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Cheap flights from San José, San José Province to Chicago from $156

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 2/5. 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 from San José, San José Province to Chicago

The cheapest plane tickets from San José, San José Province to Chicago found on KAYAK recently.
1:25 pm - 11:58 pmSJO-ORD
10h 33m1 stop
5:00 am - 12:20 pmORD-SJO
7h 20m1 stop
$287Spirit Airlines
Find Deal
Thu, Feb 20 - Wed, Feb 26
1:25 pm - 11:58 pmSJO-ORD
10h 33m1 stop
5:00 am - 12:20 pmORD-SJO
7h 20m1 stop
$290Spirit Airlines
Find Deal
Tue, Feb 25 - Tue, Mar 4
4:00 am - 1:02 amSJO-ORD
21h 02m1 stop
5:00 am - 12:20 pmORD-SJO
7h 20m1 stop
Wed, Feb 19 - Wed, Feb 26
8:25 am - 9:30 pmSJO-ORD
12h 05m1 stop
7:00 am - 10:40 pmORD-SJO
16h 40m1 stop
Thu, May 8 - Tue, May 13
2:15 am - 12:15 pmSJO-ORD
10h 00m1 stop
1:35 pm - 9:20 amORD-SJO
19h 45m1 stop
$433Avianca
Find Deal
Wed, Jan 29 - Mon, Feb 3
1:55 am - 1:15 pmSJO-ORD
10h 20m1 stop
2:35 pm - 11:30 pmORD-SJO
9h 55m1 stop
$445Avianca
Find Deal
Fri, Jun 6 - Fri, Jun 13
1:55 pm - 11:40 pmSJO-MDW
8h 45m1 stop
10:00 am - 7:40 pmMDW-SJO
10h 40m2 stops
$544Southwest
Find Deal
Tue, Mar 11 - Tue, Apr 8
8:45 am - 6:35 pmSJO-MDW
8h 50m1 stop
10:25 am - 7:40 pmMDW-SJO
10h 15m2 stops
$560Southwest
Find Deal
Thu, May 1 - Tue, May 6
7:00 am - 6:11 pmSJO-MDW
11h 11m2 stops
10:57 am - 10:12 pmMDW-SJO
11h 15m1 stop
$651Delta
Find Deal
Mon, Feb 3 - Mon, Feb 17
7:00 am - 4:14 pmSJO-MDW
8h 14m1 stop
9:25 am - 9:24 pmMDW-SJO
12h 59m2 stops
$720Delta
Find Deal
Tue, Mar 11 - Tue, Mar 25
1:57 am - 11:34 pmSJO-ORD
21h 37m2 stops
$156Spirit Airlines
Find Deal
Wed, Feb 5
1:57 am - 8:13 pmSJO-ORD
18h 16m1 stop
$163Spirit Airlines
Find Deal
Wed, Feb 5
1:40 am - 1:15 pmSJO-ORD
10h 35m1 stop
$240Avianca
Find Deal
Thu, May 29
2:15 am - 12:15 pmSJO-ORD
10h 00m1 stop
$253Avianca
Find Deal
Sat, Feb 8
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
$347United Airlines
Find Deal
Sun, Feb 9
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
$356United Airlines
Find Deal
Sat, May 24
6:05 am - 5:40 pmSJO-ORD
10h 35m2 stops
$361American Airlines
Find Deal
Tue, Apr 15
7:10 am - 7:33 pmSJO-ORD
11h 23m2 stops
$370American Airlines
Find Deal
Sat, May 24
4:09 am - 11:27 pmSJO-ORD
19h 18m1 stop
$435Copa Airlines
Find Deal
Sat, Feb 15
3:06 pm - 11:27 pmSJO-ORD
8h 21m1 stop
$590Copa Airlines
Find Deal
Mon, Feb 3
1:57 am - 8:13 pmSJO-ORD
18h 16m1 stop
10:25 am - 11:50 pmORD-SJO
14h 25m1 stop
$425Spirit Airlines
Find Deal
Tue, Jan 21 - Tue, Apr 1
8:55 am - 7:42 pmSJO-ORD
10h 47m1 stop
6:06 pm - 11:18 amORD-SJO
17h 12m1 stop
Sun, Jan 19 - Sun, Jan 26
6:15 am - 6:50 pmSJO-ORD
12h 35m1 stop
6:06 pm - 11:18 amORD-SJO
17h 12m1 stop
Sat, Jan 18 - Sun, Jan 26
4:55 pm - 12:15 pmSJO-ORD
19h 20m1 stop
2:05 pm - 12:15 amORD-SJO
10h 10m1 stop
$471Avianca
Find Deal
Tue, Jan 21 - Tue, Mar 4
4:55 pm - 12:15 pmSJO-ORD
19h 20m1 stop
2:05 pm - 9:20 amORD-SJO
19h 15m1 stop
$472Avianca
Find Deal
Tue, Jan 21 - Thu, Jan 30
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
7:35 am - 8:39 pmORD-SJO
13h 04m1 stop
$645United Airlines
Find Deal
Sat, Jan 18 - Mon, Jan 20
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
7:10 am - 10:00 pmORD-SJO
14h 50m1 stop
$650United Airlines
Find Deal
Sat, Jan 18 - Fri, Jan 24
9:55 am - 6:50 pmSJO-MDW
8h 55m2 stops
10:00 am - 8:40 pmMDW-SJO
10h 40m2 stops
$771Southwest
Find Deal
Tue, Jan 21 - Sun, Jan 26
9:55 am - 9:25 pmSJO-MDW
11h 30m2 stops
10:25 am - 8:40 pmMDW-SJO
10h 15m2 stops
$775Southwest
Find Deal
Sun, Jan 19 - Tue, Jan 21
7:00 am - 9:15 pmSJO-ORD
14h 15m2 stops
5:45 am - 12:54 pmORD-SJO
7h 09m1 stop
$799Delta
Find Deal
Sat, Jan 18 - Fri, Jan 24
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
$645United Airlines
Find Deal
Sun, May 25 - Sat, May 31
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
7:35 am - 11:56 amORD-SJO
5h 21mnonstop
$666United Airlines
Find Deal
Sun, Feb 2 - Sun, Mar 9
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
$710United Airlines
Find Deal
Sun, Jun 8 - Sun, Jul 13
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
$730United Airlines
Find Deal
Sun, Jun 15 - Sun, Jul 13
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
$846United Airlines
Find Deal
Sat, Jun 7 - Sun, Jul 13
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
$875United Airlines
Find Deal
Sun, Jun 8 - Sat, Jul 12
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
$896United Airlines
Find Deal
Sun, Jun 15 - Sat, Jul 12
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
$975United Airlines
Find Deal
Sat, Jun 7 - Sat, Jul 12
1:00 pm - 7:34 pmSJO-ORD
5h 34mnonstop
7:41 am - 11:55 amORD-SJO
5h 14mnonstop
$1,010United Airlines
Find Deal
Sat, Jun 14 - Sat, Jul 12
2:05 pm - 7:30 pmSJO-ORD
5h 25mnonstop
7:35 am - 12:56 pmORD-SJO
5h 21mnonstop
$1,048United Airlines
Find Deal
Sat, Feb 15 - Sat, Feb 22

