Cheap flights from Chicago to Costa Rica from $128

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 7/16. 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

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:05 am - 11:45 am
ORD
-
SJO
7h 40m
1 stop
Spirit Airlines Logo
1:00 pm - 8:22 am
SJO
-
ORD
18h 22m
1 stop
$428Spirit Airlines
Mon, May 4 - Sun, May 31
Multiple Airlines Logo
3:44 pm - 11:45 am
ORD
-
SJO
21h 01m
1 stop
Multiple Airlines Logo
1:00 pm - 11:38 pm
SJO
-
ORD
9h 38m
1 stop
$429Multiple Airlines
Sun, May 10 - Thu, May 14
Spirit Airlines Logo
8:59 pm - 11:45 am
ORD
-
SJO
15h 46m
2 stops
Spirit Airlines Logo
1:00 pm - 9:54 am
SJO
-
ORD
19h 54m
2 stops
$431Spirit Airlines
Thu, May 7 - Mon, May 11
American Airlines Logo
5:00 am - 9:36 pm
ORD
-
SJO
17h 36m
1 stop
American Airlines Logo
11:35 pm - 5:44 pm
SJO
-
ORD
17h 09m
1 stop
$432American Airlines
Sat, May 9 - Fri, May 15
Frontier Logo
6:55 am - 8:20 am
ORD
-
SJO
26h 25m
2 stops
Frontier Logo
9:35 am - 11:14 pm
SJO
-
ORD
12h 39m
1 stop
$433Frontier
Thu, Jul 16 - Mon, Jul 20
Copa Airlines Logo
3:21 pm - 7:09 am
ORD
-
SJO
16h 48m
1 stop
Copa Airlines Logo
6:19 pm - 2:06 pm
SJO
-
ORD
18h 47m
1 stop
$435Copa Airlines
Thu, Jun 18 - Tue, Jun 23
American Airlines Logo
8:19 am - 10:42 pm
ORD
-
SJO
15h 23m
1 stop
American Airlines Logo
3:19 pm - 9:10 am
SJO
-
ORD
16h 51m
1 stop
$437American Airlines
Fri, Jun 26 - Wed, Jul 15
Southwest Logo
11:10 am - 6:40 pm
MDW
-
SJO
8h 30m
2 stops
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
$472Southwest
Wed, Aug 12 - Wed, Aug 19
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
$476Southwest
Tue, Aug 18 - Tue, Aug 25
Avianca Logo
8:20 pm - 12:05 pm
ORD
-
LIR
16h 45m
1 stop
Avianca Logo
1:00 pm - 2:55 pm
LIR
-
ORD
24h 55m
1 stop
$495Avianca
Fri, Jun 12 - Sat, Jun 20

Spirit Airlines flights from Chicago to Costa Rica

Our best Spirit Airlines deals on Chicago to Costa Rica flight tickets
Spirit Airlines
May 4
ORD5:05 amChicago O'Hare Intl
7h 40m
1 stop
SJO11:45 amSan José Juan Santamaria Intl
May 31
SJO1:00 pmSan José Juan Santamaria Intl
18h 22m
1 stop
ORD8:22 amChicago O'Hare Intl
$428
Spirit Airlines
May 7
ORD8:59 pmChicago O'Hare Intl
15h 46m
2 stops
SJO11:45 amSan José Juan Santamaria Intl
May 11
SJO1:00 pmSan José Juan Santamaria Intl
19h 54m
2 stops
ORD9:54 amChicago O'Hare Intl
$431
Spirit Airlines
May 3
ORD5:05 amChicago O'Hare Intl
7h 28m
1 stop
SJO11:33 amSan José Juan Santamaria Intl
May 14
SJO1:00 pmSan José Juan Santamaria Intl
30h 11m
2 stops
ORD8:11 pmChicago O'Hare Intl
$438

American Airlines flights from Chicago to Costa Rica

Our best American Airlines deals on Chicago to Costa Rica flight tickets
American Airlines
May 9
ORD5:00 amChicago O'Hare Intl
17h 36m
1 stop
SJO9:36 pmSan José Juan Santamaria Intl
May 15
SJO11:35 pmSan José Juan Santamaria Intl
17h 09m
1 stop
ORD5:44 pmChicago O'Hare Intl
$432
American Airlines
May 5
ORD7:22 amChicago O'Hare Intl
12h 45m
2 stops
SJO7:07 pmSan José Juan Santamaria Intl
May 20
SJO6:30 amSan José Juan Santamaria Intl
12h 27m
1 stop
ORD7:57 pmChicago O'Hare Intl
$437
American Airlines
Jun 5
ORD6:00 amChicago O'Hare Intl
17h 42m
1 stop
SJO10:42 pmSan José Juan Santamaria Intl
Jun 8
SJO3:08 pmSan José Juan Santamaria Intl
17h 01m
1 stop
ORD9:09 amChicago O'Hare Intl
$441

