Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from San José to Chicago from $106

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 to Chicago departing on 10/28. 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

Discover deals from 900+ travel sites with momondo.

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.
Search flight deals

Find the cheapest flights from San José to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
1:30 pm - 12:27 amSJO-ORD
10h 57m1 stop
Spirit Airlines Logo
5:10 am - 12:25 pmORD-SJO
7h 15m1 stop
$189Spirit Airlines
Find Deal
Fri, Nov 7 - Tue, Nov 11
Spirit Airlines Logo
1:30 pm - 12:27 amSJO-ORD
10h 57m1 stop
Spirit Airlines Logo
5:10 am - 12:25 pmORD-SJO
7h 15m1 stop
$203Spirit Airlines
Find Deal
Wed, Nov 5 - Wed, Nov 19
Spirit Airlines Logo
12:34 pm - 12:27 amSJO-ORD
11h 53m2 stops
Spirit Airlines Logo
5:10 am - 12:25 pmORD-SJO
7h 15m1 stop
$212Spirit Airlines
Find Deal
Sat, Nov 8 - Wed, Nov 12
Avianca Logo
5:45 am - 1:15 pmSJO-ORD
7h 30m1 stop
Avianca Logo
4:10 pm - 11:40 pmORD-SJO
7h 30m1 stop
$263Avianca
Find Deal
Fri, Jan 23 - Tue, Jan 27
Multiple Airlines Logo
12:35 pm - 1:03 amSJO-ORD
11h 28m1 stop
Multiple Airlines Logo
5:00 am - 2:17 pmORD-SJO
9h 17m1 stop
$267Multiple Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
Multiple Airlines Logo
12:35 pm - 11:41 amSJO-ORD
22h 06m2 stops
Multiple Airlines Logo
10:52 am - 12:25 pmORD-SJO
25h 33m1 stop
$271Multiple Airlines
Find Deal
Sat, Nov 1 - Wed, Nov 5
Southwest Logo
9:00 am - 8:25 pmSJO-MDW
11h 25m1 stop
Southwest Logo
5:05 am - 1:15 pmMDW-SJO
8h 10m1 stop
$300Southwest
Find Deal
Sat, Dec 6 - Wed, Dec 10
Delta Logo
7:00 am - 4:25 pmSJO-MDW
9h 25m1 stop
Delta Logo
9:30 am - 10:15 pmMDW-SJO
12h 45m2 stops
$301Delta
Find Deal
Sat, Jan 17 - Sat, Jan 24
Southwest Logo
1:45 pm - 10:25 pmSJO-MDW
8h 40m1 stop
Southwest Logo
5:55 am - 7:30 pmMDW-SJO
13h 35m1 stop
$338Southwest
Find Deal
Fri, Feb 6 - Mon, Feb 9
Delta Logo
7:00 am - 10:22 pmSJO-MDW
15h 22m1 stop
Delta Logo
9:30 am - 10:15 pmMDW-SJO
12h 45m2 stops
$386Delta
Find Deal
Mon, Dec 22 - Thu, Jan 22

Spirit Airlines flights from San José to Chicago

Our best Spirit Airlines deals on San José to Chicago flight tickets
Spirit Airlines
Nov 7
SJO1:30 pmSan José Juan Santamaria Intl
10h 57m
1 stop
ORD12:27 amChicago O'Hare Intl
Nov 11
ORD5:10 amChicago O'Hare Intl
7h 15m
1 stop
SJO12:25 pmSan José Juan Santamaria Intl
$189
Find similar
Spirit Airlines
Nov 5
SJO1:30 pmSan José Juan Santamaria Intl
10h 57m
1 stop
ORD12:27 amChicago O'Hare Intl
Nov 19
ORD5:10 amChicago O'Hare Intl
7h 15m
1 stop
SJO12:25 pmSan José Juan Santamaria Intl
$203
Find similar
Spirit Airlines
Nov 8
SJO12:34 pmSan José Juan Santamaria Intl
11h 53m
2 stops
ORD12:27 amChicago O'Hare Intl
Nov 12
ORD5:10 amChicago O'Hare Intl
7h 15m
1 stop
SJO12:25 pmSan José Juan Santamaria Intl
$212
Find similar

