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Cheap flights from San Jose Juan Santamaria to Chicago

Compare San Jose Juan Santamaria to Chicago flight deals

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Flight deals from San Jose Juan Santamaria to Chicago

Looking for a cheap last-minute deal or the best return flight from San Jose Juan Santamaria to Chicago? Find the lowest prices on one-way and return tickets right here.
Chicago.P10,812 per passenger.Departing Sat, 6 Dec, returning Mon, 8 Dec.Return flight with Viva and Spirit Airlines.Outbound indirect flight with Viva, departs from San Jose Juan Santamaria on Sat, 6 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 8 Dec, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P10,812, select.
Chicago.P11,666 per passenger.Departing Wed, 5 Nov, returning Tue, 11 Nov.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Wed, 5 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 11 Nov, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P11,666, select.
Chicago.P12,016 per passenger.Departing Fri, 31 Oct, returning Tue, 11 Nov.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Fri, 31 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 11 Nov, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P12,016, select.
Chicago.P12,547 per passenger.Departing Wed, 19 Nov, returning Mon, 8 Dec.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Wed, 19 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 8 Dec, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P12,547, select.
Chicago.P13,057 per passenger.Departing Wed, 14 Jan, returning Wed, 4 Feb.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Wed, 14 Jan, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Wed, 4 Feb, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P13,057, select.
Chicago.P13,060 per passenger.Departing Wed, 14 Jan, returning Tue, 27 Jan.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Wed, 14 Jan, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 27 Jan, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P13,060, select.
Chicago.P13,720 per passenger.Departing Thu, 25 Dec, returning Mon, 12 Jan.Return flight with Spirit Airlines and Viva.Outbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Thu, 25 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Viva, departs from Chicago O'Hare International on Mon, 12 Jan, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P13,720, select.
Chicago.P14,803 per passenger.Departing Wed, 4 Feb, returning Sat, 7 Feb.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Wed, 4 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 7 Feb, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P14,803, select.
Chicago.P16,714 per passenger.Departing Wed, 29 Oct, returning Fri, 31 Oct.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Wed, 29 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Fri, 31 Oct, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P16,714, select.
Chicago.P18,633 per passenger.Departing Thu, 18 Dec, returning Sun, 8 Feb.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Thu, 18 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sun, 8 Feb, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P18,633, select.
Chicago.P21,767 per passenger.Departing Wed, 24 Dec, returning Thu, 1 Jan.Return flight with United.Outbound direct flight with United departs from San Jose Juan Santamaria on Wed, 24 Dec, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Thu, 1 Jan, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P21,767, select.
Chicago.P22,687 per passenger.Departing Mon, 22 Dec, returning Wed, 31 Dec.Return flight with United.Outbound direct flight with United departs from San Jose Juan Santamaria on Mon, 22 Dec, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 31 Dec, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P22,687, select.
Chicago.P22,952 per passenger.Departing Mon, 4 May, returning Sun, 10 May.Return flight with Avianca.Outbound indirect flight with Avianca, departs from San Jose Juan Santamaria on Mon, 4 May, arriving in Chicago O'Hare International.Inbound indirect flight with Avianca, departs from Chicago O'Hare International on Sun, 10 May, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P22,952, select.
Chicago.P26,981 per passenger.Departing Sat, 15 Nov, returning Sat, 29 Nov.Return flight with United.Outbound direct flight with United departs from San Jose Juan Santamaria on Sat, 15 Nov, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 29 Nov, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From P26,981, select.

Find the cheapest month to fly from San Jose Juan Santamaria to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like San Jose Juan Santamaria to Chicago flights are currently cheapest in December.
Oct
from P16,714
Nov
from P11,666
Dec
from P10,812
Jan
from P13,060
Feb
from P14,803
Mar
from P28,143
Apr
from P28,485
May
from P22,952
Jun
Find prices
Jul
from P38,656
Aug
Find prices
Sep
Find prices

Direct flights from San Jose Juan Santamaria to Chicago

Alternative San Jose Juan Santamaria to Chicago routes

Looking for the cheapest, fastest or easiest route from San Jose Juan Santamaria to Chicago? You could fly into the following airports instead.

San Jose to Chicago: Flight information

The things to know before you go.
Cheapest flight foundP10,812
Cheapest month to flyDecember
Average flight time5 hrs, 32 mins
Most popular airlineAmerican Airlines
Average flights per week9

Finding cheap flights from San Jose Juan Santamaria to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from San Jose Juan Santamaria to Chicago is P10,812. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
5 hours and 32 minutes is the average flight time from San Jose Juan Santamaria to Chicago.
American Airlines and United fly direct from San Jose Juan Santamaria to Chicago.
As of October 2025, there are 9 flights per week flying from San Jose Juan Santamaria to Chicago.
The cheapest month to fly from San Jose Juan Santamaria to Chicago is usually December.
If you're flying from San Jose Juan Santamaria Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from P10,812.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from San Jose Juan Santamaria Airport to Chicago on Saturday, 6 December 2025.
Yes – the average flight time is 5 hours and 32 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In October, the average temperature is usually around 11°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Viva and United offer the cheapest flight tickets to Chicago.

