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Cheap flights from San José (SJO) to Chicago (CHI) from $144

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
SJO — CHI
Jun 7 — Jun 141
From?
To?
Fri 6/7
Fri 6/14
1 adult, Economy
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The best prices from San José Juan Santamaria Intl to Chicago are usually found in August or February, booked 26 days in advance, depart on a Tuesday or Thursday and return on a Wednesday

Cheap flight deals from San José to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San José (SJO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 2, 2024.

Popular in

March

Cheapest in

August

Round-trip from

$222

One-way from

$214
High demand for flights, 20% potential price rise
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Best time to find cheap flights, 34% potential price drop
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From San José Juan Santamaria Intl to Chicago (CHI)
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One-way flight from San José Juan Santamaria Intl to Chicago (CHI)
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What is the cheapest day to fly round-trip from San José, San José Province to Chicago?

Leaving on a Monday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 50% on the overall cost on flights from San José, San José Province to Chicago.

How far in advance should I book a flight from San José, San José Province to Chicago?

To save on the cost of your flight from San José, San José Province to Chicago, book at least 27 days before your planned departure. Booking around this time can save you about 81% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $420 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $534.

What is the cheapest month to fly from San José, San José Province to Chicago?

Due to multiple factors, expect to potentially pay more when booking in March. For low rates, August can be a great choice for travel to Chicago. Flights to Chicago from San José, San José Province in August are about $414 on average during August, but can be found for as low as $269.

What is the cheapest time of day to fly from SJO to CHI?

One of the essential ways to save on airfare from San José, San José Province to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 34% on airfare.

Cheap Spirit Airlines flights from San José to Chicago

Explore cheap flight options specifically provided by Spirit Airlines for the route between San José and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,807,690 searches. Data last updated June 2, 2024.
Take a look at some of the lowest-priced Spirit Airlines flights heading from San José to Chicago. Come back soon if you're not finding the exact deal you're looking for.
Tue 8/2012:55 amSJO - ORD
1 stop13h 02mSpirit Airlines
Mon 8/266:36 pmORD - SJO
2 stops17h 57mSpirit Airlines
Deal found 6/1$199
Tue 8/2012:55 amSJO - ORD
1 stop13h 02mSpirit Airlines
Mon 8/264:10 pmORD - SJO
1 stop8h 55mSpirit Airlines
Deal found 6/1$212
Wed 9/412:32 pmSJO - ORD
1 stop10h 28mSpirit Airlines
Tue 9/105:00 amORD - SJO
1 stop7h 32mSpirit Airlines
Deal found 6/1$213
Fri 8/2312:55 amSJO - ORD
1 stop13h 02mSpirit Airlines
Tue 8/274:10 pmORD - SJO
1 stop8h 55mSpirit Airlines
Deal found 6/1$219
Wed 9/1112:32 pmSJO - ORD
1 stop10h 27mSpirit Airlines
Mon 9/165:35 pmORD - SJO
1 stop18h 57mSpirit Airlines
Deal found 6/2$220
Thu 9/1212:32 pmSJO - ORD
1 stop10h 28mSpirit Airlines
Mon 9/235:00 amORD - SJO
1 stop7h 32mSpirit Airlines
Deal found 6/1$226
Mon 8/1912:55 amSJO - ORD
1 stop17h 23mSpirit Airlines
Mon 8/268:30 amORD - SJO
1 stop28h 03mSpirit Airlines
Deal found 6/1$229
Wed 9/412:32 pmSJO - ORD
1 stop10h 28mSpirit Airlines
Tue 9/105:00 amORD - SJO
1 stop7h 32mSpirit Airlines
Deal found 6/2$235
Fri 8/2312:55 amSJO - ORD
1 stop13h 02mSpirit Airlines
Tue 8/276:36 pmORD - SJO
2 stops17h 57mSpirit Airlines
Deal found 6/1$236

Cheap Avianca flights from San José to Chicago

Explore cheap flight options specifically provided by Avianca for the route between San José and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,807,690 searches. Data last updated June 2, 2024.
Have a look at some of the cheapest available Avianca flights departing from San José and landing in Chicago. Make sure to examine the flight information before completing your reservation.
Fri 6/75:45 amSJO - ORD
1 stop7h 55mAvianca
Wed 6/124:00 pmORD - SJO
1 stop6h 45mAvianca
Deal found 6/2$540
Fri 6/75:45 amSJO - ORD
1 stop7h 55mAvianca
Sun 6/94:00 pmORD - SJO
1 stop6h 45mAvianca
Deal found 6/2$650

Cheap San José to Chicago flights in June & July 2024

Find cheap flight options from San José to Chicago specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,807,690 searches. Prices were last updated on June 2, 2024.
These are some of the most attractive deals on flights from San José to Chicago in 2024. Check back soon for alternative fares.
Wed 6/2612:59 amSJO - ORD
2 stops12h 30mSpirit Airlines
Mon 7/111:02 amORD - SJO
1 stop14h 07mSpirit Airlines
Deal found 6/2$281
Wed 6/2612:59 amSJO - ORD
1 stop15h 41mSpirit Airlines
Mon 7/15:05 amORD - SJO
1 stop7h 32mSpirit Airlines
Deal found 6/2$291
Wed 6/1912:59 amSJO - ORD
1 stop14h 29mSpirit Airlines
Thu 6/275:05 amORD - SJO
1 stop7h 32mSpirit Airlines
Deal found 6/1$301
Wed 6/1912:32 pmSJO - ORD
1 stop19h 32mSpirit Airlines
Thu 6/275:18 pmORD - SJO
1 stop7h 51mSpirit Airlines
Deal found 6/1$306
Thu 6/2712:32 pmSJO - ORD
1 stop11h 23mSpirit Airlines
Sat 8/36:46 pmORD - SJO
1 stop17h 51mSpirit Airlines
Deal found 6/1$307
Wed 6/2612:59 amSJO - ORD
1 stop15h 41mSpirit Airlines
Sun 6/305:05 amORD - SJO
1 stop7h 32mSpirit Airlines
Deal found 6/1$309
Tue 6/2512:32 pmSJO - ORD
1 stop20h 29mSpirit Airlines
Tue 7/25:39 amORD - SJO
1 stop8h 06mSpirit Airlines
Deal found 6/1$310
Wed 6/2612:59 amSJO - ORD
2 stops12h 30mSpirit Airlines
Sun 6/305:05 amORD - SJO
1 stop7h 32mSpirit Airlines
Deal found 6/1$311
Tue 6/1812:59 amSJO - ORD
1 stop8h 02mSpirit Airlines
Thu 6/275:21 amORD - SJO
1 stop8h 24mSpirit Airlines
Deal found 6/2$312

San José to Chicago 2024 flight deals

Discover exclusive flight deals for travel between San José and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,807,690 searches. Data last updated June 2, 2024.
These are some of the most attractive deals on flights from San José to Chicago in 2024. Check back soon for alternative fares.
Tue 8/2012:55 amSJO - ORD
1 stop13h 02mSpirit Airlines
Mon 8/266:36 pmORD - SJO
2 stops17h 57mSpirit Airlines
Deal found 6/1$199
Tue 8/2012:55 amSJO - ORD
1 stop13h 02mSpirit Airlines
Mon 8/264:10 pmORD - SJO
1 stop8h 55mSpirit Airlines
Deal found 6/1$212
Wed 9/412:32 pmSJO - ORD
1 stop10h 28mSpirit Airlines
Tue 9/105:00 amORD - SJO
1 stop7h 32mSpirit Airlines
Deal found 6/1$213
Fri 8/2312:55 amSJO - ORD
1 stop13h 02mSpirit Airlines
Tue 8/274:10 pmORD - SJO
1 stop8h 55mSpirit Airlines
Deal found 6/1$219
Wed 9/1112:32 pmSJO - ORD
1 stop10h 27mSpirit Airlines
Mon 9/165:35 pmORD - SJO
1 stop18h 57mSpirit Airlines
Deal found 6/2$220
Thu 9/1212:32 pmSJO - ORD
1 stop10h 28mSpirit Airlines
Mon 9/235:00 amORD - SJO
1 stop7h 32mSpirit Airlines
Deal found 6/1$226
Mon 8/1912:55 amSJO - ORD
1 stop17h 23mSpirit Airlines
Mon 8/268:30 amORD - SJO
1 stop28h 03mSpirit Airlines
Deal found 6/1$229
Wed 9/412:32 pmSJO - ORD
1 stop10h 28mSpirit Airlines
Tue 9/105:00 amORD - SJO
1 stop7h 32mSpirit Airlines
Deal found 6/2$235
Fri 8/2312:55 amSJO - ORD
1 stop13h 02mSpirit Airlines
Tue 8/276:36 pmORD - SJO
2 stops17h 57mSpirit Airlines
Deal found 6/1$236

Non-stop flights to Chicago from San José

Discover non-stop flight options from San José to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,807,690 searches. Data last updated June 2, 2024.
Take a look at some of the direct flights traveling from San José to Chicago in the near future. If you're looking for other options for flights from San José to Chicago, make sure to update the search form at the top of page.
Wed 7/175:45 amSJO - ORD
Nonstop7h 55mAvianca
Wed 7/244:00 pmORD - SJO
Nonstop6h 45mAvianca
Deal found 6/2$648
Wed 8/145:45 amSJO - ORD
Nonstop7h 55mAvianca
Wed 8/214:00 pmORD - SJO
Nonstop6h 45mAvianca
Deal found 6/1$650
Wed 8/75:45 amSJO - ORD
Nonstop7h 55mAvianca
Wed 8/144:00 pmORD - SJO
Nonstop6h 45mAvianca
Deal found 6/1$694
Fri 7/125:45 amSJO - ORD
Nonstop7h 55mAvianca
Sun 8/44:00 pmORD - SJO
Nonstop6h 45mAvianca
Deal found 5/31$722
Wed 7/245:45 amSJO - ORD
Nonstop7h 55mAvianca
Sun 7/284:00 pmORD - SJO
Nonstop6h 45mAvianca
Deal found 6/1$766
Sat 7/271:00 pmSJO - ORD
Nonstop5h 28mUnited Airlines
Sat 8/37:41 amORD - SJO
Nonstop5h 14mUnited Airlines
Deal found 6/2$770
Wed 7/105:45 amSJO - ORD
Nonstop7h 55mAvianca
Wed 7/174:00 pmORD - SJO
Nonstop6h 45mAvianca
Deal found 6/2$810
Sat 7/271:00 pmSJO - ORD
Nonstop5h 28mUnited Airlines
Sat 8/37:41 amORD - SJO
Nonstop5h 14mUnited Airlines
Deal found 6/1$823
Wed 6/195:45 amSJO - ORD
Nonstop7h 55mAvianca
Sun 6/234:00 pmORD - SJO
Nonstop6h 45mAvianca
Deal found 6/1$855

San José to Chicago flights leaving soon

Find last-minute flight options from San José to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,807,690 searches. Data last updated June 2, 2024.
Consider one of these great deals we found on last-minute flights from San José to Chicago. It's wise to confirm all flight details are correct before booking.
Wed 6/1212:59 amSJO - ORD
1 stop15h 41mSpirit Airlines
Tue 6/1811:02 amORD - SJO
1 stop14h 07mSpirit Airlines
Deal found 6/2$331
Wed 6/1212:59 amSJO - ORD
1 stop14h 29mSpirit Airlines
Tue 6/185:39 amORD - SJO
2 stops19h 30mSpirit Airlines
Deal found 6/2$335
Wed 6/1212:59 amSJO - ORD
1 stop15h 41mSpirit Airlines
Tue 6/1811:02 amORD - SJO
1 stop14h 07mSpirit Airlines
Deal found 6/1$340
Wed 6/1212:59 amSJO - ORD
1 stop22h 56mSpirit Airlines
Thu 6/201:00 pmORD - SJO
2 stops48h 45mSpirit Airlines
Deal found 6/1$373
Sun 6/912:59 amSJO - ORD
1 stop22h 56mSpirit Airlines
Mon 6/175:18 pmORD - SJO
1 stop7h 51mSpirit Airlines
Deal found 6/1$374
Wed 6/1212:59 amSJO - ORD
2 stops17h 27mSpirit Airlines
Tue 6/185:18 pmORD - SJO
1 stop7h 51mSpirit Airlines
Deal found 6/1$377
Wed 6/125:45 amSJO - ORD
1 stop7h 55mMultiple Airlines
Sat 6/155:18 pmORD - SJO
1 stop7h 51mMultiple Airlines
Deal found 6/2$379
Wed 6/1212:59 amSJO - ORD
2 stops12h 30mSpirit Airlines
Tue 6/185:39 amORD - SJO
2 stops19h 30mSpirit Airlines
Deal found 6/2$392
Sun 6/912:59 amSJO - ORD
1 stop14h 29mSpirit Airlines
Mon 6/171:23 pmORD - SJO
2 stops24h 22mSpirit Airlines
Deal found 6/1$398

One-way flights to Chicago from San José

Search for one-way flight options from San José to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,807,690 searches. Data last updated June 2, 2024.
If you're seeking multiple options on one-way flights from San José to Chicago, be sure to check out these deals, which are updated often. Users in need of a round-trip flight from San José to Chicago instead should update the search form at the top of page.
Mon 8/261:41 pmSJO - ORD
2 stops21h 22mSpirit Airlines
Deal found 6/1$144
Sun 8/251:41 pmSJO - ORD
2 stops33h 24mSpirit Airlines
Deal found 6/1$169
Mon 8/2612:29 pmSJO - ORD
1 stop26h 28mSpirit Airlines
Deal found 6/1$171
Thu 6/139:19 amSJO - MDW
1 stop28h 15mFrontier
Deal found 6/1$178
Tue 6/1812:59 amSJO - ORD
2 stops18h 48mSpirit Airlines
Deal found 5/31$181
Sat 10/1912:32 pmSJO - ORD
1 stop10h 28mSpirit Airlines
Deal found 6/1$183
Tue 6/1812:59 amSJO - ORD
3 stops18h 48mSpirit Airlines
Deal found 6/2$186
Wed 6/1912:59 amSJO - ORD
1 stop8h 02mSpirit Airlines
Deal found 6/1$187
Fri 7/1912:55 amSJO - ORD
1 stop14h 35mSpirit Airlines
Deal found 6/1$188

Find flights from San José to Chicago within your budget

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, Cheapflights users made 2,807,690 searches. Data last updated June 2, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$199 - $668

Route

Depart

Return

Price

San José Juan Santamaria IntlChicago O'Hare Intl

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 8/20

1 stop13h 02m

Chicago O'Hare Intl

Mon 8/26

2 stops17h 57m

$199

San José Juan Santamaria IntlChicago O'Hare Intl

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 8/20

1 stop13h 02m

Chicago O'Hare Intl

Mon 8/26

1 stop8h 55m

$212

San José Juan Santamaria IntlChicago O'Hare Intl

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 9/4

1 stop10h 28m

Chicago O'Hare Intl

Tue 9/10

1 stop7h 32m

$213

San José Juan Santamaria IntlChicago O'Hare Intl

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 8/23

1 stop13h 02m

Chicago O'Hare Intl

Tue 8/27

1 stop8h 55m

$219

San José Juan Santamaria IntlChicago O'Hare Intl

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 9/11

1 stop10h 27m

Chicago O'Hare Intl

Mon 9/16

1 stop18h 57m

$220

San José Juan Santamaria IntlChicago O'Hare Intl

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 9/12

1 stop10h 28m

Chicago O'Hare Intl

Mon 9/23

1 stop7h 32m

$226

San José Juan Santamaria IntlChicago O'Hare Intl

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 9/4

2 stops34h 21m

Chicago O'Hare Intl

Tue 9/10

2 stops16h 48m

$284

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 8/25

1 stop10h 09m

Chicago Midway

Sat 8/31

1 stop27h 25m

$464

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 10/7

1 stop7h 31m

Chicago Midway

Sat 10/19

1 stop6h 53m

$668

Flights are sorted by cheapest first

Deals found on 6/1

How far ahead should I book a flight from San José, San José Province to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from San José to Chicago. Price data was last updated on May 31, 2024.
The price you pay for your flight from San José, San José Province to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 26 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Search Deals

What is the cheapest day to fly from San José, San José Province to Chicago?

Use this chart to determine the cheapest time to fly round-trip from San José to Chicago. Price data was last updated on May 26, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their San José, San José Province to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Best time to book a flight from San José to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San José with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 2, 2024.
Peruse reviews from past customers who have flown with Spirit Airlines, Avianca and United Airlines from San José to Chicago to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.1
Very good
9,197 reviews
Check prices

Overall

8.1

Entertainment

7.3

Comfort

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

Alaska Airlines
8.1
Very good
9,197 reviews
Alaska Airlines
8.1
Very good
9,197 reviews
Check prices

Overall

8.1

Entertainment

7.3

Comfort

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

Delta
8.0
Very good
10,402 reviews
Alaska Airlines
8.1
Very good
9,197 reviews
Check prices

Overall

8.1

Entertainment

7.3

Comfort

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

Copa Airlines
8.0
Very good
2,599 reviews
Alaska Airlines
8.1
Very good
9,197 reviews
Check prices

Overall

8.1

Entertainment

7.3

Comfort

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

Aeromexico
7.6
Good
2,473 reviews
Alaska Airlines
8.1
Very good
9,197 reviews
Check prices

Overall

8.1

Entertainment

7.3

Comfort

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

Avianca
7.5
Good
3,626 reviews
Alaska Airlines
8.1
Very good
9,197 reviews
Check prices

Overall

8.1

Entertainment

7.3

Comfort

7.9

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

Related info for your journey

Find useful and relevant information for your journey from San José to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San José to Chicago?

    Located just 8.8 mi from the city center, San José Juan Santamaria Intl is the airport most travelers will use when flying to Chicago from San José. Booking flights from Juan Santamaria Intl (SJO) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 7 different airlines.

  • Can I find flights from San José, San José Province to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from San José, San José Province to Chicago for under $200. The cheapest flight booked recently is on Spirit Airlines for just $199, but on average you can expect to pay $234.

  • Are there nonstop flights from San José, San José Province to Chicago for under $700 on Cheapflights?

    Cheapflights has at least 12 direct flights from San José, San José Province to Chicago under $700. A good price for a nonstop flight from San José, San José Province to Chicago is less than $798.

  • Are there last-minute flights available from San José, San José Province to Chicago for under $400?

    There are currently 20+ open flights from San José, San José Province to Chicago within the next 7 days for less than $400.

  • What is the cheapest airline to fly from San José, San José Province to Chicago round-trip?

    Cheapflights users have booked flights from San José, San José Province to Chicago round-trip from $199. Spirit Airlines is 51% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest flights from San José, San José Province to Chicago?

    On average you can expect to pay $362 for a flight from San José, San José Province to Chicago. The cheapest flight overall is $195 while the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl) is currently priced at $202.

  • What does SJO to ORD mean?

    Great question - SJO to ORD just means San José Juan Santamaria Intl Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from San José to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your San José to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from San José to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter San José to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from San José to Chicago that include hotel bookings?

    Yes. In addition to deals on San José to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San José to Chicago?

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

  • Can I find deals for business class flights from San José to Chicago?

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

  • Can I find deals for flights from San José to Chicago that allow pets onboard?

    Many airlines flying from San José to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from San José to Chicago?

    Yes, you can often find last-minute deals on San José to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the San José, San José Province to Chicago flight deals updated?

    The San José, San José Province to Chicago flight deals you see on this page were last updated on 6/2.

  • What are the most popular airlines that fly from San José, San José Province to Chicago?

    Before booking your flight from San José, San José Province to Chicago check out the most popular airlines for this route: American Airlines, Aeromexico or Avianca.

  • What is the cheapest month to book a flight from San José, San José Province to Chicago?

    Currently, February is the cheapest month in which you can book a flight from San José, San José Province to Chicago (average of $244). Flying from San José, San José Province to Chicago in July is currently the most expensive (average of $324). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for San José to Chicago
See prices for flight routes from nearby airports that may be better suited for you.

San José to O'Hare Intl flights
San José to Midway flights
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Top 7 airlines flying from San José to Chicago

Discover the top 7 airlines that operate flights from San José to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,807,690 searches. Data last updated June 2, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$212Average$368FlexibilityNo cancel feeOn-time65%
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AviancaCheapest$262Average$363FlexibilityNo cancel feeOn-time71%
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JetBlueCheapest$283Average$522FlexibilityNo cancel feeOn-time62%
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Copa AirlinesCheapest$404Average$612FlexibilityNo cancel feeOn-time70%
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American AirlinesCheapest$576Average$729FlexibilityNo cancel feeOn-time71%
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AeromexicoCheapest$580Average$647FlexibilityNo cancel feeOn-timeN/A
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United AirlinesCheapest$644Average$776FlexibilityNo cancel feeOn-time69%
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Search flights from San José to Chicago by cabin class

Find flights from San José to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Hourly flight availability from San José to Chicago

Find hourly flight availability from San José to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 2, 2024.
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Weekly flight availability from San José to Chicago

Explore weekly flight availability from San José to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 2, 2024.
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Fly with Cheapflights

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How does Cheapflights help users find flights from San José to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from San José to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from San José to Chicago?

Cheapflights simply makes it quick and affordable to book flights from San José to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from San José to Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from San José to Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from San José to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from San José today and book when prices fit your budget.

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