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 April 23, 2026.
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

Cheapest round-trip

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 5/4

5:05 am-11:45 am

1 stop7h 40m

San José Juan Santamaria Intl

Sun 5/31

1:00 pm-8:22 am

1 stop18h 22m

$428

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 5/10

3:44 pm-11:45 am

1 stop21h 01m

San José Juan Santamaria Intl

Thu 5/14

1:00 pm-11:38 pm

1 stop9h 38m

$429

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 5/7

8:59 pm-11:45 am

2 stops15h 46m

San José Juan Santamaria Intl

Mon 5/11

1:00 pm-9:54 am

2 stops19h 54m

$431

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 5/9

5:00 am-9:36 pm

1 stop17h 36m

San José Juan Santamaria Intl

Fri 5/15

11:35 pm-5:44 pm

1 stop17h 09m

$432

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 7/16

6:55 am-8:20 am

2 stops26h 25m

San José Juan Santamaria Intl

Mon 7/20

9:35 am-11:14 pm

1 stop12h 39m

$433

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 6/18

3:21 pm-7:09 am

1 stop16h 48m

San José Juan Santamaria Intl

Tue 6/23

6:19 pm-2:06 pm

1 stop18h 47m

$435

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 6/26

8:19 am-10:42 pm

1 stop15h 23m

San José Juan Santamaria Intl

Wed 7/15

3:19 pm-9:10 am

1 stop16h 51m

$437

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/12

11:10 am-6:40 pm

2 stops8h 30m

San José Juan Santamaria Intl

Wed 8/19

1:40 pm-11:10 pm

1 stop8h 30m

$472
Quickest round-trip

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 8/18

6:15 am-12:45 pm

1 stop7h 30m

San José Juan Santamaria Intl

Tue 8/25

1:40 pm-11:10 pm

1 stop8h 30m

$476

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Fri 6/12

8:20 pm-12:05 pm

1 stop16h 45m

Liberia

Sat 6/20

1:00 pm-2:55 pm

1 stop24h 55m

$495

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 $308, 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 October is your next best option. Flight prices from Chicago to Costa Rica during October average around $381.

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 $513. 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 $693. 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 afternoon is the cheapest time of day to fly from Chicago to Costa Rica when you can find flight prices for as low as $514. Flying to Costa Rica in the afternoon is an ideal time because this is during off-peak travel hours. Flights to Costa Rica are more costly at noon, with an average ticket price of $664. Departure times at noon 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 Liberia for the best Chicago - Costa Rica flight prices

How far in advance should I book a flight from Chicago 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 $514 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 $438 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?

No. A direct flight is the cheapest option for a flight between Chicago to Costa Rica.

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

$366

Fastest flight time

5h 01m

Direct flights

Sun

Airports in Costa Rica

40 airports
The best one-way flight to Costa Rica from Chicago in the past 72 hours is $366. The best round-trip flight deal from Chicago to Costa Rica found on momondo in the last 72 hours is $657.
The fastest flight from Chicago to Costa Rica takes 5h 01m
Direct flights go from Chicago to Costa Rica on Sunday. There are no airlines offering direct flights.
There are 40 airports in Costa Rica. From Chicago there are direct flights to Liberia (LIR), San José Juan Santamaria Intl (SJO).

Frequently asked questions about flying from Chicago to Costa Rica

  • 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
AviancaPriceFrom $139Free CancellationRating
6.5
2,514 reviews
Search Avianca flights
DeltaPriceFrom $205Free CancellationRating
7.9
8,442 reviews
Search Delta flights
Spirit AirlinesPriceFrom $225Free CancellationRating
6.3
8,635 reviews
Search Spirit Airlines flights
Copa AirlinesPriceFrom $303Free CancellationRating
7.5
1,578 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $341Free CancellationRating
7.1
11,663 reviews
Search American Airlines flights
FrontierPriceFrom $345Free CancellationRating
5.6
2,980 reviews
Search Frontier flights
Air CanadaPriceFrom $386Free CancellationRating
7.1
10,958 reviews
Search Air Canada flights
United AirlinesPriceFrom $387Free CancellationRating
7.4
9,638 reviews
Search United Airlines flights
SouthwestPriceFrom $394Free CancellationRating
8.0
4,331 reviews
Search Southwest 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.

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.

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1 adult
Sat 5/23
Sat 5/30

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