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Find cheap flights from Chicago Midway Airport to Costa Rica from $77

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Costa Rica departing on 5/15. 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
0 bags
Thu 6/6
Thu 6/13

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Best Costa Rica Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

San José
San José1 stop$258
Liberia
Liberia1 stop$701

Good to know

Low season

July

High season

April

Cheapest flight

$77
Best time to beat the crowds but there is an average 26% increase in price.
Most popular time to fly with an average 4% increase in price.
Flight from Chicago Midway Airport to San José

FAQs - booking Costa Rica flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Costa Rica?

    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 Midway Airport to Costa Rica.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Costa Rica?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Costa Rica from Chicago Midway 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 Midway Airport to Costa Rica?

    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 Costa Rica with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Costa Rica?

    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 Costa Rica from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Costa Rica

  • Morning departure is around 11% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top airline flying from Midway to Costa Rica

 
Need help choosing which airline to fly with from Midway to Costa Rica? 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.
8.0
DeltaOverall score based on 10810 reviews
7.4Food
8.0Entertainment
8.6Crew
8.2Boarding
7.9Comfort
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

Book cheap flights from Chicago to Costa Rica

Recent round-trip flight deals

5/21Tue
1 stop
26h 11mMDW-SJO
5/28Tue
1 stop
16h 12mSJO-MDW
$258
5/30Thu
2 stops
12h 45mMDW-SJO
6/3Mon
1 stop
29h 01mSJO-MDW
$299
6/5Wed
1 stopFrontier
19h 23mMDW-SJO
6/9Sun
1 stopFrontier
28h 11mSJO-MDW
$336
8/14Wed
1 stopFrontier
25h 58mMDW-SJO
8/18Sun
1 stopFrontier
24h 15mSJO-MDW
$342
10/22Tue
1 stopDelta
6h 53mMDW-SJO
10/29Tue
1 stopDelta
7h 31mSJO-MDW
$590
10/20Sun
1 stopDelta
6h 53mMDW-SJO
10/27Sun
1 stopDelta
7h 31mSJO-MDW
$603
6/1Sat
3 stopsWestJet
20h 32mMDW-LIR
6/5Wed
2 stopsWestJet
27h 42mLIR-MDW
$904
6/1Sat
3 stopsWestJet
20h 32mMDW-LIR
6/9Sun
2 stopsWestJet
28h 11mLIR-MDW
$1,077
6/6Thu
2 stopsLATAM Airlines
34h 40mMDW-SJO
6/11Tue
2 stopsLATAM Airlines
41h 50mSJO-MDW
$1,801
6/18Tue
2 stopsLATAM Airlines
34h 40mMDW-SJO
6/25Tue
2 stopsLATAM Airlines
41h 50mSJO-MDW
$1,976

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Recent one-way flight deals

5/15Wed
1 stopFrontier
26h 16mMDW-SJO
$77
5/21Tue
1 stop
26h 11mMDW-SJO
$112
5/21Tue
2 stops
22h 28mMDW-SJO
$113
5/14Tue
1 stop
16h 30mMDW-SJO
$118
5/13Mon
2 stops
39h 38mMDW-SJO
$124
6/5Wed
1 stopFrontier
19h 23mMDW-SJO
$168
8/12Mon
1 stopDelta
6h 53mMDW-SJO
$299
7/9Tue
1 stopDelta
10h 57mMDW-SJO
$373
5/14Tue
2 stopsWestJet
28h 47mMDW-LIR
$501
5/28Tue
2 stopsWestJet
23h 17mMDW-LIR
$1,255

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Last minute flights from Midway to Costa Rica

Last minute flight, train and bus deals

5/11Sat
multi-stop
16h 55mMDW-SJO
5/21Tue
multi-stop
16h 12mSJO-MDW
$308
5/11Sat
multi-stopFrontier
26h 21mMDW-SJO
5/16Thu
multi-stopFrontier
9h 37mSJO-MDW
$309
5/11Sat
multi-stop
16h 55mMDW-SJO
5/21Tue
multi-stop
10h 20mSJO-MDW
$346
5/11Sat
multi-stop
16h 55mMDW-SJO
5/14Tue
multi-stop
12h 40mSJO-MDW
$351
5/12Sun
multi-stop
15h 50mMDW-SJO
5/21Tue
multi-stop
16h 12mSJO-MDW
$352
5/11Sat
multi-stopFrontier
26h 21mMDW-SJO
5/23Thu
multi-stopFrontier
9h 37mSJO-MDW
$392
5/12Sun
multi-stopDelta
6h 44mMDW-SJO
5/24Fri
multi-stopDelta
9h 58mSJO-MDW
$1,074
5/12Sun
multi-stopDelta
11h 41mMDW-SJO
5/24Fri
multi-stopDelta
7h 50mSJO-MDW
$1,079
5/9Thu
multi-stopWestJet
24h 50mMDW-LIR
5/11Sat
multi-stopWestJet
27h 42mLIR-MDW
$3,295
5/10Fri
multi-stopWestJet
21h 47mMDW-LIR
5/15Wed
multi-stopWestJet
21h 27mLIR-MDW
$3,296

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Chicago Midway Airport - Costa Rica Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Costa Rica - Chicago Midway Airport

Cabin classes: