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Find cheap flights from Chicago Midway Airport to Costa Rica from $119

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 6/5. 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
Sat 6/29
Sat 7/6

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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$296
Liberia
Liberia1 stop$647

Good to know

Low season

August

High season

April

Cheapest flight

$119
Best time to beat the crowds but there is an average 26% increase in price.
Most popular time to fly and prices are also 0% lower on average.
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 50% 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

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 10457 reviews
8.6Crew
8.2Boarding
8.0Entertainment
7.9Comfort
7.4Food
Airline reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

Book cheap flights from Chicago to Costa Rica

Recent round-trip flight deals

6/5Wed
1 stopFrontier
19h 23mMDW-SJO
6/9Sun
1 stopFrontier
28h 11mSJO-MDW
$296
6/5Wed
1 stopFrontier
19h 23mMDW-SJO
6/13Thu
1 stopFrontier
28h 15mSJO-MDW
$325
6/13Thu
1 stop
16h 54mMDW-SJO
6/17Mon
2 stops
27h 57mSJO-MDW
$394
6/13Thu
1 stop
16h 54mMDW-SJO
6/16Sun
1 stop
20h 28mSJO-MDW
$423
7/1Mon
1 stopSouthwest
16h 45mMDW-SJO
7/4Thu
1 stopSouthwest
17h 55mSJO-MDW
$514
7/1Mon
1 stopSouthwest
16h 45mMDW-SJO
7/4Thu
2 stopsSouthwest
29h 00mSJO-MDW
$530
10/29Tue
1 stopDelta
6h 43mMDW-LIR
11/3Sun
1 stopDelta
7h 36mLIR-MDW
$647
8/9Fri
1 stopDelta
6h 43mMDW-SJO
8/20Tue
1 stopDelta
7h 38mSJO-MDW
$661
6/15Sat
2 stopsWestJet
21h 39mMDW-LIR
6/22Sat
2 stopsWestJet
21h 30mLIR-MDW
$2,965
10/29Tue
2 stopsWestJet
23h 45mMDW-LIR
11/3Sun
2 stopsWestJet
22h 31mLIR-MDW
$2,976

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Recent one-way flight deals

6/5Wed
1 stopFrontier
19h 23mMDW-SJO
$119
8/22Thu
2 stops
16h 03mMDW-SJO
$161
6/5Wed
2 stops
12h 12mMDW-SJO
$172
7/22Mon
3 stops
14h 44mMDW-SJO
$197
6/22Sat
1 stopFrontier
26h 10mMDW-SJO
$200
6/21Fri
2 stops
24h 03mMDW-SJO
$202
6/27Thu
1 stop
16h 54mMDW-SJO
$224
8/13Tue
2 stopsWestJet
21h 37mMDW-LIR
$344
8/22Thu
1 stopDelta
6h 43mMDW-SJO
$353
7/20Sat
2 stopsDelta
12h 13mMDW-SJO
$378

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Last minute flights from Midway to Costa Rica

Last minute flight, train and bus deals

6/1Sat
multi-stopFrontier
25h 23mMDW-SJO
6/9Sun
multi-stopFrontier
28h 11mSJO-MDW
$373
6/1Sat
multi-stopFrontier
25h 23mMDW-SJO
6/13Thu
multi-stopFrontier
28h 15mSJO-MDW
$403
6/3Mon
multi-stop
21h 42mMDW-SJO
6/5Wed
multi-stop
18h 49mSJO-MDW
$471
6/4Tue
multi-stopDelta
12h 28mMDW-SJO
6/14Fri
multi-stopDelta
7h 39mSJO-MDW
$1,084
6/4Tue
multi-stopDelta
11h 41mMDW-SJO
6/14Fri
multi-stopDelta
7h 39mSJO-MDW
$1,089
6/2Sun
multi-stopDelta
12h 28mMDW-SJO
6/6Thu
multi-stopDelta
14h 01mSJO-MDW
$1,300
5/31Fri
multi-stopDelta
8h 31mMDW-SJO
6/3Mon
multi-stopDelta
9h 58mSJO-MDW
$1,394
6/2Sun
multi-stopDelta
11h 41mMDW-SJO
6/6Thu
multi-stopDelta
9h 58mSJO-MDW
$1,491
5/31Fri
multi-stopDelta
11h 41mMDW-SJO
6/3Mon
multi-stopDelta
7h 47mSJO-MDW
$1,585
6/4Tue
multi-stopDelta
7h 00mMDW-LIR
6/12Wed
multi-stopDelta
7h 41mLIR-MDW
$1,651

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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: