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Cheap flights from Chicago Midway Airport to Costa Rica from $124

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Costa Rica departing on 5/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Costa Rica

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Costa Rica that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to Costa Rica.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Costa Rica? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Costa Rica, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Costa Rica

Find recent round-trip train or bus tickets from Chicago Midway Airport to Costa Rica.

All round-trip flight deals to Costa Rica

The cheapest plane tickets to Costa Rica found on KAYAK recently.
6:44 pm - 12:22 pmMDW-SJO
18h 38m1 stop
1:42 pm - 11:55 pmSJO-MDW
9h 13m1 stop
$315Frontier
Find Deal
Fri, May 9 - Sat, May 17
8:30 am - 11:24 amMDW-SJO
26h 54m1 stop
12:29 pm - 3:12 pmSJO-MDW
26h 43m1 stop
Tue, Feb 18 - Mon, Feb 24
4:07 pm - 11:24 amMDW-SJO
19h 17m2 stops
12:55 pm - 10:04 pmSJO-MDW
9h 09m1 stop
Tue, Feb 25 - Sat, Mar 1
8:30 am - 11:24 amMDW-SJO
26h 54m1 stop
12:55 pm - 10:04 pmSJO-MDW
9h 09m1 stop
Tue, Feb 25 - Sat, Mar 1
5:35 am - 12:55 pmMDW-SJO
7h 20m1 stop
1:55 pm - 11:40 pmSJO-MDW
8h 45m1 stop
$442Southwest
Find Deal
Tue, Mar 4 - Wed, Mar 12
7:50 am - 7:40 pmMDW-SJO
12h 50m2 stops
1:10 pm - 10:50 pmSJO-MDW
8h 40m1 stop
$520Southwest
Find Deal
Fri, May 9 - Tue, May 13
6:00 am - 12:54 pmMDW-SJO
6h 54m1 stop
7:00 am - 4:21 pmSJO-MDW
9h 21m1 stop
$638Delta
Find Deal
Fri, Jan 24 - Tue, Jan 28
12:44 pm - 10:12 pmMDW-SJO
9h 28m1 stop
7:00 am - 4:21 pmSJO-MDW
9h 21m1 stop
$668Delta
Find Deal
Thu, Jan 23 - Tue, Jan 28
10:25 am - 1:01 pmMDW-LIR
27h 36m3 stops
1:55 pm - 6:33 pmLIR-MDW
27h 38m2 stops
$939WestJet
Find Deal
Sun, Mar 23 - Fri, Mar 28
11:19 am - 2:01 pmMDW-LIR
26h 42m2 stops
8:05 am - 12:42 pmLIR-MDW
28h 37m3 stops
$1,111WestJet
Find Deal
Sat, Feb 1 - Sun, Feb 9
4:11 pm - 11:33 amMDW-SJO
20h 22m2 stops
Mon, May 19
1:04 pm - 7:35 amMDW-SJO
42h 31m2 stops
Fri, Jan 31
7:25 am - 6:55 pmMDW-SJO
12h 30m2 stops
Tue, Mar 18
6:38 pm - 11:20 amMDW-SJO
17h 42m2 stops
Mon, Mar 17
5:50 am - 12:10 pmMDW-SJO
7h 20m1 stop
$230Southwest
Find Deal
Mon, May 19
6:38 pm - 11:50 amMDW-SJO
18h 12m1 stop
$258Frontier
Find Deal
Fri, Mar 21
12:51 pm - 9:24 pmMDW-SJO
9h 33m1 stop
$300Delta
Find Deal
Tue, Mar 25
12:51 pm - 9:24 pmMDW-SJO
9h 33m1 stop
$330Delta
Find Deal
Thu, Mar 20
11:35 am - 8:40 pmMDW-SJO
9h 05m1 stop
$475Southwest
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Sat, Feb 15
10:19 am - 2:01 pmMDW-LIR
51h 42m2 stops
$1,324WestJet
Find Deal
Tue, Feb 18
10:25 am - 8:40 pmMDW-SJO
10h 15m2 stops
9:55 am - 9:25 pmSJO-MDW
11h 30m2 stops
$644Southwest
Find Deal
Mon, Jan 13 - Wed, Jan 15
5:35 am - 12:55 pmMDW-SJO
7h 20m1 stop
9:55 am - 9:45 pmSJO-MDW
11h 50m1 stop
$685Southwest
Find Deal
Mon, Jan 13 - Wed, Jan 15
8:25 am - 8:40 pmMDW-SJO
12h 15m1 stop
9:55 am - 5:35 pmSJO-MDW
7h 40m1 stop
$705Southwest
Find Deal
Tue, Jan 14 - Tue, Jan 21
7:15 am - 8:40 pmMDW-SJO
13h 25m2 stops
1:55 pm - 7:30 amSJO-MDW
17h 35m2 stops
$710Southwest
Find Deal
Tue, Jan 14 - Tue, Jan 21
6:00 am - 12:54 pmMDW-SJO
6h 54m1 stop
2:19 pm - 10:20 pmSJO-MDW
8h 01m1 stop
$713Delta
Find Deal
Sat, Jan 11 - Fri, Jan 17
10:00 am - 8:40 pmMDW-SJO
10h 40m2 stops
9:55 am - 6:50 pmSJO-MDW
8h 55m2 stops
$765Southwest
Find Deal
Sun, Jan 12 - Tue, Jan 14
8:25 am - 8:40 pmMDW-SJO
12h 15m1 stop
1:55 pm - 10:45 pmSJO-MDW
8h 50m1 stop
$790Southwest
Find Deal
Tue, Jan 14 - Mon, Jan 20
9:34 am - 10:12 pmMDW-SJO
12h 38m2 stops
2:19 pm - 10:20 pmSJO-MDW
8h 01m1 stop
$862Delta
Find Deal
Sat, Jan 11 - Sat, Jan 18
7:50 pm - 1:56 pmMDW-SJO
18h 06m3 stops
2:43 pm - 8:45 amSJO-MDW
18h 02m2 stops
$1,274
Find Deal
Tue, Jan 14 - Tue, Jan 21
10:57 am - 7:04 amMDW-LIR
20h 07m2 stops
2:55 pm - 5:43 pmLIR-MDW
26h 48m2 stops
$3,334WestJet
Find Deal
Sat, Jan 11 - Sat, Feb 8

