Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Costa Rica from $162

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 12/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

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.
8:50 am - 11:31 amMDW-SJO
26h 41m1 stop
1:24 pm - 10:45 pmSJO-MDW
33h 21m2 stops
Mon, Dec 2 - Sat, Dec 7
5:35 am - 12:55 pmMDW-SJO
7h 20m1 stop
8:45 am - 10:20 pmSJO-MDW
12h 35m2 stops
$518Southwest
Find Deal
Sun, Mar 2 - Wed, Mar 12
8:40 am - 8:40 pmMDW-SJO
12h 00m2 stops
1:40 pm - 8:40 amSJO-MDW
19h 00m2 stops
$522Southwest
Find Deal
Fri, Dec 6 - Thu, Dec 12
5:45 am - 12:55 pmMDW-SJO
7h 10m1 stop
9:55 am - 6:50 pmSJO-MDW
8h 55m2 stops
$538Southwest
Find Deal
Wed, Feb 26 - Tue, Mar 4
6:00 am - 12:48 pmMDW-SJO
6h 48m1 stop
7:00 am - 5:01 pmSJO-MDW
10h 01m2 stops
$625Delta
Find Deal
Sat, Dec 7 - Wed, Dec 11
3:19 pm - 9:53 pmMDW-SJO
6h 34m1 stop
7:00 am - 4:12 pmSJO-MDW
9h 12m1 stop
$636Delta
Find Deal
Mon, Dec 2 - Tue, Dec 10
9:44 pm - 8:25 amMDW-SJO
10h 41m1 stop
9:40 am - 8:49 pmSJO-MDW
10h 09m1 stop
$808Frontier
Find Deal
Sat, Mar 8 - Thu, Mar 13
8:12 am - 9:25 amMDW-SJO
25h 13m1 stop
9:40 am - 8:49 pmSJO-MDW
10h 09m1 stop
$822Frontier
Find Deal
Wed, Mar 5 - Sun, Mar 16
11:19 am - 2:02 pmMDW-LIR
26h 43m2 stops
2:55 pm - 10:36 amLIR-MDW
19h 41m2 stops
$891WestJet
Find Deal
Sat, Jan 11 - Sat, Jan 18
10:19 am - 2:02 pmMDW-LIR
27h 43m3 stops
2:55 pm - 5:47 pmLIR-MDW
26h 52m2 stops
$1,173WestJet
Find Deal
Wed, Jan 15 - Sun, Jan 19
4:27 pm - 12:53 amMDW-SJO
32h 26m2 stops
Thu, Dec 5
8:12 am - 12:59 amMDW-SJO
16h 47m2 stops
Wed, Feb 26
6:10 am - 2:10 pmMDW-LIR
8h 00m1 stop
$202Southwest
Find Deal
Wed, Jan 15
8:25 am - 10:18 amMDW-SJO
25h 53m1 stop
$208Frontier
Find Deal
Wed, Jan 1
8:12 am - 12:59 amMDW-SJO
16h 47m3 stops
Wed, Feb 26
5:45 am - 12:55 pmMDW-SJO
7h 10m1 stop
$249Southwest
Find Deal
Wed, Feb 26
10:38 am - 9:57 pmMDW-SJO
11h 19m1 stop
$297Delta
Find Deal
Tue, Dec 10
6:00 am - 12:48 pmMDW-SJO
6h 48m1 stop
$299Delta
Find Deal
Tue, Dec 10
9:44 pm - 8:25 amMDW-SJO
10h 41m1 stop
$323Frontier
Find Deal
Sat, Mar 8
2:00 pm - 1:01 pmMDW-LIR
24h 01m2 stops
$1,298WestJet
Find Deal
Sat, Mar 29
12:51 pm - 11:31 amMDW-SJO
22h 40m2 stops
12:26 pm - 9:35 amSJO-MDW
21h 09m1 stop
Sun, Nov 24 - Tue, Nov 26
1:35 pm - 8:40 pmMDW-SJO
7h 05m1 stop
1:40 pm - 1:00 amSJO-MDW
11h 20m1 stop
$744Southwest
Find Deal
Sun, Nov 24 - Tue, Nov 26
8:50 am - 8:40 pmMDW-SJO
11h 50m2 stops
9:55 am - 8:35 pmSJO-MDW
10h 40m2 stops
$748Southwest
Find Deal
Sun, Nov 24 - Tue, Nov 26
5:45 am - 2:05 pmMDW-LIR
8h 20m1 stop
3:00 pm - 12:20 amLIR-MDW
9h 20m2 stops
$866Southwest
Find Deal
Mon, Nov 25 - Wed, Nov 27
10:30 pm - 2:05 pmMDW-LIR
15h 35m2 stops
3:00 pm - 12:20 amLIR-MDW
9h 20m2 stops
$870Southwest
Find Deal
Mon, Nov 25 - Wed, Nov 27
12:15 pm - 7:25 amMDW-SJO
19h 10m2 stops
12:26 pm - 7:55 amSJO-MDW
19h 29m1 stop
$1,268
Find Deal
Fri, Nov 22 - Sun, Dec 1
10:41 am - 9:53 pmMDW-SJO
11h 12m1 stop
2:12 pm - 9:46 pmSJO-MDW
7h 34m1 stop
$1,352Delta
Find Deal
Sat, Nov 23 - Sat, Nov 30
3:19 pm - 9:53 pmMDW-SJO
6h 34m1 stop
7:00 am - 5:54 pmSJO-MDW
10h 54m1 stop
$1,503Delta
Find Deal
Fri, Nov 22 - Sun, Dec 1
10:41 am - 9:53 pmMDW-SJO
11h 12m1 stop
7:00 am - 5:02 pmSJO-MDW
10h 02m2 stops
$1,508Delta
Find Deal
Sat, Nov 23 - Sat, Nov 30
6:00 am - 12:45 pmMDW-SJO
6h 45m1 stop
2:12 pm - 9:46 pmSJO-MDW
7h 34m1 stop
$1,517Delta
Find Deal
Sat, Nov 23 - Sat, Nov 30

