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Cheap flights from San José to Chicago O'Hare Intl Airport from £167

SJO — ORD
23 Oct — 30 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from San José to O'Hare Intl

Enter your travel dates to find the best prices.

Cheapest flights from San José to O'Hare Intl

Sat 7/1113:55 -
Nonstop5h 33m
Sat 14/1119:55 -
1 stop17h 27m
Deal found 22/9£288
Wed 4/1101:50 -
1 stop18h 40m
Sun 8/1122:30 -
1 stop10h 20m
Deal found 19/9£288
Wed 21/1010:03 -
1 stop13h 54m
Mon 2/1114:13 -
1 stop22h 06m
Deal found 23/9£289
Sat 31/1013:05 -
Nonstop5h 33m
Sat 7/1113:00 -
1 stop17h 25m
Deal found 23/9£291
Thu 24/1223:28 -
1 stop17h 24m
Sun 10/107:02 -
Nonstop5h 13m
Deal found 22/9£291
Mon 21/1213:25 -
Nonstop5h 32m
Wed 30/1221:43 -
1 stop24h 49m
Deal found 23/9£302
Thu 19/1110:03 -
1 stop14h 08m
Wed 25/1114:13 -
1 stop20h 46m
Deal found 21/9£303
Thu 24/1217:53 -
1 stop18h 53m
Sun 10/114:13 -
1 stop16h 49m
Deal found 22/9£305
Wed 23/1214:15 -
1 stop26h 40m
Wed 30/1221:43 -
1 stop24h 49m
Deal found 23/9£311
Thu 24/1201:15 -
1 stop10h 00m
Wed 30/1221:43 -
1 stop24h 49m
Deal found 20/9£312
Tue 22/1206:40 -
1 stop16h 19m
Tue 29/1221:43 -
1 stop24h 49m
Deal found 22/9£322

Find flight deals from San José to O'Hare Intl

Round-trip from

£282

One-way from

£167

Popular in

July

Cheapest in

February

Average price

£375
2/3-8/3
  • 2/3-8/3
  • 2 total stops
  • 41h 33m total
  • San José to Chicago
Search Deals
9/2-31/12
  • 9/2-31/12
  • 1 total stop
  • 18h 58m total
  • San José to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (£41 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£8 potential savings vs. average return price).
Search Deals
Average for round-trip flights in September 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from San José to Chicago O'Hare Intl Airport that are best for you.

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Fly to

Route

Depart

Return

Price

Cheapest return flight

San JoséChicago

SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl

SJOORD

San José Juan Santamaria Intl

Tue 9/2

16:15-11:13

1 stop18h 58m

Chicago O'Hare Intl

Wed 31/12

00:00-00:00

Nonstop0h 00m

£167

San JoséChicago

SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl

SJOORD

San José Juan Santamaria Intl

Tue 9/3

13:25-18:57

Nonstop5h 32m

Chicago O'Hare Intl

Tue 16/3

09:25-19:39

1 stop11h 14m

£288

San JoséChicago

SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl

SJOORD

San José Juan Santamaria Intl

Fri 6/11

08:44-00:11

1 stop15h 27m

Chicago O'Hare Intl

Fri 13/11

14:13-10:59

1 stop20h 46m

£289

San JoséChicago

SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl

SJOORD

San José Juan Santamaria Intl

Tue 22/12

13:25-18:57

Nonstop5h 32m

Chicago O'Hare Intl

Wed 30/12

21:43-22:32

1 stop24h 49m

£291

San JoséChicago

SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl

SJOORD

San José Juan Santamaria Intl

Tue 12/1

01:15-16:25

1 stop15h 10m

Chicago O'Hare Intl

Wed 20/1

07:02-12:15

Nonstop5h 13m

£295

San JoséChicago

SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl

SJOORD

San José Juan Santamaria Intl

Sun 29/11

16:15-11:13

1 stop18h 58m

Chicago O'Hare Intl

Wed 31/12

00:00-00:00

Nonstop0h 00m

£297

San JoséChicago

SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl

SJOORD

San José Juan Santamaria Intl

Sun 10/1

15:05-23:42

1 stop8h 37m

Chicago O'Hare Intl

Wed 31/12

00:00-00:00

Nonstop0h 00m

£305

San JoséChicago

SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl

SJOORD

San José Juan Santamaria Intl

Mon 21/12

14:15-16:54

1 stop26h 39m

Chicago O'Hare Intl

Wed 30/12

21:43-22:32

1 stop24h 49m

£311

San JoséChicago

SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl

SJOORD

San José Juan Santamaria Intl

Wed 23/12

14:15-16:55

1 stop26h 40m

Chicago O'Hare Intl

Wed 30/12

21:43-22:32

1 stop24h 49m

£311

San JoséChicago

SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl

SJOORD

San José Juan Santamaria Intl

Mon 30/11

17:55-12:46

1 stop18h 51m

Chicago O'Hare Intl

Fri 4/12

14:13-11:02

1 stop20h 49m

£324

Flights are sorted by cheapest return flights first.

Deals found on 22/9

Showing 1-10 of 21 resultsSorted by cheapest first
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Best time to book a flight from San José to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from San José with our price prediction graph.
Estimated return price

Cheapflights Insights

Everything you need to know about your flight from San José to Chicago O'Hare Intl Airport

How far ahead should I book a flight from San José to Chicago O'Hare Intl Airport?

Booking 89 days in advance of your planned departure date is, on average, the best time to get cheap flights from San José to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from San José to Chicago O'Hare Intl Airport?

Currently, February is the cheapest month in which you can book a flight from San José to Chicago O'Hare Intl Airport (average of £304). Flying from San José to Chicago O'Hare Intl Airport in July is currently the most expensive (average of £484). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost for a return flight from San José to Chicago O'Hare Intl Airport?

Airfare is below average for this route at the moment.

San José to Chicago O'Hare Intl Airport flights typically cost between £296 and £453 in March.
The cheapest return price found within the last 5 days was £282 on Multiple Airlines (2 Mar–8 Mar).

Related info for your journey

  • What airport do you fly from for flights from San José to Chicago O'Hare Intl?

    If you book a flight to Chicago O'Hare Intl from San José, you will be flying from Juan Santamaria Intl, which is the city’s only airport. San José Juan Santamaria Intl (SJO) is located 8.8 mi from the center of San José. There are 0 flights from Juan Santamaria Intl to Chicago O'Hare Intl per day from 0 different airlines.

  • How long is the flight from San José to Chicago O'Hare Intl Airport?

    Departing from San José to Chicago O'Hare Intl Airport will take you 5h 32m. The distance between San José and Chicago O'Hare Intl Airport is about 2220 mi. All flights are typically direct.

  • Can I find deals for flights from San José to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on San José to O'Hare Intl flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from San José to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San José to O'Hare Intl.

  • Can I find deals for business class flights from San José to O'Hare Intl?

    Yes. Cheapflights offers flight deals from San José to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San José to Chicago O'Hare Intl Airport?

    Currently, February is the cheapest month in which you can book a flight from San José to Chicago O'Hare Intl Airport (average of £304). Flying from San José to Chicago O'Hare Intl Airport in July is currently the most expensive (average of £484). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Travelling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Elk Grove Village

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Why should you use Cheapflights to find cheap flight tickets from San José to O'Hare Intl?

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Can Cheapflights find flights from San José to O'Hare Intl with no change fees?

Certainly. Search results for flights to O'Hare Intl from San José shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from San José to O'Hare Intl become cheaper?

Yes! Start tracking prices for San José to O'Hare Intl flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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