Delta flights from Chicago Midway Airport to Costa Rica

Our best Delta deals on Chicago Midway Airport to Costa Rica flight tickets
Delta
Jan 24
MDW6:00 amChicago Midway
6h 54m
1 stop
SJO12:54 pmSan José Juan Santamaria Intl
Jan 28
SJO7:00 amSan José Juan Santamaria Intl
9h 21m
1 stop
MDW4:21 pmChicago Midway
Delta
Jan 23
MDW12:44 pmChicago Midway
9h 28m
1 stop
SJO10:12 pmSan José Juan Santamaria Intl
Jan 28
SJO7:00 amSan José Juan Santamaria Intl
9h 21m
1 stop
MDW4:21 pmChicago Midway
Delta
Jan 24
MDW6:00 amChicago Midway
6h 54m
1 stop
SJO12:54 pmSan José Juan Santamaria Intl
Jan 28
SJO7:00 amSan José Juan Santamaria Intl
11h 14m
2 stops
MDW6:14 pmChicago Midway

Southwest flights from Chicago Midway Airport to Costa Rica

Our best Southwest deals on Chicago Midway Airport to Costa Rica flight tickets
Southwest
Mar 4
MDW5:35 amChicago Midway
7h 20m
1 stop
SJO12:55 pmSan José Juan Santamaria Intl
Mar 12
SJO1:55 pmSan José Juan Santamaria Intl
8h 45m
1 stop
MDW11:40 pmChicago Midway
Southwest
May 9
MDW7:50 amChicago Midway
12h 50m
2 stops
SJO7:40 pmSan José Juan Santamaria Intl
May 13
SJO1:10 pmSan José Juan Santamaria Intl
8h 40m
1 stop
MDW10:50 pmChicago Midway
Southwest
Feb 27
MDW8:25 amChicago Midway
12h 15m
1 stop
SJO8:40 pmSan José Juan Santamaria Intl
Mar 7
SJO2:55 pmSan José Juan Santamaria Intl
10h 15m
1 stop
MDW1:10 amChicago Midway

See travel insights to Costa Rica from

How to get the cheapest flight ticket from Chicago Midway Airport to Costa Rica

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Costa Rica?

According to our data, Thursday is the cheapest day to fly to Costa Rica from Chicago Midway Airport. The lowest ticket price found for a Thursday departure recently was $633. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $1,128. These prices are subject to change though, so be sure to set up a Price Alert for flights to Costa Rica.

What is the cheapest time of day to depart on your flight to Costa Rica?

In the morning is the cheapest time of day to fly from Chicago Midway Airport to Costa Rica when you can find flight prices for as low as $779. Flying to Costa Rica in the morning is an ideal time because this is during off-peak travel hours. Flights to Costa Rica are more costly in the morning, with an average ticket price of $779. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

Cheap Chicago Midway Airport to Costa Rica flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Costa Rica

Best Price Found

$124

Fastest flight time

6h 37m

Direct flights

None

Airports in Costa Rica

2 airports
The best one-way flight to Costa Rica from Chicago Midway Airport in the past 72 hours is $124. The best round-trip flight deal from Chicago Midway Airport to Costa Rica found on momondo in the last 72 hours is $315.
The fastest flight from Chicago Midway Airport to Costa Rica takes 6h 37m
There are no direct flights from Chicago Midway Airport to Costa Rica. Popular non-direct routes for this connection are Chicago Midway Airport - Liberia Airport and Chicago Midway Airport - San José Juan Santamaria Intl Airport.
There are 2 airports near Costa Rica: Liberia (LIR), San José Juan Santamaria Intl (SJO)

  • When did momondo last update prices for flights from Chicago Midway Airport to Costa Rica?

    Prices for flights from Chicago Midway Airport to Costa Rica are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Costa Rica?

  • How old do you have to be to fly from Chicago Midway Airport to Costa Rica?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Costa Rica.

  • What documentation or ID do you need to fly to Costa Rica?

    The travel and health documents you'll need for your trip to Costa Rica may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Costa Rica. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.


Best airlines flying from Chicago Midway Airport to Costa Rica

Compare and see reviews for airlines that fly from Chicago Midway Airport to Costa Rica with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $479Free CancellationRating
8.1
4,650 reviews
Search Southwest flights
DeltaPriceFrom $584Free CancellationRating
8.0
8,501 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Costa Rica?

It is quick and easy to find Chicago to Costa Rica flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Costa Rica that suits you.

Can I find flights from Chicago to Costa Rica with flexible booking policies on momondo?

Yes. All flights to Costa Rica from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Costa Rica?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Costa Rica from Chicago.

I’m not ready to book a flight from Chicago to Costa Rica right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Costa Rica, momondo offers a useful price alert feature which will track prices for flights to Costa Rica from Chicago and alert you when they change.


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