Find cheap flights from Chicago Midway Airport to Costa Rica

Find cheap flights from Chicago Midway Airport to Costa Rica

Round-trip
Economy
Chicago (MDW)
Costa Rica
Tue 12/1
Tue 12/8
Any month
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Good to know

Low season

April Best time to beat the crowds with an average 10% drop in price.

High season

December Most popular time to fly with an average 9% increase in price.

Average price round-trip

$690 (avg. price over the last 2 weeks)

Good deal round-trip

$398 or less

Top tips for finding cheap flights to Costa Rica

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly to Costa Rica is August.
  • Morning departure is around 7% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Costa Rica flights

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Top 3 airlines serving Chicago Midway to Costa Rica

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,799 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Great crew members. Very friendly and helpful."

Cons: "No mechanical failures or delays would be nice"

Cons: "I had a tight connection, but made it to the gate in time. I walked down the jetway to what appeared to be a locked door, with no one there to guide me on how to board. It turns out there was a stairwell at the end of the jetway, which was to take me to a bus on the tarmac. This was very stressful."

Cons: "uncomfortable seats, thin seat cushions"

Pros: "very nice crew"

Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."

Pros: "Just fine, beverage service was friendly."
Cons: "The entertainment system was out the entire flight. The flight attendants were just talking to each other as we left, even when I tried to say thank you."

Pros: "The crew was amazing"
Cons: "Don’t change my chosen seat that I paid for as I am entering the plane without my knowledge and acceptance"

Pros: "The entire thing, food, service, and ..."
Cons: "More room in each seat"

Pros: "Great flight"

Cons: "If there could have been some sort of service at DTW to take customers to the gate of their connecting flight, for cases of really short time window of course, it’d be extremely helpful."

Pros: "Staff from Check in to aircraft very pleasant. Snack choice in Coach impressive."

Pros: "Nothing"
Cons: "The flight was not comfortable and shaking as if it is about to explode"

Cons: "At least one hour late"

Pros: "Cabin crew were very good. Very pleasant."
Cons: "Unpacking wet clothes from one of my bags. It must have been left out in the rain for some time. I filed a separate complaint with Delta."

Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."

Pros: "Short flight"
Cons: "Flight attendant was not willing to go above and beyond as he stated he would. My husband asked for a coke and the flight attendant told him he could only get water."

Pros: "Food and service was amazing."

Pros: "Hot towel was a plus"
Cons: "The seats weren't that comfortable"

Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."

Cons: "When my flight with American Airlines cancelled, I felt so panicked because I needed to be in Florida on Saturday night. But thankfully, lady who works for American Airlines solved my problem on the phone in couple of minutes easily. After that, when we were boarding to the aircraft, there was a cabin attendant lady. She came to us and ask me and my mother if we can talk English.I answered her with yes we can, but she demands to talk with my mother. And English is not her native language, but it doesn't prove that she doesn't know it. She tried to ask questions to her like, "where were you today?" so we couldn't really understand the reason for her to ask those questions in the first place. So we couldn't really say anything. While we were talking about my mother's English, the all aircraft was watching us, and trying to figure out what was going on. After all, she made us to sit there and wait her to replace us with other passengers. We waited the whole aircraft to be seated, then she took us to another seat with my mother. I can understand that it is her job but I'm not sure, if it had to be that much discomfort. We got pretty upset about it and it affects our flight quality. Plus, while cabin crew serving beverages, they didn't really ask us anything. We needed to call them for our order. To be honest, I would never flight with Delta. It was a disappointment."

Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"

Pros: "Flight attendant was great!"

Pros: "Easy to boar, no delay and arrived on time"
Cons: "One of the flight attendant was a little rude to some passengers."

Pros: "No issues boarding as a group of 6, including one child. We all had at least a personal item and/or a carry-on to stow. The flight was easy, comfortable, and the free movies were current and definitely helped pass the time."
Cons: "We were seated right behind the delta comfort+ and saw the special snacks they got. Being teased by that is not a huge deal, just a little disappointed by the regular snack selection, the snack mix was definitely subpar."

Pros: "Getting home in one piece"
Cons: "Why do airlines schedule 2 flights for the exact same time in the exact same gate? Just to watch passengers squeeze in like cattle??"

