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Cheap Flights from San Jose (SJO) to Chicago (CHIA)

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 Airport to Chicago? If you want to travel next month, return fares start from $511. Find the lowest prices on one-way and return tickets right here.
Chicago.$459 per passenger.Departing Sat, 15 Aug, returning Mon, 17 Aug.Return flight with Viva.Outbound indirect flight with Viva, departs from San Jose Juan Santamaria on Sat, 15 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Viva, departs from Chicago O'Hare International on Mon, 17 Aug, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $459, select.
Chicago.$491 per passenger.Departing Sat, 15 Aug, returning Fri, 4 Sep.Return flight with Viva.Outbound indirect flight with Viva, departs from San Jose Juan Santamaria on Sat, 15 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Viva, departs from Chicago O'Hare International on Fri, 4 Sep, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $491, select.
Chicago.$509 per passenger.Departing Wed, 22 Jul, returning Fri, 21 Aug.Return flight with Copa.Outbound indirect flight with Copa, departs from San Jose Juan Santamaria on Wed, 22 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Copa, departs from Chicago O'Hare International on Fri, 21 Aug, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $509, select.
Chicago.$510 per passenger.Departing Fri, 2 Oct, returning Fri, 9 Oct.Return flight with Copa.Outbound indirect flight with Copa, departs from San Jose Juan Santamaria on Fri, 2 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Copa, departs from Chicago O'Hare International on Fri, 9 Oct, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $510, select.
Chicago.$510 per passenger.Departing Sat, 23 May, returning Sat, 6 Jun.Return flight with Copa.Outbound indirect flight with Copa, departs from San Jose Juan Santamaria on Sat, 23 May, arriving in Chicago O'Hare International.Inbound indirect flight with Copa, departs from Chicago O'Hare International on Sat, 6 Jun, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $510, select.
Chicago.$510 per passenger.Departing Tue, 14 Jul, returning Tue, 21 Jul.Return flight with Copa.Outbound indirect flight with Copa, departs from San Jose Juan Santamaria on Tue, 14 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Copa, departs from Chicago O'Hare International on Tue, 21 Jul, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $510, select.
Chicago.$510 per passenger.Departing Sun, 20 Sep, returning Sat, 26 Sep.Return flight with Copa.Outbound indirect flight with Copa, departs from San Jose Juan Santamaria on Sun, 20 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Copa, departs from Chicago O'Hare International on Sat, 26 Sep, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $510, select.
Chicago.$510 per passenger.Departing Mon, 18 May, returning Mon, 25 May.Return flight with Copa.Outbound indirect flight with Copa, departs from San Jose Juan Santamaria on Mon, 18 May, arriving in Chicago O'Hare International.Inbound indirect flight with Copa, departs from Chicago O'Hare International on Mon, 25 May, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $510, select.
Chicago.$511 per passenger.Departing Sat, 17 Oct, returning Tue, 10 Nov.Return flight with Copa.Outbound indirect flight with Copa, departs from San Jose Juan Santamaria on Sat, 17 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Copa, departs from Chicago O'Hare International on Tue, 10 Nov, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $511, select.
Chicago.$511 per passenger.Departing Wed, 3 Jun, returning Fri, 5 Jun.Return flight with Copa.Outbound indirect flight with Copa, departs from San Jose Juan Santamaria on Wed, 3 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Copa, departs from Chicago O'Hare International on Fri, 5 Jun, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $511, select.
Chicago.$516 per passenger.Departing Fri, 15 Jan, returning Mon, 18 Jan.Return flight with United.Outbound indirect flight with United, departs from San Jose Juan Santamaria on Fri, 15 Jan, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Mon, 18 Jan, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $516, select.
Chicago.$517 per passenger.Departing Tue, 23 Feb, returning Sun, 28 Feb.Return flight with United.Outbound indirect flight with United, departs from San Jose Juan Santamaria on Tue, 23 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Sun, 28 Feb, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $517, select.
Chicago.$561 per passenger.Departing Thu, 24 Sep, returning Thu, 1 Oct.Return flight with United.Outbound indirect flight with United, departs from San Jose Juan Santamaria on Thu, 24 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Thu, 1 Oct, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $561, select.
Chicago.$583 per passenger.Departing Tue, 9 Mar, returning Sat, 13 Mar.Return flight with Copa.Outbound indirect flight with Copa, departs from San Jose Juan Santamaria on Tue, 9 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Copa, departs from Chicago O'Hare International on Sat, 13 Mar, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $583, select.
Chicago.$583 per passenger.Departing Thu, 3 Dec, returning Thu, 10 Dec.Return flight with Copa.Outbound indirect flight with Copa, departs from San Jose Juan Santamaria on Thu, 3 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Copa, departs from Chicago O'Hare International on Thu, 10 Dec, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $583, select.
Chicago.$584 per passenger.Departing Tue, 10 Nov, returning Sun, 15 Nov.Return flight with Copa.Outbound indirect flight with Copa, departs from San Jose Juan Santamaria on Tue, 10 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Copa, departs from Chicago O'Hare International on Sun, 15 Nov, arriving in San Jose Juan Santamaria.Price includes taxes and charges.From $584, 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 August.
May
from $510
Jun
from $511
Jul
from $510
Aug
from $459
Sep
from $510
Oct
from $510
Nov
from $584
Dec
from $583
Jan
from $516
Feb
from $517
Mar
from $583
Apr
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.

