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Cheap flights from Chicago to Costa Rica from $73

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 to Costa Rica departing on 9/7. 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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Cheap round-trip flights

Spirit Airlines Logo
9:24 pm - 12:30 pmORD-SJO
16h 06m2 stops
Spirit Airlines Logo
1:19 pm - 11:42 pmSJO-ORD
10h 23m1 stop
$285Spirit Airlines
Find Deal
sáb., nov. 1 - mié., nov. 5
Spirit Airlines Logo
9:24 pm - 12:30 pmORD-SJO
16h 06m2 stops
Spirit Airlines Logo
1:35 pm - 7:16 pmSJO-ORD
29h 41m2 stops
$287Spirit Airlines
Find Deal
sáb., nov. 1 - mar., nov. 4
Delta Logo
6:00 am - 12:50 pmMDW-SJO
6h 50m1 stop
Delta Logo
2:17 pm - 9:44 pmSJO-MDW
7h 27m1 stop
$394Delta
Find Deal
jue., nov. 6 - mié., nov. 12
Delta Logo
9:30 am - 10:15 pmMDW-SJO
12h 45m2 stops
Delta Logo
7:00 am - 9:44 pmSJO-MDW
14h 44m1 stop
$398Delta
Find Deal
mié., nov. 19 - mar., nov. 25
Southwest Logo
6:15 am - 12:45 pmMDW-SJO
7h 30m1 stop
Southwest Logo
1:40 pm - 11:20 pmSJO-MDW
8h 40m1 stop
$427Southwest
Find Deal
mar., sep. 23 - mar., sep. 30
Southwest Logo
8:05 pm - 12:05 pmMDW-SJO
17h 00m2 stops
Southwest Logo
1:30 pm - 12:05 amSJO-MDW
9h 35m2 stops
$431Southwest
Find Deal
lun., oct. 20 - vie., oct. 24
American Airlines Logo
6:00 am - 1:01 pmORD-LIR
8h 01m1 stop
American Airlines Logo
12:49 pm - 11:48 pmLIR-ORD
9h 59m2 stops
$477American Airlines
Find Deal
dom., sep. 7 - mar., sep. 9
American Airlines Logo
5:20 am - 11:25 amORD-LIR
7h 05m1 stop
American Airlines Logo
12:45 pm - 10:31 pmLIR-ORD
8h 46m1 stop
$493American Airlines
Find Deal
sáb., oct. 11 - mié., oct. 15
United Airlines Logo
6:00 am - 12:10 pmORD-LIR
7h 10m1 stop
United Airlines Logo
1:03 pm - 7:27 pmLIR-ORD
5h 24mnonstop
$503United Airlines
Find Deal
sáb., oct. 4 - sáb., oct. 11
United Airlines Logo
6:00 am - 12:10 pmORD-LIR
7h 10m1 stop
United Airlines Logo
1:03 pm - 7:27 pmLIR-ORD
5h 24mnonstop
$575United Airlines
Find Deal
sáb., oct. 11 - sáb., oct. 18

Spirit Airlines flights from Chicago to Costa Rica

Our best Spirit Airlines deals on Chicago to Costa Rica flight tickets
Spirit Airlines
Nov 1
ORD9:24 pmChicago O'Hare Intl
16h 06m
2 stops
SJO12:30 pmSan José Juan Santamaria Intl
Nov 5
SJO1:19 pmSan José Juan Santamaria Intl
10h 23m
1 stop
ORD11:42 pmChicago O'Hare Intl
$285
Find similar
Spirit Airlines
Nov 1
ORD9:24 pmChicago O'Hare Intl
16h 06m
2 stops
SJO12:30 pmSan José Juan Santamaria Intl
Nov 4
SJO1:35 pmSan José Juan Santamaria Intl
29h 41m
2 stops
ORD7:16 pmChicago O'Hare Intl
$287
Find similar
Spirit Airlines
Sep 2
ORD5:05 amChicago O'Hare Intl
7h 07m
1 stop
SJO11:12 amSan José Juan Santamaria Intl
Sep 8
SJO12:19 pmSan José Juan Santamaria Intl
9h 29m
1 stop
ORD10:48 pmChicago O'Hare Intl
$288
Find similar

Frontier flights from Chicago to Costa Rica

Our best Frontier deals on Chicago to Costa Rica flight tickets
Frontier
Oct 18
MDW6:15 amChicago Midway
7h 19m
1 stop
SJO12:34 pmSan José Juan Santamaria Intl
Oct 25
SJO1:49 pmSan José Juan Santamaria Intl
8h 36m
1 stop
MDW11:25 pmChicago Midway
$364
Find similar
Frontier
Aug 23
MDW6:10 amChicago Midway
7h 14m
1 stop
SJO12:24 pmSan José Juan Santamaria Intl
Aug 30
SJO1:53 pmSan José Juan Santamaria Intl
19h 15m
1 stop
MDW10:08 amChicago Midway
$408
Find similar
Frontier
Oct 17
MDW6:24 pmChicago Midway
19h 10m
2 stops
SJO12:34 pmSan José Juan Santamaria Intl
Oct 25
SJO1:49 pmSan José Juan Santamaria Intl
8h 36m
1 stop
MDW11:25 pmChicago Midway
$443
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Costa Rica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated agosto 20, 2025.
Use the filters below to find and compare flights from Chicago to Costa Rica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

