-ORD
8h 43m1 stop
5:05 am - 12:33 pmORD-SJO
7h 28m1 stop
$305Spirit Airlines
Find Deal
Sun, Dec 15 - Thu, Feb 20
1:49 am - 4:06 pmSJO-ORD
14h 17m1 stop
5:11 pm - 12:54 amORD-SJO
7h 43m1 stop
$309Spirit Airlines
Find Deal
Sun, Dec 22 - Tue, Dec 31
2:15 am - 1:15 pmSJO-ORD
10h 00m1 stop
3:05 pm - 12:15 amORD-SJO
10h 10m1 stop
$423Avianca
Find Deal
Mon, Mar 10 - Tue, Mar 25
4:55 pm - 12:15 pmSJO-ORD
19h 20m1 stop
2:35 pm - 11:20 pmORD-SJO
8h 45m2 stops
$454Avianca
Find Deal
Tue, Dec 3 - Fri, Dec 6
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
2:53 pm - 4:37 amSJO-ORD
13h 44m1 stop
Sun, Feb 2
2:53 pm - 4:37 amSJO-ORD
13h 44m1 stop
Mon, Mar 3
1:49 am - 9:37 amSJO-ORD
7h 48m1 stop
$151Spirit Airlines
Find Deal
Mon, Dec 16
12:23 pm - 10:59 pmSJO-ORD
10h 36m1 stop
$158Spirit Airlines
Find Deal
Tue, Dec 17
3:10 pm - 1:15 pmSJO-ORD
22h 05m2 stops
$165Avianca
Find Deal
Tue, Dec 24
9:35 am - 1:15 pmSJO-ORD
27h 40m2 stops
$174Avianca
Find Deal
Tue, Dec 24
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$341United Airlines
Find Deal
Sat, Dec 7
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$351United Airlines
Find Deal
Sat, Dec 21
6:30 am - 8:36 pmSJO-ORD
14h 06m2 stops
$395American Airlines
Find Deal
Fri, Mar 7
6:30 am - 11:49 pmSJO-ORD
17h 19m1 stop
$398American Airlines
Find Deal
Fri, Nov 29
2:52 pm - 4:37 amSJO-ORD
13h 45m1 stop
8:27 pm - 12:19 pmORD-SJO
15h 52m1 stop
Mon, Nov 25 - Tue, Dec 3
2:52 pm - 4:37 amSJO-ORD
13h 45m1 stop
5:11 pm - 12:53 amORD-SJO
7h 42m1 stop
Mon, Nov 25 - Sat, Dec 7
1:56 am - 2:31 pmSJO-ORD
12h 35m1 stop
5:41 pm - 1:01 amORD-SJO
7h 20m1 stop
$404Spirit Airlines
Find Deal
Mon, Nov 25 - Mon, Dec 2
1:56 am - 2:31 pmSJO-ORD
12h 35m1 stop
1:09 pm - 1:01 amORD-SJO
11h 52m2 stops
$427Spirit Airlines
Find Deal
Mon, Nov 25 - Tue, Dec 3
2:15 am - 12:15 pmSJO-ORD
10h 00m1 stop
2:35 pm - 10:55 pmORD-SJO
8h 20m1 stop
$453Avianca
Find Deal
Sun, Nov 24 - Wed, Dec 4
2:15 am - 12:15 pmSJO-ORD
10h 00m1 stop
2:35 pm - 11:20 pmORD-SJO
8h 45m2 stops
$454Avianca
Find Deal
Tue, Nov 26 - Wed, Dec 4
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
$633United Airlines
Find Deal
Sun, Nov 24 - Sat, Nov 30
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
9:32 pm - 1:17 pmORD-SJO
15h 45m1 stop
$638United Airlines
Find Deal
Sun, Nov 24 - Mon, Dec 9
1:15 pm - 10:14 pmSJO-ORD
8h 59m1 stop
10:15 am - 10:59 pmORD-SJO
12h 44m1 stop
$648American Airlines
Find Deal
Fri, Nov 22 - Mon, Dec 2
7:00 am - 7:08 pmSJO-ORD
12h 08m2 stops
1:15 pm - 11:20 pmORD-SJO
10h 05m2 stops
$666American Airlines
Find Deal
Sat, Nov 23 - Sat, Dec 7
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
$633United Airlines
Find Deal
Sun, Jan 26 - Sun, Feb 2
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
$654United Airlines
Find Deal
Sun, Jan 12 - Sun, Feb 16
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
$670United Airlines
Find Deal
Sun, Dec 8 - Sun, Dec 15
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
2:35 pm - 9:45 pmORD-SJO
7h 10mnonstop
$713Avianca
Find Deal
Wed, Jan 22 - Wed, Jan 29
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
2:35 pm - 9:45 pmORD-SJO
7h 10mnonstop
$772Avianca
Find Deal
Sun, Dec 8 - Fri, Dec 13
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
$788United Airlines
Find Deal
Sat, Dec 21 - Sat, Jan 4
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
2:35 pm - 9:45 pmORD-SJO
7h 10mnonstop
$808Avianca
Find Deal
Sun, Dec 8 - Sun, Dec 15
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
2:35 pm - 9:45 pmORD-SJO
7h 10mnonstop
$853Avianca
Find Deal
Fri, Dec 20 - Fri, Jan 3
5:45 am - 1:15 pmSJO-ORD
7h 30mnonstop
2:35 pm - 9:45 pmORD-SJO
7h 10mnonstop
$858Avianca
Find Deal
Wed, Dec 25 - Wed, Jan 1
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
$870United Airlines
Find Deal
Sat, Dec 21 - Sat, Jan 4