American Airlines flights from San José to Chicago

Our best American Airlines deals on San José to Chicago flight tickets
American Airlines
Oct 30
SJO2:40 pmSan José Juan Santamaria Intl
8h 18m
1 stop
ORD11:58 pmChicago O'Hare Intl
Nov 5
ORD5:13 pmChicago O'Hare Intl
5h 00m
SJO10:13 pmSan José Juan Santamaria Intl
$400
Find similar
American Airlines
Oct 30
SJO2:40 pmSan José Juan Santamaria Intl
8h 18m
1 stop
ORD11:58 pmChicago O'Hare Intl
Nov 5
ORD5:13 pmChicago O'Hare Intl
5h 00m
SJO10:13 pmSan José Juan Santamaria Intl
$402
Find similar
American Airlines
Oct 29
SJO6:44 amSan José Juan Santamaria Intl
10h 16m
1 stop
ORD6:00 pmChicago O'Hare Intl
Nov 5
ORD5:13 pmChicago O'Hare Intl
5h 00m
SJO10:13 pmSan José Juan Santamaria Intl
$405
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San José 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 October 16, 2025.
Use the filters below to find and compare flights from San José 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

Fri 11/7

1:30 pm-12:27 am

1 stop10h 57m

Chicago O'Hare Intl

Tue 11/11

5:10 am-12:25 pm

1 stop7h 15m

$189

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 11/5

1:30 pm-12:27 am

1 stop10h 57m

Chicago O'Hare Intl

Wed 11/19

5:10 am-12:25 pm

1 stop7h 15m

$203

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 11/8

12:34 pm-12:27 am

2 stops11h 53m

Chicago O'Hare Intl

Wed 11/12

5:10 am-12:25 pm

1 stop7h 15m

$212

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 1/23

5:45 am-1:15 pm

1 stop7h 30m

Chicago O'Hare Intl

Tue 1/27

4:10 pm-11:40 pm

1 stop7h 30m

$263

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 10/30

12:35 pm-1:03 am

1 stop11h 28m

Chicago O'Hare Intl

Sun 11/2

5:00 am-2:17 pm

1 stop9h 17m

$267

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 11/1

12:35 pm-11:41 am

2 stops22h 06m

Chicago O'Hare Intl

Wed 11/5

10:52 am-12:25 pm

1 stop25h 33m

$271

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 12/6

9:00 am-8:25 pm

1 stop11h 25m

Chicago Midway

Wed 12/10

5:05 am-1:15 pm

1 stop8h 10m

$300

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/17

7:00 am-4:25 pm

1 stop9h 25m

Chicago Midway

Sat 1/24

9:30 am-10:15 pm

2 stops12h 45m

$301

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 2/6

1:45 pm-10:25 pm

1 stop8h 40m

Chicago Midway

Mon 2/9

5:55 am-7:30 pm

1 stop13h 35m

$338

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 12/22

7:00 am-10:22 pm

1 stop15h 22m

Chicago Midway

Thu 1/22

9:30 am-10:15 pm

2 stops12h 45m

$386

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from San José 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 November is, on average, the cheapest month to fly to Chicago from San José, with most prices found around $411. If you’re not able to fly to Chicago in November, then October is your next best option. Flight prices from San José to Chicago during October average around $430.

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 Thursday when prices can be found for as low as $420. 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 to Chicago for around $593.

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 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 $545.

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 when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $465 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 for as low as $387 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 to Chicago flights?

You could potentially save up to 25% on your flight if you consider stops on a San José to Chicago flight.

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

As of October 2025, prices for San José to Chicago flights are approximately 27% more expensive when compared to flights at the same time last year.

When to book flights from San José to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from San José to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap San José to Chicago (SJO to CHI) flight deals and tips

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

Best Price Found

$236

Fastest flight time

5h 29m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from San José in the past 72 hours is $236. The best round-trip flight deal from San José to Chicago found on momondo in the last 72 hours is $324.
The fastest flight from San José to Chicago takes 5h 29m
Direct flights go from San José to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
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 30m, 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 to Chicago?

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

Best airlines flying from San José to Chicago

Compare and see reviews for airlines that fly from San José to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $237Free CancellationRating
6.3
8,099 reviews
Search Spirit Airlines flights
AviancaPriceFrom $249Free CancellationRating
6.6
2,452 reviews
Search Avianca flights
Copa AirlinesPriceFrom $314Free CancellationRating
7.6
1,551 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $324Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights
SouthwestPriceFrom $425Free CancellationRating
8.0
4,241 reviews
Search Southwest flights
United AirlinesPriceFrom $434Free CancellationRating
7.4
8,982 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
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.

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 11/15
Sat 11/22
By creating a price alert you accept our terms of use and privacy policy.

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