sáb. 11/1

9:24 pm-12:30 pm

2 stops16h 06m

San José Juan Santamaria Intl

mié. 11/5

1:19 pm-11:42 pm

1 stop10h 23m

$285

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

sáb. 11/1

9:24 pm-12:30 pm

2 stops16h 06m

San José Juan Santamaria Intl

mar. 11/4

1:35 pm-7:16 pm

2 stops29h 41m

$287

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

jue. 11/6

6:00 am-12:50 pm

1 stop6h 50m

San José Juan Santamaria Intl

mié. 11/12

2:17 pm-9:44 pm

1 stop7h 27m

$394

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mié. 11/19

9:30 am-10:15 pm

2 stops12h 45m

San José Juan Santamaria Intl

mar. 11/25

7:00 am-9:44 pm

1 stop14h 44m

$398

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mar. 9/23

6:15 am-12:45 pm

1 stop7h 30m

San José Juan Santamaria Intl

mar. 9/30

1:40 pm-11:20 pm

1 stop8h 40m

$427

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

lun. 10/20

8:05 pm-12:05 pm

2 stops17h 00m

San José Juan Santamaria Intl

vie. 10/24

1:30 pm-12:05 am

2 stops9h 35m

$431

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

dom. 9/7

6:00 am-1:01 pm

1 stop8h 01m

Liberia

mar. 9/9

12:49 pm-11:48 pm

2 stops9h 59m

$477

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

sáb. 10/11

5:20 am-11:25 am

1 stop7h 05m

Liberia

mié. 10/15

12:45 pm-10:31 pm

1 stop8h 46m

$493

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

sáb. 10/4

6:00 am-12:10 pm

1 stop7h 10m

Liberia

sáb. 10/11

1:03 pm-7:27 pm

Nonstop5h 24m

$503

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

sáb. 10/11

6:00 am-12:10 pm

1 stop7h 10m

Liberia

sáb. 10/18

1:03 pm-7:27 pm

Nonstop5h 24m

$575

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Costa Rica from

How to get the cheapest flight ticket from Chicago 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 month to fly to Costa Rica?

The cheapest month to fly to Costa Rica from Chicago is in September. Flight prices, which tend to average around $445, are often lower during this time because this is during the off-season. If you’re not able to fly to Costa Rica in September, then July is your next best option. Flight prices from Chicago to Costa Rica during July average around $455.

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

According to our data, Tuesday is the cheapest day to fly to Costa Rica from Chicago. The lowest ticket price found for a Tuesday departure recently was $541. 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 Saturday because tickets tend to average around $822. 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 evening is the cheapest time of day to fly from Chicago to Costa Rica when you can find flight prices for as low as $436. Flying to Costa Rica in the evening 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 $768. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Costa Rica flight route?

Fly from Chicago O'Hare Intl to San José Juan Santamaria Intl for the best Chicago - Costa Rica flight prices

How far in advance should I book a flight to Costa Rica?

You are more likely to see cheaper flights to Costa Rica from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Costa Rica for around $601 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Costa Rica from Chicago for as low as $457 on momondo.

What cabin class options are available on Chicago to Costa Rica flights?

There are 3 cabin classes available to choose from on Chicago to Costa Rica flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

You could potentially save up to 40% on your flight if you consider stops on a Chicago to Costa Rica flight.

Cheap Chicago to Costa Rica flight deals and tips

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

Best Price Found

$268

Fastest flight time

5h 02m

Direct flights

Every day

Airports in Costa Rica

2 airports
The best one-way flight to Costa Rica from Chicago in the past 72 hours is $268. The best round-trip flight deal from Chicago to Costa Rica found on momondo in the last 72 hours is $563.
The fastest flight from Chicago to Costa Rica takes 5h 02m
Direct flights go from Chicago to Costa Rica every day.
There are 2 airports near Costa Rica: Liberia (LIR), San José Juan Santamaria Intl (SJO)
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  • When did momondo last update prices for flights from Chicago to Costa Rica?

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Costa Rica.

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

    The necessary travel and health documents for your Costa Rica trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Costa Rica?

Best airlines flying from Chicago to Costa Rica

Compare and see reviews for airlines that fly from Chicago to Costa Rica with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $275Free CancellationRating
6.3
8,039 reviews
Search Spirit Airlines flights
AviancaPriceFrom $319Free CancellationRating
6.7
2,411 reviews
Search Avianca flights
Copa AirlinesPriceFrom $343Free CancellationRating
7.5
1,510 reviews
Search Copa Airlines flights
SouthwestPriceFrom $431Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
JetBluePriceFrom $432Free CancellationRating
7.2
2,916 reviews
Search JetBlue flights
DeltaPriceFrom $438Free CancellationRating
7.9
7,982 reviews
Search Delta flights
American AirlinesPriceFrom $444Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $470Free CancellationRating
7.4
8,928 reviews
Search United Airlines flights

Why use momondo?

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

Finding the right flight to Costa Rica from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Costa Rica quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Chicago to Costa Rica flights to just show those with flexible booking policies.

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

Once all potential Chicago to Costa Rica flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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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