Volaris flights from San José, San José Province to Chicago

Our best Volaris deals on San José, San José Province to Chicago flight tickets
Volaris
Apr 23
SJO2:52 pmSan José Juan Santamaria Intl
13h 52m
1 stop
ORD5:44 amChicago O'Hare Intl
Apr 29
ORD12:45 pmChicago O'Hare Intl
11h 30m
1 stop
SJO11:15 pmSan José Juan Santamaria Intl
Volaris
Mar 18
SJO2:52 pmSan José Juan Santamaria Intl
13h 45m
1 stop
ORD5:37 amChicago O'Hare Intl
Mar 24
ORD1:48 amChicago O'Hare Intl
13h 09m
1 stop
SJO1:57 pmSan José Juan Santamaria Intl
Volaris
Mar 18
SJO2:52 pmSan José Juan Santamaria Intl
13h 45m
1 stop
ORD5:37 amChicago O'Hare Intl
Mar 25
ORD12:45 pmChicago O'Hare Intl
11h 30m
1 stop
SJO11:15 pmSan José Juan Santamaria Intl

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
Dec 15
SJO1:49 amSan José Juan Santamaria Intl
8h 43m
1 stop
ORD10:32 amChicago O'Hare Intl
Feb 20
ORD5:05 amChicago O'Hare Intl
7h 28m
1 stop
SJO12:33 pmSan José Juan Santamaria Intl
Spirit Airlines
Dec 22
SJO1:49 amSan José Juan Santamaria Intl
14h 17m
1 stop
ORD4:06 pmChicago O'Hare Intl
Dec 31
ORD5:11 pmChicago O'Hare Intl
7h 43m
1 stop
SJO12:54 amSan José Juan Santamaria Intl
Spirit Airlines
Jan 20
SJO1:57 amSan José Juan Santamaria Intl
18h 16m
1 stop
ORD8:13 pmChicago O'Hare Intl
Jan 27
ORD6:06 pmChicago O'Hare Intl
17h 12m
1 stop
SJO11:18 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

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 month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from San José, San José Province, with most prices found around $348. If you’re not able to fly to Chicago in February, then August is your next best option. Flight prices from San José, San José Province to Chicago during August average around $357.

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 Tuesday when prices can be found for as low as $333. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, 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 $581.

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 $368. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $549.

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?

The best time to book a flight to Chicago from San José, San José Province is 43 days out, which is when prices tend to be around $426. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $272.

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.

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

You could potentially save up to 56% on your flight if you consider stops on a San José, San José Province to Chicago flight.

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

As of November 2024, prices for San José, San José Province to Chicago flights are approximately 4% more expensive 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

$147

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 $147. The best round-trip flight deal from San José, San José Province to Chicago found on momondo in the last 72 hours is $279.
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 34m, 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
8,169 reviews
Search Spirit Airlines flights
AviancaPriceFrom $262Free CancellationRating
7.0
2,794 reviews
Search Avianca flights
Copa AirlinesPriceFrom $393Free CancellationRating
7.7
1,779 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $484Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $521Free CancellationRating
8.0
8,755 reviews
Search Delta flights
United AirlinesPriceFrom $567Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights

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?
Tue 11/26
Tue 12/3
Email me momondo's favorite deals

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