Southwest flights from Chicago Midway Airport to Costa Rica

Our best Southwest deals on Chicago Midway Airport to Costa Rica flight tickets
Southwest
Mar 2
MDW5:35 amChicago Midway
7h 20m
1 stop
SJO12:55 pmSan José Juan Santamaria Intl
Mar 12
SJO8:45 amSan José Juan Santamaria Intl
12h 35m
2 stops
MDW10:20 pmChicago Midway
Southwest
Dec 6
MDW8:40 amChicago Midway
12h 00m
2 stops
SJO8:40 pmSan José Juan Santamaria Intl
Dec 12
SJO1:40 pmSan José Juan Santamaria Intl
19h 00m
2 stops
MDW8:40 amChicago Midway
Southwest
Feb 26
MDW5:45 amChicago Midway
7h 10m
1 stop
SJO12:55 pmSan José Juan Santamaria Intl
Mar 4
SJO9:55 amSan José Juan Santamaria Intl
8h 55m
2 stops
MDW6:50 pmChicago Midway

Delta flights from Chicago Midway Airport to Costa Rica

Our best Delta deals on Chicago Midway Airport to Costa Rica flight tickets
Delta
Dec 7
MDW6:00 amChicago Midway
6h 48m
1 stop
SJO12:48 pmSan José Juan Santamaria Intl
Dec 11
SJO7:00 amSan José Juan Santamaria Intl
10h 01m
2 stops
MDW5:01 pmChicago Midway
Delta
Dec 2
MDW3:19 pmChicago Midway
6h 34m
1 stop
SJO9:53 pmSan José Juan Santamaria Intl
Dec 10
SJO7:00 amSan José Juan Santamaria Intl
9h 12m
1 stop
MDW4:12 pmChicago Midway
Delta
Dec 2
MDW9:31 amChicago Midway
12h 22m
2 stops
SJO9:53 pmSan José Juan Santamaria Intl
Dec 10
SJO7:00 amSan José Juan Santamaria Intl
10h 01m
2 stops
MDW5:01 pmChicago 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, Saturday is the cheapest day to fly to Costa Rica from Chicago Midway Airport. The lowest ticket price found for a Saturday departure recently was $0. 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.

Can stopping save me money on Chicago Midway Airport to Costa Rica flights?

You could potentially save up to 17% on your flight if you consider stops on a Chicago Midway Airport to Costa Rica flight.

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

$162

Fastest flight time

6h 34m

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 $162. The best round-trip flight deal from Chicago Midway Airport to Costa Rica found on momondo in the last 72 hours is $514.
The fastest flight from Chicago Midway Airport to Costa Rica takes 6h 34m
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
5,005 reviews
Search Southwest flights
DeltaPriceFrom $584Free CancellationRating
8.0
8,755 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.


An easier way to manage your Costa Rica trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 11/26
Tue 12/3
Email me momondo's favorite deals

Find better results for your trip to Costa Rica