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Cheap flights from San José, San José Province to Chicago from $137

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 8/19. 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

Spirit Airlines Logo
12:19 pm - 10:48 pmSJO-ORD
9h 29m1 stop
Spirit Airlines Logo
5:05 am - 11:14 amORD-SJO
7h 09m1 stop
$233Spirit Airlines
Find Deal
Wed, Sep 24 - Thu, Oct 2
Logo
7:30 am - 10:22 pmSJO-ORD
13h 52m1 stop
Logo
6:56 am - 3:13 pmORD-SJO
9h 17m1 stop
$234
Find Deal
Wed, Aug 20 - Sun, Aug 24
Spirit Airlines Logo
12:18 pm - 11:59 pmSJO-ORD
10h 41m1 stop
Spirit Airlines Logo
8:12 pm - 11:12 amORD-SJO
16h 00m1 stop
$235Spirit Airlines
Find Deal
Wed, Aug 27 - Sat, Aug 30
Logo
7:30 am - 10:22 pmSJO-ORD
13h 52m1 stop
Logo
6:56 am - 3:13 pmORD-SJO
9h 17m1 stop
$236
Find Deal
Wed, Aug 20 - Wed, Aug 27
Logo
7:30 am - 10:22 pmSJO-ORD
13h 52m1 stop
Logo
6:56 am - 3:13 pmORD-SJO
9h 17m1 stop
$237
Find Deal
Wed, Aug 20 - Wed, Aug 27
Spirit Airlines Logo
12:18 pm - 11:59 pmSJO-ORD
10h 41m1 stop
Spirit Airlines Logo
8:12 pm - 11:12 amORD-SJO
16h 00m1 stop
$238Spirit Airlines
Find Deal
Tue, Aug 26 - Sat, Aug 30
Frontier Logo
1:47 pm - 1:47 pmSJO-MDW
23h 00m1 stop
Frontier Logo
6:00 am - 1:32 pmMDW-SJO
7h 32m1 stop
$351Frontier
Find Deal
Sat, Aug 16 - Sat, Dec 6
Frontier Logo
1:47 pm - 1:47 pmSJO-MDW
23h 00m1 stop
Frontier Logo
6:10 am - 12:24 pmMDW-SJO
7h 14m1 stop
$372Frontier
Find Deal
Sat, Aug 16 - Sat, Aug 23
Southwest Logo
1:40 pm - 11:20 pmSJO-MDW
8h 40m1 stop
Southwest Logo
6:25 am - 6:55 pmMDW-SJO
13h 30m1 stop
$384Southwest
Find Deal
Wed, Sep 24 - Tue, Sep 30
Southwest Logo
8:50 am - 7:45 pmSJO-MDW
9h 55m2 stops
Southwest Logo
9:10 am - 6:55 pmMDW-SJO
10h 45m1 stop
$388Southwest
Find Deal
Wed, Sep 24 - Tue, Sep 30

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
Sep 24
SJO12:19 pmSan José Juan Santamaria Intl
9h 29m
1 stop
ORD10:48 pmChicago O'Hare Intl
Oct 2
ORD5:05 amChicago O'Hare Intl
7h 09m
1 stop
SJO11:14 amSan José Juan Santamaria Intl
$233
Find similar
Spirit Airlines
Aug 27
SJO12:18 pmSan José Juan Santamaria Intl
10h 41m
1 stop
ORD11:59 pmChicago O'Hare Intl
Aug 30
ORD8:12 pmChicago O'Hare Intl
16h 00m
1 stop
SJO11:12 amSan José Juan Santamaria Intl
$235
Find similar
Spirit Airlines
Aug 26
SJO12:18 pmSan José Juan Santamaria Intl
10h 41m
1 stop
ORD11:59 pmChicago O'Hare Intl
Aug 30
ORD8:12 pmChicago O'Hare Intl
16h 00m
1 stop
SJO11:12 amSan José Juan Santamaria Intl
$238
Find similar