Chicago Midway

14km from central Chicago
Closest
from $596
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from $459
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
Search flights

San Jose to Chicago: Flight information

The things to know before you go.
Cheapest flight found$459
Cheapest month to flyAugust
Average flight time5 hrs, 31 mins
Most popular airlineAmerican Airlines
Average flights per week7

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 $459. 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.
United flies direct from San Jose Juan Santamaria to Chicago.
As of May 2026, there are 7 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 August.
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 $459.
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, 15 August 2026.
Yes – the average flight time is 5 hours and 31 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 May, the average temperature is usually around 13°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

  • Approximately 5 hours 10 minutes is how long you can expect to be in the air on a direct flight from Juan Santamaria International Airport to Chicago.

  • San Jose (the location of Juan Santamaria International Airport) and Chicago share the same timezone — UTC-6.

  • You can pick from five weekly services between Juan Santamaria International Airport (SJO) and Chicago O'Hare International Airport (ORD). This is the most popular flight route.

  • To avoid missing your SJO to Chicago flight, leave plenty of time to check in and drop off your luggage. Turning up two hours before international departures and an hour before domestic flights is the standard rule.

  • During popular months such as January, it's a good idea to get to the airport earlier than usual. Plan to arrive two hours before domestic departures and four hours ahead of an international flight whenever you're travelling during peak periods in general.

  • Direct Juan Santamaria International Airport to Chicago tickets are available for booking. Chicago O'Hare International Airport (ORD) is where you'll complete your journey.

  • American Airlines is a well-known airline that offers direct flights from Juan Santamaria International Airport to Chicago.

  • A stopover is the ideal opportunity to take a break from travelling and perhaps even explore another 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:

    • Atlanta Hartsfield-Jackson 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 25 minutes by car (depending on traffic). Travelling on public transport takes roughly 1 hour.

  • Want a relaxed start to your travels? Stay near SJO. Whether you're taking an early flight from Juan Santamaria International Airport to Chicago or don't want departure day to feel hectic, these hotels are just the thing:

  • 79% of flights departing from Juan Santamaria International Airport land at their destination on time.

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

  • The best price we've found for a one-way Juan Santamaria International Airport to Chicago flight is $216. The cheapest price for a return flight is $459. Keep in mind fares may change due to availability at the time of booking.

  • To score cheap flights from SJO to Chicago, book your trip eight months ahead of your departure.

  • January is the best month for landing an amazing deal on Juan Santamaria International Airport to Chicago tickets. If you want to travel at a different time of year, the 'Whole month' tool will show you the lowest prices across every month.

  • Spend less time searching for cheap flights from SJO to Chicago by creating a Price Alert. We'll send you an email or push notification on the app when a new discounted fare appears.

  • Pick your ideal arrival and departure times, number of stops and airlines with our filters. Then, sort the results for your flight from Juan Santamaria International Airport to Chicago by 'Fastest,' 'Cheapest' or 'Best.'

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) to central Chicago takes around 30 minutes to reach by car. The centre is roughly 27 kilometres away.

  • Travelling on public transport takes around 45 minutes.

  • Consider staying in a hotel close to ORD if you're coming in on a late flight from Juan Santamaria International Airport to Chicago. Select one of these accommodation options and make your arrival easier:

  • For the best deal, reserve your vehicle from Chicago O'Hare International Airport about four weeks ahead of your flight from SJO to Chicago.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is about 16 kilometres from Chicago Midway International Airport (MDW). After your flight from Juan Santamaria International Airport to Chicago has landed and you've navigated your way to arrivals, the drive should be around 25 minutes.

  • If you travel by public transport, you'll reach the centre in 30 minutes or so.

  • Following your SJO to Chicago flight, kick back at a hotel close to MDW. These are some great accommodation options that'll help you sink into relaxation mode:

  • Avoid paying more than you need to. Reserving your ride four weeks before your arrival at MDW will help you save.

  • Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Make tracks for the city centre after your flight from Juan Santamaria International Airport to Chicago has arrived. Central Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to get to by car.

  • If you go by public transport, the journey time is around 2 hours.

  • Enjoy a low-stress, comfortable start to your trip by checking in to a hotel near RFD after your SJO to Chicago flight. Recover from a day of travel or simply give yourself time to get your bearings in a new destination at:

  • Rental agencies sometimes offer discounts on early bookings, so reserve your ride from RFD well ahead of your flight from Juan Santamaria International Airport to Chicago. A little prep work can make a big difference in cost.

  • Chicago Rockford International Airport's street address is 2 Airport Cir.

Best time to go to Chicago

  • January is the quietest month for flights from Juan Santamaria International Airport to Chicago, while July is the busiest. Pick the ideal time to go to Chicago based on whether you like a lively atmosphere or a more laid-back vibe.

  • Lock in a Juan Santamaria International Airport to Chicago plane ticket with a departure in July to visit the city during its warmest month. You can expect temperatures to range from 16ºC (61ºF) to 28ºC (82ºF).

  • 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'd rather travel in cooler conditions.

More about Chicago

  • Start your Chicago trip off on the right foot by choosing the ideal place to stay. As soon as you've booked your flight from Juan Santamaria International Airport to Chicago, browse our range of hotels including:

  • There are so many things to see and do in this city it can be difficult to know where to begin. Art Institute of Chicago, Millennium Park and Willis Tower are top attractions which should be on any well-planned Chicago itinerary.

Explore more of the United States

  • Columbus is just one of the many places in the United States waiting to be explored once you've taken in the sights of Chicago. Around 451 kilometres away to the southeast, its best attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Around 257 kilometres southeast of Chicago, Indianapolis is another essential stop in the United States. Experience this destination's highlights firsthand at Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

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.