Avianca flights from San José, San José Province to Chicago

Our best Avianca deals on San José, San José Province to Chicago flight tickets
Avianca
Jan 29
SJO2:15 amSan José Juan Santamaria Intl
10h 00m
1 stop
ORD12:15 pmChicago O'Hare Intl
Feb 3
ORD1:35 pmChicago O'Hare Intl
19h 45m
1 stop
SJO9:20 amSan José Juan Santamaria Intl
Avianca
Jun 6
SJO1:55 amSan José Juan Santamaria Intl
10h 20m
1 stop
ORD1:15 pmChicago O'Hare Intl
Jun 13
ORD2:35 pmChicago O'Hare Intl
9h 55m
1 stop
SJO11:30 pmSan José Juan Santamaria Intl
Avianca
Jan 22
SJO2:15 amSan José Juan Santamaria Intl
10h 00m
1 stop
ORD12:15 pmChicago O'Hare Intl
Jan 28
ORD2:05 pmChicago O'Hare Intl
10h 10m
1 stop
SJO12:15 amSan 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
Feb 20
SJO1:25 pmSan José Juan Santamaria Intl
10h 33m
1 stop
ORD11:58 pmChicago O'Hare Intl
Feb 26
ORD5:00 amChicago O'Hare Intl
7h 20m
1 stop
SJO12:20 pmSan José Juan Santamaria Intl
Spirit Airlines
Feb 25
SJO1:25 pmSan José Juan Santamaria Intl
10h 33m
1 stop
ORD11:58 pmChicago O'Hare Intl
Mar 4
ORD5:00 amChicago O'Hare Intl
7h 20m
1 stop
SJO12:20 pmSan José Juan Santamaria Intl
Spirit Airlines
May 5
SJO1:41 pmSan José Juan Santamaria Intl
21h 22m
2 stops
ORD12:03 pmChicago O'Hare Intl
May 12
ORD8:42 pmChicago O'Hare Intl
16h 58m
2 stops
SJO12:40 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

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 $365. If you’re not able to fly to Chicago in August, then February is your next best option. Flight prices from San José, San José Province to Chicago during February average around $367.

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 $381. 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 $582.

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 in the morning when prices are around $577.

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 $491 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 $366 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 January 2025, prices for San José, San José Province to Chicago flights are approximately 15% 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

$156

Fastest flight time

5h 25m

Direct flights

Mon, Thu 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 $156. The best round-trip flight deal from San José, San José Province to Chicago found on momondo in the last 72 hours is $287.
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 and Sunday. Airlines offering direct flights are: United Airlines, Lufthansa 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 35m, 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
8,098 reviews
Search Spirit Airlines flights
AviancaPriceFrom $269Free CancellationRating
6.9
2,573 reviews
Search Avianca flights
Copa AirlinesPriceFrom $404Free CancellationRating
7.6
1,658 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $484Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $521Free CancellationRating
8.0
8,511 reviews
Search Delta flights
United AirlinesPriceFrom $557Free CancellationRating
7.4
8,965 reviews
Search United Airlines flights

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.


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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