ORD - SJO

$155 Find Cheap Flights from Chicago O'Hare Airport to San José

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to San José departing on 9/8. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to San José

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José.
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Everything you should know

Cheapest round-trip
$465
Typical prices: $390-$560
JetBlue
Fri 8/21Fri 8/28
ORD - SJO • 1 stop
Cheapest non-stop
$767
Typical prices: $558-$625
United Airlines
Sat 7/4Sat 7/11
ORD - SJO • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American Main Cabin Extra adds early boarding and drinks on this longer flight.
United Premier Access speeds check-in and boarding; arrive early at ORD security.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
Sat
You can fly direct with United Airlines. Average duration is 5h 19m
Direct flights
Direct flights
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Direct flights
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Top airlines
Cheapest • from $465 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Top layover airports
Cheapest • Avg $380 (round-trip)
Shortest trip • 6h 57m (one-way)
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 86% on-time
Best time • Fewest delays
Insights
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Insights
When to travel
Cheapest • 31% price drop
Most popular
Good to know
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San José!
Flight Deals
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Flight Deals

Cheap Flights from O'Hare Intl to San José (ORD-SJO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to San José that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to San José

Fri, Aug 21 - Fri, Aug 28
JetBlue Logo
7:00 am - 12:57 pm
ORD
-
SJO
6h 57m
1 stop
JetBlue Logo
2:02 pm - 11:44 pm
SJO
-
ORD
8h 42m
1 stop
$465JetBlue
Fri, Aug 21 - Fri, Aug 28
JetBlue Logo
7:00 am - 12:57 pm
ORD
-
SJO
6h 57m
1 stop
JetBlue Logo
2:02 pm - 11:44 pm
SJO
-
ORD
8h 42m
1 stop
$470JetBlue
Tue, Sep 8 - Sat, Sep 19
JetBlue Logo
7:00 am - 12:57 pm
ORD
-
SJO
6h 57m
1 stop
JetBlue Logo
1:05 pm - 11:31 pm
SJO
-
ORD
9h 26m
1 stop
$475JetBlue
Sun, Sep 13 - Fri, Sep 18
JetBlue Logo
6:00 am - 11:56 am
ORD
-
SJO
6h 56m
1 stop
JetBlue Logo
1:05 pm - 11:31 pm
SJO
-
ORD
9h 26m
1 stop
$479JetBlue
Thu, Oct 8 - Sun, Oct 11
Multiple Airlines Logo
1:49 pm - 11:59 pm
ORD
-
SJO
11h 10m
1 stop
Multiple Airlines Logo
4:15 pm - 12:09 pm
SJO
-
ORD
18h 54m
1 stop
$481Multiple Airlines
Thu, Oct 8 - Thu, Oct 15
Multiple Airlines Logo
1:49 pm - 11:59 pm
ORD
-
SJO
11h 10m
1 stop
Multiple Airlines Logo
4:15 pm - 12:09 pm
SJO
-
ORD
18h 54m
1 stop
$482Multiple Airlines
Sat, Aug 8 - Thu, Aug 13
Frontier Logo
5:13 pm - 8:20 am
ORD
-
SJO
16h 07m
1 stop
Frontier Logo
9:35 am - 11:10 pm
SJO
-
ORD
12h 35m
1 stop
$488Frontier
Wed, Jul 22 - Mon, Aug 3
Copa Airlines Logo
3:21 pm - 8:21 am
ORD
-
SJO
18h 00m
1 stop
Copa Airlines Logo
10:03 am - 1:02 am
SJO
-
ORD
13h 59m
1 stop
$490Copa Airlines
Thu, Oct 29 - Sat, Oct 31
United Airlines Logo
7:45 am - 7:39 pm
ORD
-
SJO
12h 54m
1 stop
United Airlines Logo
1:05 pm - 7:35 pm
SJO
-
ORD
5h 30mnonstop
$492United Airlines
Mon, Oct 26 - Mon, Nov 9
JetBlue Logo
7:00 am - 12:59 pm
ORD
-
SJO
6h 59m
1 stop
JetBlue Logo
3:05 pm - 11:44 pm
SJO
-
ORD
8h 39m
1 stop
$497JetBlue
Booking Insights

KAYAK's insights & trends for O'Hare Intl to San José flights

Get data-powered insights and trends into flights from O'Hare Intl to San José to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago O'Hare Intl Airport to San José?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to San José departing in August.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to San José?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to San José clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to San José on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago O'Hare Airport to San José. For your return ticket, we recommend flying on a Tuesday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to San José, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to San José is October, where tickets cost $361 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $669 and $606 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to San José, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to San José, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Expert advice

Expert advice for your flight from O'Hare Intl to San José

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Mark Chesnut

Mark Chesnut

Expert on SJO

Mark Chesnut is a travel writer and public speaker with more than 30 years of experience. The 2019 winner of the NLGJA Excellence in Travel Writing Award, Mark is the author of the book “Prepare for Departure” and has covered air travel for multiple top consumer and trade media outlets.

Good to know

Low seasonSeptember
Cheapest flight$155
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 26% increase in price.
Flight from Chicago O'Hare Airport to San José

When to book flights from O'Hare Intl to San José

Are your dates flexible? Find out the best times to travel from O'Hare Intl to San José based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago O'Hare Airport to San José flights

  • What is the luggage allowance on Aeromexico flights from Chicago O'Hare Airport to San José?

    For flights from Chicago O'Hare Airport to San José with Aeromexico, the maximum weight allowance is 55 pounds for all regular and Premiere fares and the maximum linear dimension limit is 62 inches. Passengers may bring one carry-on bag of up to 22 lbs plus one personal item. Fees apply for oversize and overweight luggage and will depend on the fare type and flight route.

  • How do I get from San Jose Airport (SJO) to the city center?

    The bus is the most affordable way to get to the city center. The bus stop is located just outside the airport terminal. Take the Alajuela-San Jose bus and get off at the last stop, which is in the center of San Jose. The trip takes around 45 minutes. Taxis are also available at the airport and can bring you directly to your destination in the city center.

  • What seat selection options are available on Avianca flights from Chicago O'Hare Airport to San José?

    Avianca offers various seat selection options on flights from Chicago O'Hare Airport to San José. Passengers can choose seats from the available standard seating options at no additional cost during the check-in process. Avianca also offers preferred seats for an additional fee. These seats are typically located in the front rows of the cabin or have extra legroom.

  • What services are offered by Copa Airlines to economy class passengers on flights from Chicago O'Hare Airport to San Jose?

    Copa Airlines offers a variety of services to economy class passengers on its flights from Chicago O'Hare Airport to San José. Economy class passengers can enjoy Copa Airlines' in-flight entertainment system, which includes movies, TV shows, and music. Passengers in economy class also receive complimentary meals and drinks on all Copa Airlines flights.

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

    In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to San José was $155 for a one-way ticket and $465 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and San José?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago O'Hare Airport and on arrival in San José.

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to San José?

    American Airlines, Delta, and Alaska Airlines offer inflight Wi-Fi service on the Chicago O'Hare Airport to San José flight route.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to San José?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago O'Hare Airport to San José flight route.

  • Which airline alliances offer flights from Chicago O'Hare Airport to San José?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Chicago O'Hare Airport and San José, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Chicago O'Hare Airport to San José?

    You can catch a nonstop flight from Chicago O'Hare Airport to San José on Saturday.

  • Which is the best airline for flights from Chicago to San José, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to San José are Southwest and Delta. With an average price for the route of $484 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $482 and an overall rating of 7.8.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to San José?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport to San José.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to San José?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San José from Chicago O'Hare Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to San José?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San José with an airline and back to Chicago O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and SJO can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to San José?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San José from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to San José

  • Looking for a cheap flight? 25% of our users found flights on this route for $607 or less round-trip.
  • US citizens require a valid visa to enter Costa Rica, including for flights from Chicago O'Hare International Airport (ORD) to San José (SJO). The type of visa needed depends on the purpose of travel, and there are several options such as tourist visas, work visas, and student visas.
  • Spirit Airlines assists passengers who require a wheelchair to get to and from their gate or assistance in boarding and disembarking the aircraft. The airline also offers special seating options for passengers with reduced mobility on flights from Chicago O'Hare Airport to San José, including seats with movable armrests and bulkhead seats.
  • Air Canada allows pets to travel in the cabin or as checked baggage on flights from Chicago O'Hare Airport to San José. For pets traveling in the cabin, only dogs and cats are permitted and the pet carrier will count as one of the traveler's carry-on items. For pets traveling as checked baggage, Air Canada only accepts cats and dogs, and they must be at least 12 weeks old.
  • JetBlue offers early boarding for families with children under the age of 2 and one accompanying adult on flights from Chicago O'Hare Airport to San José. This allows families to get settled on the plane before other passengers.
  • Frontier Airlines operates flights from Chicago O'Hare Airport to San José with fuel-efficient aircraft equipped with advanced technology and optimized performance capabilities to reduce carbon emissions.

Prefer to fly direct from Chicago O'Hare Airport to San José?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl to San José Juan Santamaria Intl.
Find which airlines fly direct from Chicago O'Hare Intl Airport to San José Juan Santamaria Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to San José Juan Santamaria Intl

Saturday

United Airlines

United Airlines

See more direct flights

Direct returns

San José Juan Santamaria Intl to Chicago O'Hare Intl

Saturday

United Airlines

United Airlines

See more direct flights

Reviews of the top 5 airlines serving from O'Hare Intl to San José

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San José. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to San José? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4239 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

4.0 OkaySteven, Jun 2026
ONT - LAS
Read more Southwest reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I had to run from the end of terminal one to the end of terminal two to make the connecting flight....probably a kilometer. No electric carts were available. I'm 76 and literally had to run to make the connection at the last minute. The connecting time was absolutely unrealistic. When Last Call was announced, I tried to get other Copa gate staff to call Gate 221 to let them know I was on my way, but they said no. I came within 1 minute of missing the flight.

Entire experience from check in to landing was amazing the flight crew was excellent and friendly. Seats were comfortable.

Avoid at all costs. My wife had to stay back on a connecting flight as her parents flight was delayed. 10 days later on the way back they cancelled all our flights. We had to rebook all four of us on the next days flight.

Copa staff at PTY and one particular crew member were unhelpful & rude.

Seats were awful. Media should have been included for such a long flight.

A lot things happened in this trip.The fly should be less stress.

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane

I liked the meatloaf the chicken was awful but the plane was on time and got there and the staff was nice.

Boarding was quick & efficient; they gave boarding groups due priority; staff & air crew were very cordial and helpful, pleasant flight.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Seats are absolutely not comfortable and large enough. There’s a limit and you stepped over it. I understand that there’s a business class, however for the price it costs, it’s just plain stupid for a 50 minute flight.

They should provide water to passengers who ask for it

The worst experience I've ever had because the "people" @ Avianca wouldn't let me fly because they said I needed a round trip ticket

Seating was tight. Seats don't recline. Initial flight was cancelled. Lost two days of vacation.

It was delayed and I lost my connection flight to Cali and I missed my Mom's funeral

I actually upgraded to the medium level of seats from basic and even doing that it may have been physically the most uncomfortable flight I have ever had. They packed everyone like is a train to death camp. It was a red eye so I hoped to get some sleep but it was physically impossible to find a comfortable way to rest. I met other folks on the same flight and they said the same thing. It was an utterly miserable flight and if I have any other options I will never fly with them again

Deplaning was a mess, I sat in business (seats are horrible) and the front door had a problem so we had to deplane from the rear exit. The stairs were not tall enough to reach so there was a large step down from the plane to the top of the stairs.

Staff are the rudest in the industry … awful customer service … will never fly Avianca again

Pros: we leave and arrive on time Cons: the most uncomfortable seats ever. You cant recline at all your seats. No entertainment No TVs flight attendants didn't provide even a glass of water. You have to go to back of the airplane and ask for one. I am Colombian and I remember seeing the flight attendants very neat, elegants which is or was a staple of Avianca.it was one with tennis shoes, no male up, the hair was messy... that was really odd.

Here we have another airline flying to Guatemala but doesn't have a plus or a less, just in the middle. Why? Well, first we don't have even free water Movie selection is poor Seats don't recline in some places Food selection is carb based Forgot to mention, customer service on the web is the worst. Good things; Very reliable on schedule Kind crew

Everything you need to know for your flight from O'Hare Intl to San José

Information on your arrival and departure airports