Pros: "Crew member Lori was exceptional. Great detail to safety and customer service!"

Pros: "Landed from Sydney at 8am. Flew to San Francisco at 4pm. Long wait. Not good."
Cons: "Landed in Los Angeles at 8am. Left for San Francisco at 4pm. Aweful."

Pros: "We didn’t order food"

Pros: "I liked the plane being on time & a smooth flight. The crew was great too."
Cons: "N/A"

Pros: "The crew was fantastic. I generally love flying Delta and find their crew to always be very professional and kind."
Cons: "As this was a smaller, regional jet, there weren't a lot of amenities. But that's fine, it's only a 40-minute flight!"

Pros: "The USB connection at my seat worked; it often does not, so this was an improvement. The turkey sandwich was moist and delicious."

Pros: "First flight"
Cons: "Too packed"

Pros: "The staff and crew were so helpful and friendly! Stress free flight."
Cons: "Nothing"

Pros: "The flight crew were really nice and I was really comfortable in the Comfort+ section of the plane. It's a nice upgrade for Delta and hope the other airlines follow suit. Granted I had a very active infant, I didn't have any problems."

Cons: "They should provide good hindi movies and songs in the flight"

Cons: "The flight crew and staff were all great!"

Pros: "It was only 1.5 hr flight."
Cons: "Apparently Delta has decided even if you have a qualified KTN, they can arbitrary decide not to honor do you cannot precheck thru TSA. No way to input KTN at purchase on website and couldn't get it done at ticket counter. Thanks Delta"

Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."

Pros: "On time, efficient boarding, no lines or delays. Attendants not as top notch as on the domestic leg but we're friendly and efficient. Loved the seat back entertainment options, watched a movie, listened to 2 podcasts, and enjoyed some excellent blues music. All while tracking he flight progress. Made the 6 hour flight go by quickly and not mind the bumpy air in the tropics."

Pros: "The crew friendly,boarding was easy the flight was comfortable they even went around and gave blankets they could do a little more with the snacks. There were TVs so the entertainment was really good. Seats didn't go back, wish they did."
Cons: "I wish they had more snacks like JetBlue but all was fine."

Cons: "Access to LGA has become too problematic due to the construction. We will use other airports on our future trips to NY"

Pros: "When you are delayed, there is not much to commend."
Cons: "Delayed. That pretty well says it all."

Pros: "The staff was friendly and curtious"

Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."

Pros: "Movies- pro staff"

Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."

Pros: "Everything was great from the check in process to the de-planing in Detroit. When we checked in at SLC the agent used my last name, which showed me the extra mile Delta staff will go to make the travel with them professional and curious. The flight left on time and when we arrived in Detroit our bags were already there waiting for us. Couldn't have asked for more!"
Cons: "Nothing at all"

Cons: "I had a reserved Comfort Class Aisle seat, purchased at time of reservation and showing as my assigned seat through printing of boarding pass. At the gate, my seat was reassigned to a middle seat. This is a huge problem for me, as my back and leg injuries require the ability to stretch and move frequently. When complaining on Delta phone lines, I was told that the seat was needed for a Diamond member and therefore was "policy" to bump. Although I eventually received some compensation for the fact I paid more for the original seat, I remain very disappointed in Delta, if this is indeed the policy."

Pros: "Very little"
Cons: "Rough weather. Stopped delivering water and snacks. Seat belt off and no attempt to continue water and snacks for 20 minutes. Then started back at front again to those who had already been served once. When got to me no snacks offered. Had to ask."

Cons: "Cramped seats entertainment"

Pros: "Punctual"
Cons: "Very poor customer service"

Pros: "We arrived where we wanted to go"
Cons: "Separated my son and I into middle seats. Made us sit on the tarmac for 30 minutes due a completely predictable issue. We should have been allowed to stay at the gate. Seating is horribly cramped. Less that friendly flight attendants. Arrived late on a red eye in perfect weather. Otherwise delightfu"

Cons: "It was all good."

Cons: "Seats are horrible with westjet"

Pros: "The wide variety options of movies/shows to watch."
Cons: "The food wasn't the best"

Pros: "Friendly crew."
Cons: "The flight was delayed"

Cons: "very poor customer service boarding and in flight."

Pros: "Friendly staff"
Cons: "guess they are a budget airline, since Millar to Rouge, Air Transat etc. Didn’t realize they weren’t a real airline company. As said, this is our first time using WestJet."

Pros: "Purchasing on Kayak was easy AND saved me $60 over the WestJet website price (purchased less than 24 hrs before flight). WestJet checkin process quick & courteous (not common in Trinidad) and the technical aspects of the flight smooth. The BEST part was a last minute $86 upgrade to Premium. I had no idea it would be comparable to First Class; complete with roomy seating, beverages, breakfast, snacks and EXCELLENT customer service. The flight crew had a sense of humor (similar to SouthWest's approach to announcements), but it was their attentiveness and respect that blew this experience sky-high."

Pros: "I slept throughout the flight"

Pros: "Crew"
Cons: "I asked for special Assistance and No records of it"

Cons: "No information"

Pros: "Plus section is very comfortable and service is very good. Food is so-so, but included in the Plus ticket price as are drinks. The flight attendants are always very accommodating and friendly and do a great job. I didn't use the entertainment system."
Cons: "Didn't care for the Turkey Crossient sandwich. All processed "Turkey" and very salty."

Pros: "Carrie (?) who looked after us in Plus was great. Was a nice flight - thx"

Pros: "The flight staff were excellent. Very pleasant to deal with and very accommodating. They really let you feel that they were there to help and if they could they did."
Cons: "The only real irritation was the check in process. I have no issue whatsoever with the 23kg allowance per bag but the process for checking your bag, especially if you were over the limit and what the consequences may be were not obvious. My wife and I had two bags, mine was 4kg under the allowance and my wife's was 2kg over. If I had known this was going to be a potential GBP45 charge we would have shuffled things about to balance the bags. It needs to be made clear to people that they can actually weigh their bags first to find this out. My bag was already tagged and gone when we went through a lot of hassle to reduce my wifes bag weight. Anyway, this is a suggestion so that future passengers do not encounter the same frustration."

Pros: "Staff was good."
Cons: "Delayed by 1 hr, no coffee or tea. Food choices very limited"

Pros: "Food vouchers in Calgary for the 6 hour flight delay due to WesJet computer issues on Toronto plane. $100 credit Bag pick up Minmico at WS Care Centre tried hard to arrange a seat on an earlier flight due to my inquiry; let me call home twice on her phone to advise husband of flight changes. She tried to organize my bag to be put on the earlier flight at the last minute although she was unsuccessful."
Cons: "Passengers are crammed into small seats."

Pros: "Fuss free check in. Crew was very friendly and helpful. Flight is on time. Will definitely travel on WestJet again."
Cons: "Nothing"

Pros: "All it was good."
Cons: "We were 25 minutes late and they did not let us board."

Pros: "The crew. Very friendly and helpful"
Cons: "The food. Pizza was bad."

Pros: "Affordable, great service, and easy"
Cons: "The internet and TV service were both broken on the flight. I missed out on much of the work I had to do. I was very disappointed that we were only told just minutes before boarding. I was not prepared to spend 5 hours on a flight with a screaming baby, unable to work or watch tv."

Pros: "Lots of leg room"
Cons: "No tv screens"

Pros: "Quiet ride, got to sit with my friends again, fast loading"
Cons: "No entertainment, tv. Seats are very uncomfortable, as well"

Pros: "That we could sleep during the flight. The attendants left us alone when we were sleeping."

Pros: "I like that there is a route from northern Vancouver Island to northern Alberta."
Cons: "There was nothing I disliked.................................."

Pros: "Nothing"
Cons: "Everything! Staff were horrible"

Pros: "Great crew services, as usual. Nice, smooth flight."
Cons: ""We're waiting for a pilot," doesn't exactly scream, "well oiled machine". How do you rate a bag of pretzels as " Food?""

Pros: "Very pleasant crew. Complimentary wine was a welcome surprise"

Pros: "No stops in US."
Cons: "Small seats."

Pros: "Carousel number although we only had carry-on"

Pros: "I liked the flight attendants sense of humour!"

Pros: "Exact on time."
Cons: "Refreshment should have more choices"

Pros: "The crew was very helpful."

Pros: "Flights were on time and luggage arrived safely."
Cons: "I couldn't access inflght movies as I didn't realize I had to have the WestJet App downloaded prior to the flight. In any event I like having a screen in front of me rather than looking at a tiny Android screen. Also on a 5 hour flight it seems we should get a hot meal rather than having to pay extra for meals."

Pros: "The seats were comfortable . Good price and no delays. I like buying just what you need (food, movies, internet) at a very decent price."

Pros: "Friendly relaxed crew. Overall organized and efficient."
Cons: "Both flights were late"

Pros: "Decent selection of movies."
Cons: "No meal included in 7hrs oversea trip. They had 3 services - two snacks and one coffee only.othereise, food was for purchase only. No checked luggage included."

Pros: "Friendly, polite crew. Well organized boarding"

Cons: "Seated @ the back & disembarking at the back door. Quick, easy on a bright sunshine day."

Cons: "No access to free WiFi."

Pros: "The crew was very nice and accommodating. Boarding was well organized and fast."
Cons: "No food and very warm on the plane."

Pros: "Not often do you feel like you really "welcomed aboard." This was not the case on our flights to and from Calgary. The staff was friendly and seemed to enjoy their jobs. That was refreshing. I did like the Westjet Connect feature. You don't have a TV screen in the back of each seat. You download the app and you get to watch TV, Movies, News all on your own device for free. A nice plus is that you can change all your devices with USB power port at each seats you never run out of a charge."
Cons: "The only thing that I did dislike was on the return we flew a 737-600 which did not leg room like the 737-800 we flew on first. The under seat storage is skimpy in the middle seat where an entertainment server is located"

Cons: "Flight was delayed over an hour and boarding took forever (much longer than usual and I fly pretty often)"

Pros: "The flight was pretty good specially during landing"

Pros: "Quickest flight ever."

Cons: "Several hours was added to my travel day when my Calgary to Seattle flight was cancelled and I was rerouted from Calgary to Vancouver to Seattle. It seems to me that if an airline initiated change that significant occurs, I should have an option given me to change my itinerary."

Pros: "same"
Cons: "same"

Pros: "The whole process from boarding to arrival was good. Nothing was acceptional or a standout. Good crew!"
Cons: "Snacks could be better!"

Pros: "Terrible! Terrible signage, terrible treatment, terrible organization!"
Cons: "Everything!"

Pros: "I like everything about it"
Cons: "Note"

Cons: "First time flying Volaris, both flights were delayed. The seats were very uncomfortable and overall bad experience."

Pros: "Nothing Horrible trip, horrible service"
Cons: "Flight was delayed by 5hrs Hard to get clear information about the delay and when we were actually going to leave. Horrible wifi in Mexico Airport. They had all passengers board the plane and then decided to refuel, so everyone sat in the airplane for 1 hour at the gate before leaving. We didn’t even get a drink of water on the plane. We were sitting in the last row in the back of the plane and when the attendant got to us it was time to land so she just skipped our row. I highly dis recommend Volaris."

Cons: "Everything needs to change! Worst airline worst service rude people. Horrific experience wish I got my money back."

Cons: "no cold air on the flight, it was so hot on the plane, it was delayed"

Cons: "I have yet to have any complaints about volaris they are economical"

Pros: "Crew was amazing and on time."
Cons: "Seats are a little hard no cushion"

Cons: "Staff, food, clean, entreatment, in one word, everything"

Pros: "Seat was comfortable, plane was quiet!"
Cons: "Terrible boarding process, with buses from the terminal to the flight ..."

Pros: "Timeliness its great to be on time."
Cons: "The seats it’s too cramped, also paying 4 dollars for a water is ridiculous and to top things off children crying the whole flight I rather spend my money on another airline"

Pros: "The crew was nice; however, the seats from LAX to MEX where extremely uncomfortable. The seats practically didn't recline at all and there was hardly any leg room. I am 5'3 and had ok legroom but it was not comfortable for taller people. Everything on the flight was being sold."
Cons: "Seats could have a bit more leg room and should recline a bit more. Water or a small beverage should be complementary."

Pros: "nothing"
Cons: "luggage waiting time and boarding"

Pros: "Nothing"
Cons: "That they could wait for me i lost the flight"

Cons: "You need more service options . Your flight was cancelled last minute. You could have informed us early."

Cons: "Asientos más blandos"

Pros: "On time due to excessive scheduled flight times"
Cons: "Boarding system , expensive and low quality food for sale on board, entertainment on board, unhelpful stewardess staff, deplaning system keep us waiting for half an hour to open the airplane door at the Cancun airport gate"

Pros: "Nothing"
Cons: "Everything"

Pros: "I liked the boarding was pretty simple and went by smoothly. The crew was very welcoming. I was happy to know that the vessel was not fully booked and therefore, had some empty seats to which I moved to. I felt fine like any other flight."
Cons: "No entertainment but that is because it was a short 3 hour flight. Nothing else to report."

Pros: "On time"
Cons: "Servicio"

Pros: "The flight was pleasant and direct. Quite and a relaxed atmosphere."
Cons: "The food aelecation was poor. No complimentary drinks or snacks. At a minimum shouldn’t this be a given?"

Pros: "Good time and no delays."

Pros: "Bad"
Cons: "No comments"

Pros: "Service was great but asking for water should not be a paying matter. They want to charge you for everything."

Cons: "The gate change of the flight was not properly notified."

Pros: "That we landed safely"
Cons: "This airline needs to be shut down please, if you’re over 5’4 it’s not for you. Seats are hard and uncomfortable, they are never on time with anything. The bilingual representatives just stare at you when you ask something in English. You’re charged $25 us if you’re 1pound over the 22 lb limit."

Cons: "The thing that I don't like is that you guys don't offer good food just snacks, and seriously that is no enough for the prise that the costumers pay for. This is just a comment, I hope you guys do something about it."

Pros: "I liked nothing, literally nothing."
Cons: "Between almost making us miss the flight because they couldn’t identify or scan the boarding passes THEY printed out (which were just little stickers on the back of our passports with no information), the flight was over 45 mins late! Additionally, the pilot said it was flight 911 to Los Angeles and then laughed and corrected himself to flight 900 - are you serious? Not a joke."

Cons: "There was no food or entertainment on this flight."

Pros: "The Valaris staff were most helpful and courteous. The flight crew was professional and the airplane appeared be just fine."
Cons: "The lack of a check-in machine and the long lines at the check-in counter were annoying. Also the legroom in the plane was minimal."

Cons: "Only snack options during my flight, was hoping to buy a meal."

Pros: "Loved that there was food offers . We were so hungry. We had been awake for 24 hours an we hadn’t eaten for hours and hours ."
Cons: "I didnt Know there was a menu option. At start of flight no one mentioned there was a menu for food choice . I saw It after our meals were handed out . My kids got a sandwich that was Jalepeno style sauce . It was too spicy for them to eat. If i had Known by the flight attendants (by them re assuring i knew Of the spice on the sandwich ) or by being told ,about the menu earlier , I wouldnt Have ordered it . That’s the only negative thing to say . Cuz their sandwich was really spicy ."

Cons: "Llegue 1 hora antes de mi vuelo y no me permitieron hacer mi check in porque “debería estar ahí 1.5 horas antes”. Me indicaron que debería comprar otro vuelo, ya que ellos no hacían cambios. Me tuve que cambiar de aerolínea y adquirir otro vuelo para el día siguiente."

Pros: "Puntuales."
Cons: "El procedimiento de abordaje es un relajo."

Cons: "Delayed and they del even the wather"

Pros: "Everything was ok."

Pros: "Cheap ticket prices."
Cons: "Flight was changed to 3 days later than we were supposed to leave. Not able to reach customer service. Kiosks in Mexico City have no idea what is happening, I had to raise my voice for someone flying to help translate. Horrible old planes with tiniest seating. Never again."

Pros: "Everything went smoothly and efficiently. I think they offered soft drinks or snacks but I was asleep."
Cons: "The fact that I was unable to use TSA Pre-Check on this airline."

Pros: "Punctuality, friendly flight crew"
Cons: "Boarding was an unorganized free-for-all"

Pros: "We boarded and left on time"
Cons: "Seats were a little small legroom wise"

Pros: "On time."

Pros: "On time"
Cons: "Bad service"

Cons: "El abordaje en La Paz, fue eterno, súper lento ."

Cons: "On time...smooth flight...thank you Volaris"

Pros: "Their great manners and service."

Pros: "I like the timelines and service crew"
Cons: "That was not fresh food no sandwich or any of that source."

Cons: "Both flights on Avianca Airlines were cancelled due to their pilots strike. MEX to BOG and BOG to UIO were both cancelled. I had to buy another ticket with short notice on another airline. Cost me a lot of money because of the short notice."

Pros: "Nothing"
Cons: "Tiny seating space. Don't be fooled by the low starting price they have a bunch of hidden fees. Cero interest in helping costimers. There are openly after people's money. I never review anything unless is alarming. Go with interjet or Jetblue or anything else. Please listen, not BIAS on this one, fam."

Pros: "Me gustaria que sean mas profecionales y respeten ustedes mismos su politica ,,para que todo salga bien en cada viaje y salgan a tiempo siempre ,o tengan otro avion disponible para cual quier emergencia"
Cons: "Siempre buscan excusas para quedar mal con el pasajero ,,si no llega tarde el avion y nos deja el otro cuando uno ase transferencia ,,salen con que el boleto esta vendido y uno sale perdiendo porque tiene uno que pagar mas o comprar otro boleto"

Pros: "I was not allowed to make changes even though not even 24 hours had passed since the booking."
Cons: "Change would cost more than flight cost."

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Chicago Midway to Costa Rica

Airlines flying from Chicago Midway to Costa Rica have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters

Mandatory masks

Masks required on board, masks provided

Social distancing seating

Middle seats unavailable to book

Pre-flight testing

Testing for antibodies, testing for symptoms

Book cheap flights from Chicago Midway Airport to Costa Rica

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2/28
Sun
3 stops
Multiple Airlines
20h 54m
SJO - MDW
5/26
Wed
2 stops
Multiple Airlines
14h 52m
MDW - SJO
6/3
Thu
3 stops
Multiple Airlines
20h 47m
SJO - MDW
5/26
Wed
2 stops
Multiple Airlines
14h 52m
MDW - SJO
6/3
Thu
2 stops
Multiple Airlines
21h 11m
SJO - MDW
2/24
Wed
2 stops
Multiple Airlines
19h 50m
MDW - SJO
2/28
Sun
3 stops
Multiple Airlines
24h 49m
SJO - MDW
3/3
Wed
2 stops
Multiple Airlines
13h 14m
MDW - SJO
3/7
Sun
2 stops
Multiple Airlines
36h 51m
SJO - MDW
3/6
Sat
2 stops
WestJet
49h 09m
MDW - LIR
3/12
Fri
2 stops
WestJet
28h 02m
LIR - MDW
3/28
Sun
2 stops
WestJet
25h 09m
MDW - LIR
4/2
Fri
2 stops
WestJet
28h 02m
LIR - MDW
Show more results

Recent one-way flight deals

1/1
Fri
1 stop
Delta
6h 40m
MDW - SJO
12/9
Wed
2 stops
Volaris
29h 10m
MDW - SJO
12/24
Thu
1 stop
Delta
6h 40m
MDW - SJO
12/28
Mon
1 stop
Delta
6h 44m
MDW - LIR
12/25
Fri
1 stop
Delta
6h 40m
MDW - SJO
12/9
Wed
3 stops
Multiple Airlines
25h 29m
MDW - SJO
12/20
Sun
1 stop
Delta
6h 44m
MDW - LIR
12/5
Sat
3 stops
Multiple Airlines
29h 45m
MDW - SJO
12/5
Sat
2 stops
Volaris
22h 46m
MDW - SJO
12/19
Sat
1 stop
Delta
6h 40m
MDW - SJO
12/4
Fri
3 stops
Multiple Airlines
31h 29m
MDW - SJO
12/4
Fri
2 stops
Multiple Airlines
47h 31m
MDW - SJO
12/26
Sat
1 stop
Delta
6h 40m
MDW - SJO
1/12
Tue
2 stops
Major Airline
19h 35m
MDW - LIR
12/26
Sat
1 stop
Delta
6h 40m
MDW - SJO
12/22
Tue
3 stops
Multiple Airlines
13h 50m
MDW - SJO
12/22
Tue
3 stops
Multiple Airlines
13h 50m
MDW - SJO
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