Travelling from Juan Santamaria International Airport (SJO) to Chicago: what you need to know

  • The average duration of a direct flight from Juan Santamaria International Airport to Chicago is 5 hours 20 minutes.

  • The timezone in Chicago is UTC-5. The city is one hour ahead of San Jose, where Juan Santamaria International Airport is located.

  • Leave enough time to get on your SJO to Chicago flight. Generally, it's best to arrive two hours before international departures and an hour ahead for domestic flights.

  • Planning to travel during a peak time like school or public holidays? Expect longer queues at security and check-in. Give yourself extra leeway and arrive up to four hours before international flights and two hours ahead of domestic departures.

  • You can book a direct Juan Santamaria International Airport to Chicago ticket. Start your trip at SJO and land at O'Hare International Airport (ORD).

  • Keep your eyes peeled for offers from United Airlines. This airline has direct flights from Juan Santamaria International Airport to Chicago.

  • Stopovers are the ideal opportunity to take a break from travelling and perhaps even explore a different city. When searching for plane tickets from SJO to Chicago, deselect the 'Direct flights only' box to see where you can visit along the way. Consider one of these popular options:

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • Los Angeles International Airport (LAX)

    • Orlando International Airport (MCO)

  • Located around 14 kilometres from the centre of San Jose, SJO can be reached in about 20 minutes by car. The journey on public transport will take roughly 2 hours 20 minutes.

  • Want a leisurely start to your holiday? Stay near SJO. Whether you're boarding an early flight from Juan Santamaria International Airport to Chicago or want to avoid feeling rushed, these hotels put convenience first:

  • 79.83% of flights that depart Juan Santamaria International Airport touch down at their destination on time.

How to find the cheapest flights from Juan Santamaria International Airport (SJO) to Chicago

  • P6,026 is the lowest price we've seen for a one-way Juan Santamaria International Airport to Chicago flight. A round-trip ticket right now is P10,812. Depending on how early you book and the availability, these fares could change.

  • To score cheap flights from SJO to Chicago, reserve your trip nine months before your planned departure.

  • Organise your trip for January. That's the best month for landing an epic deal on Juan Santamaria International Airport to Chicago tickets. If you're flexible on when you fly, use the 'Whole month' tool to access the cheapest price across every month.

  • Stay on top of deals for cheap flights from SJO to Chicago by setting up a Price Alert. You'll get an email or push notification on the app when a lower fare becomes available.

  • Find a cheap flight from Juan Santamaria International Airport to Chicago with the help of our filters. Choose your preferred times, number of stops and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It'll take you about 35 minutes to reach the centre driving.

  • When travelling by public transport, expect a journey time of around 55 minutes.

  • The last thing you need is a lengthy journey to your hotel if you're landing late on a flight from Juan Santamaria International Airport to Chicago. Stay at one of these accommodation options near ORD instead:

  • Grab an O'Hare International Airport rental car and explore Chicago and beyond with your own set of wheels. Routes Car Rentals, Dollar and Budget are well-known companies you can book with here.

  • Get the best deal by booking your vehicle from O'Hare International Airport about four weeks ahead of your flight from SJO to Chicago.

  • The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • After your flight from Juan Santamaria International Airport to Chicago has touched down, you can make your way to the city centre in about 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).

  • If you choose to travel on public transport, the journey will take you 45 minutes or so.

  • After stepping off your SJO to Chicago flight, settle in at a hotel close to MDW. These are some comfortable accommodation options that'll help you get into relaxation mode:

  • The fastest way to reach your destination is with a Chicago Midway International Airport rental car. Grab a set of wheels from Dollar, Hertz or Budget and set off in the blink of an eye.

  • Score the best price by reserving your ride from MDW four weeks in advance. You can also expect to have a greater selection of vehicles.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Head to the city centre after your flight from Juan Santamaria International Airport to Chicago has landed. Central Chicago is about 137 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to reach by cab or ride-share.

  • The journey will take you roughly 4 hours 15 minutes by public transport.

  • Stay at a hotel close to RFD and go from the runway to resting in a snap. Whether you're arriving on a late SJO to Chicago flight or just want an easier arrival, these accommodation options put comfort right within reach:

  • Begin your travels without worrying about how to get to your destination with a Chicago Rockford International Airport rental car. Book your ideal wheels with trusted names here like Budget, Alamo and National.

  • Rental providers sometimes offer deals on early bookings, so secure your vehicle from RFD ahead of your flight from Juan Santamaria International Airport to Chicago. A little prep today saves cash tomorrow.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

  • Visit Chicago during peak season if you like a lively atmosphere, but remember that hotel prices are typically higher. Alternatively, book your flights from Juan Santamaria International Airport to Chicago during the off-season when prices are cheaper and it's not as busy.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Book your Juan Santamaria International Airport to Chicago plane ticket then if that's your ideal forecast.

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for a cheap ticket from SJO to Chicago around that time if you want to travel in cooler conditions.

More about Chicago

Explore more of United States

  • Chicago has plenty going for it, but there are so many other corners of United States you'll want to see. About 451 kilometres south-east of Chicago, a visit to Columbus will keep your itinerary busy. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. Get a taste of what this destination has to offer at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from San Jose to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.