Frontier flights from San José, San José Province to Chicago

Our best Frontier deals on San José, San José Province to Chicago flight tickets
Frontier
Aug 9
SJO1:47 pmSan José Juan Santamaria Intl
19h 38m
1 stop
ORD10:25 amChicago O'Hare Intl
Dec 6
ORD5:10 amChicago O'Hare Intl
8h 22m
1 stop
SJO1:32 pmSan José Juan Santamaria Intl
$330
Find similar
Frontier
Aug 2
SJO1:47 pmSan José Juan Santamaria Intl
8h 42m
1 stop
ORD11:29 pmChicago O'Hare Intl
Aug 9
ORD5:01 amChicago O'Hare Intl
8h 30m
1 stop
SJO12:31 pmSan José Juan Santamaria Intl
$349
Find similar
Frontier
Aug 2
SJO1:47 pmSan José Juan Santamaria Intl
8h 42m
1 stop
ORD11:29 pmChicago O'Hare Intl
Aug 9
ORD5:01 amChicago O'Hare Intl
8h 30m
1 stop
SJO12:31 pmSan José Juan Santamaria Intl
$350
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San José, San José Province to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from San José, San José Province to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 9/24

12:19 pm-10:48 pm

1 stop9h 29m

Chicago O'Hare Intl

Thu 10/2

5:05 am-11:14 am

1 stop7h 09m

$233

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 8/20

7:30 am-10:22 pm

1 stop13h 52m

Chicago O'Hare Intl

Sun 8/24

6:56 am-3:13 pm

1 stop9h 17m

$234

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 8/27

12:18 pm-11:59 pm

1 stop10h 41m

Chicago O'Hare Intl

Sat 8/30

8:12 pm-11:12 am

1 stop16h 00m

$235

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 8/20

7:30 am-10:22 pm

1 stop13h 52m

Chicago O'Hare Intl

Wed 8/27

6:56 am-3:13 pm

1 stop9h 17m

$236

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 8/20

7:30 am-10:22 pm

1 stop13h 52m

Chicago O'Hare Intl

Wed 8/27

6:56 am-3:13 pm

1 stop9h 17m

$237

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 8/26

12:18 pm-11:59 pm

1 stop10h 41m

Chicago O'Hare Intl

Sat 8/30

8:12 pm-11:12 am

1 stop16h 00m

$238

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 8/16

1:47 pm-1:47 pm

1 stop23h 00m

Chicago Midway

Sat 12/6

6:00 am-1:32 pm

1 stop7h 32m

$351

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 8/16

1:47 pm-1:47 pm

1 stop23h 00m

Chicago Midway

Sat 8/23

6:10 am-12:24 pm

1 stop7h 14m

$372

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/24

1:40 pm-11:20 pm

1 stop8h 40m

Chicago Midway

Tue 9/30

6:25 am-6:55 pm

1 stop13h 30m

$384

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/24

8:50 am-7:45 pm

2 stops9h 55m

Chicago Midway

Tue 9/30

9:10 am-6:55 pm

1 stop10h 45m

$388

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 August is, on average, the cheapest month to fly to Chicago from San José, San José Province, with most prices found around $436. 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 $443.

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 $432. 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 $639.

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 $597.

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 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $480 when searching 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 $401 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.

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

You could potentially save up to 82% 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 July 2025, prices for San José, San José Province to Chicago flights are approximately 10% 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

$137

Fastest flight time

7h 35m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from San José, San José Province in the past 72 hours is $137. The best round-trip flight deal from San José, San José Province to Chicago found on momondo in the last 72 hours is $233.
The fastest flight from San José, San José Province to Chicago takes 7h 35m
Direct flights go from San José, San José Province to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • 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
AviancaPriceFrom $261Free CancellationRating
6.7
2,388 reviews
Search Avianca flights
Spirit AirlinesPriceFrom $266Free CancellationRating
6.3
8,048 reviews
Search Spirit Airlines flights
Copa AirlinesPriceFrom $314Free CancellationRating
7.5
1,493 reviews
Search Copa Airlines flights
SouthwestPriceFrom $425Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
United AirlinesPriceFrom $437Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
American AirlinesPriceFrom $446Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • Avianca Flights From San José, San José Province to Chicago

    The lowest priced Avianca flight from San José, San José Province to Chicago from the last 72 hours was $261. Generally, Avianca has 3 flights on this route every week with an average price of $462. Avianca is rated 6.7/10 by our users.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport