Use The Flight Search Form To:
- get the price graph for the next days, weeks and months
- narrow flight results by the time of the day of departure/arrival
- narrow flight results by price range and preferred airlines
- for indirect flights, search by stopover airport
- compare live prices for the same flight by multiple vendors
- find much more flights to than listed below
Find Cheap Flights From Chicago To San Jose
Airports in Chicago
The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use Orbitz.com to find flights from both O’Hare and Midway. O’Hare International Airport is located approximately 17 miles northwest of downtown Chicago. Midway International Airport is located on the city’s southwest side, approximately eight miles from Chicago’s Loop. O’Hare serves as a hub for American Airlines and United Airlines, and Midway is a hub for Southwest Airlines.
Chicago Airport Parking
Daily, hourly, and valet parking are available at O’Hare. Rates vary from $2.00 to $10.00 per hour. An economy parking lot is also available at a rate of $2.00 per hour. Similar parking options and rates apply at Midway.
Chicago Airport Transportation
There are numerous transportation options for getting to and from both O’Hare and Midway. O’Hare can be accessed via regional trains, buses, and local mass transit lines. The CTA Blue Line offers a fast and convenient transportation option to and from this airport. Midway is served by the CTA Orange Line. Car rental services are available at both airports, and travelers can quickly book car rental services at either airport using Orbitz.com.
Chicago Airport Restaurants
San Jose Airport Information
Ground Transportation in San Jose
San Jose Weather Information
What to Do in San Jose
San Jose To Chicago Flight Schedule
Scan through flights from Juan Santamaria International Airport to O’Hare International Airport for the upcoming week. Sort the list by any column, and click on a dollar sign to see the latest prices available for each flight.
Flights.com only offers pricing for airlines that display a check fare on the days of the week each flight is available. A dot indicates a flight is scheduled, but online booking is not currently available.
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Another Approach Pay Up
Actually finding fantastic fares is usually a matter of luck and its clear from the recommendations above that finding a good fare that meets your other criteria requires effort.
The difference between average, good and great prices usually isnt much more than $100 and sometimes searching, researching and waiting backfires with rising fares.
Especially if your vacation dates are set it may not be worth your time and effort to bargain hunt. Just check the price ranges below and the fares you find are in the reasonable range buy tickets and dont look back.
Airports Fact And Comparison

Chicago Ohare International ORD
Chicago Ohare International is the largest airport in United States. You can fly to 262 destinations with 49 airlines in scheduled passenger traffic.
Destinations from Chicago Ohare International
Juan Santamaria International SJO
Juan Santamaria International is the largest airport in Costa Rica and is based in San Jose. You can fly to 47 destinations with 29 airlines in scheduled passenger traffic.
Destinations from Juan Santamaria International
Are you still looking for a good deal?
We can help you find the best price on this route!
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Tips & Tricks On Customs Immigration
So, youve followed this guide and found some great flight tickets to Costa Rica from the city of your choice with the airline of your choice. You have a great direct connection at a decent price, midweek, with little stress. All you have to do now is show up to the airport, check in, board, take off, travel, and arrive. Now what?
Here, well talk about what you can expect when on a flight to Costa Rica, especially now the Covid-19 pandemic has changed travel for the foreseeable future. Then well walk you through the arrival process, getting you through immigration and customs, and out of the airport to enjoy your vacation.
Unlike many other countries, at this time, Costa Rica doesnt require a Covid-19 test to enter.
You dont need to worry about that at all, but if that ever changes, well keep you updated. What you do need to do, however, is fill out an online Health Pass, one for every traveler in your group. You have to do this within 72 hours of your arrival in Costa Rica. Health passes filled out more than 72 hours before arrival will not be accepted.
Once youve filled out the online health pass, itll generate an automatic QR code that will display on your phone for Immigration to check upon arrival in Costa Rica.
Another factor of traveling to Costa Rica right now is the mandatory travel insurance.
Your insurance policy must be uploaded to the online Health Pass you fill in.
So thats the covid travel part out of the way. What else?
Connecting Flights Vs Direct Flights From Chicago To Tamarindo
Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.
The average price for connecting flights from Chicago to Tamarindo is not available.
The average price for direct flights from Chicago to Tamarindo is $631.
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Flights To Costa Rica: The Ultimate Guide
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Now youve seen how great a vacation to Costa Rica will be, its time to look at some logistics. The most important logistic, of course, is getting to Costa Rica. Whats the best way to get here anyway? For most of you, getting to Costa Rica means flying to Costa Rica. And we have you covered with all aspects of that in our Ultimate Guide to Costa Rica Flights.
Whether youre looking for the cheapest flights to Costa Rica or the quickest, most convenient way to get to the Land of Pura Vida, we can help inform you. We hope the info on this page will get your vacation juices flowing with the knowledge that finding airfare to Costa Rica that suits your schedule and budget is now easier than ever. Lets get started.
So Now Lets Double Down Further On This And Look At Some Direct Nonstop Routes To San Jose Costa Rica
San Jose is the biggest and busiest out of the two international airports in Costa Rica. It serves the capital city of San Jose, although its located outside of town in Alajuela. In this section of our Ultimate Guide to Flying to Costa Rica, we wanted to highlight what weve already mentioned above, but this time show you clearly what exact direct routes fly into San Jose.
From the United States, you can fly directly into San Jose from the following cities:
- Atlanta
- San Salvador
- Zurich
Looks a little thin on the ground, doesnt it? Thats because, for now, were keeping London and various Canadian cities out of the list because theyre not operating flights to Costa Rica at the moment.
We hope, though, to add more cities to this list soon. Indeed, according to Avianca, flights from Cali, Medellin, and Managua are on their way. Now lets look at Guanacaste Airport.
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What Are The Cheapest Flights From Chicago To Costa Rica
While on average a flight from Chicago to Costa Rica is generally $517, our data shows the cheapest flight currently is $90. When looking at the most popular route, , you can expect to pay $201 for that flight.
Related searches
Visitors from Chicago are not required to quarantine after entering Costa Rica.DocumentsEpidemiological Health Pass Form – The Health Pass can only be completed within 72 hours of arriving in the country. One form must be completed per person, including minors, without exception.Health Insurance – Tourists may get an insurance from Costa Rican insurance companies that are registered and authorized by the General Superintendence of Insurance of Costa Rica.
When Are Tickets Cheapest
Once upon a time, before the internet, you used to use a travel agent to buy flights, or go directly through the airline. Youd give them a call or head down to their office and theyd hook up your flights for you through a computerized reservation system.
If you were in the office, the agent would sit on one side of a desk, and you another. Theyd have access to airline, flight numbers, and airlines on their screens and give you some options. Prices would be similar, although they might vary depending on the airline. Youd then choose your flight, pay for it, and then come back in a few days to pick up your tickets . There was no real way of determining when tickets would be cheaper or not.
Theres a reason for the history lesson. Its to point out how things used to be compared to how they are now. Nowadays, its all changed. Airline ticket prices vary on a whim, and things can get confusing when youre looking for a flight deal.
Going forward, well assume you dont have air miles, or belong to any individual airlines reward program. Well also assume youre not traveling standby or working for an airline. This is all about finding the cheapest airfare to Costa Rica as a regular travel with no perks in front of you at all.
Those of you with air miles, though, should know the value of your miles changes depending on the time of year. The busier travel times we talk about below can mean your miles drop slightly in value. Check with your airline.
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Private Charter Flights To Costa Rica
It might not be the most ecologically sound way to get to Costa Rica, but its certainly the most comfortable. And if youre in a large enough group, it might not even be as expensive as you think, either. Yes, if youre so inclined, you can certainly travel to Costa Rica on a private flight. And your last name doesnt need to be Kardashian to do so, either.
In this section, were going to talk a little about chartering a private plane, rather than buying one. If youre interested in buying your own private jet or already have one, theres not much advice we can give you on this page other than which Costa Rican airport to fly into . Outside of that, it should be us asking you for advice rather than the other way round!
But if youre considering chartering a private plane, we can offer you some information about flying to Costa Rica.
First, though, why would you hire a private flight in the first place?
Weve already seen theres a lot of airlines flying in and out of Costa Rica nowadays, from all over the world. What are the advantages of going private?
You know all this already, of course. Everyone knows the benefits of flying private, even if most people have never had the pleasure of doing so. What you really want to know is the price, right?
How much does it cost for a private charter flight to Costa Rica?
When considering these factors, you also need to consider the range of your plane . Smaller planes have lower ranges, while larger planes can fly further.
The Southwest Travel Experience

You’ll deplane 12 miles west of downtown San Jose, CR, when you arrive at Juan Santamaria International Airport.
At Southwest, we know it takes more than great deals on San Jose, Costa Rica, airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Chicago to San Jose, Costa Rica, the best it can be. Learn more about the Southwest® travel experience before you book your flight from Chicago Midway International Airport to Juan Santamaria International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to San Jose, Costa Rica, know that you wont be surprised at checkout. Low fares and no hidden fees. That’s Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? from us. Book your flight today and know that you’ll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
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Where To Buy Cheap Flights From Chicago To Tamarindo
The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don’t have to – which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Chicago to Tamarindo based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you’d like to learn more, read our article about the best time to buy airline tickets.
There Are A Lot Of Reasons To Book Your Flights To San Jose Sjo From Chicago Ord With American Airlines On Travelocity
At Travelocity our vast and up-to-the-minute inventory puts all of our best flight deals in one place. So, whether youre traveling on business or jetting off with friends and family, you can trust Travelocity to get you there.
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Browsing History Location & Other Information May Target You For Higher Prices
The same search done at the same time by different people using different computers in different places may result in different prices its called dynamic pricing.
Frommers recently published an article noting that searches from computers located in affluent zip codes resulted in higher priced hotel rooms on some of the major travel websites.
This isnt a new phenomenon and may apply to airfare as well. In 2012 the Wall Street Journal found that Orbitz increased travel prices by 30% for Mac users. However, in 2017 and 2018 the White House issued executive orders significantly reduceding individuals rights to protect their information in the U.S. and allowed internet service providers to offer personal data for sale on the open market.
Cookies, browsing history, the content of e-mails, credit card bills, credit history and dozens of other data sets may be used to determine your personal dynamic price for nearly anything.
That should be illegal! is a common response to the idea that this data is used not only to target potential customers for specific advertising but also to steer them through search and shopping processes towards decisions that maximize profit.
Searching from a library computer, Virtual Private Networks , private browsing, clearing cookies and history can hide some of the data used against you.