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Cheap flights from Costa Rica to Chicago from $137

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Costa Rica to Chicago departing on 8/19. 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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0 bags

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Find the cheapest flights from Costa Rica to Chicago

Recent round-trip flight deals from Costa Rica to Chicago

Spirit Airlines Logo
12:19 pm - 10:48 pmSJO-ORD
9h 29m1 stop
Spirit Airlines Logo
5:05 am - 11:14 amORD-SJO
7h 09m1 stop
$233Spirit Airlines
Find Deal
Wed, Sep 24 - Thu, Oct 2
Logo
7:30 am - 10:22 pmSJO-ORD
13h 52m1 stop
Logo
6:56 am - 3:13 pmORD-SJO
9h 17m1 stop
$234
Find Deal
Wed, Aug 20 - Sun, Aug 24
Spirit Airlines Logo
12:18 pm - 11:59 pmSJO-ORD
10h 41m1 stop
Spirit Airlines Logo
8:12 pm - 11:12 amORD-SJO
16h 00m1 stop
$235Spirit Airlines
Find Deal
Wed, Aug 27 - Sat, Aug 30
Logo
7:30 am - 10:22 pmSJO-ORD
13h 52m1 stop
Logo
6:56 am - 3:13 pmORD-SJO
9h 17m1 stop
$236
Find Deal
Wed, Aug 20 - Wed, Aug 27
United Airlines Logo
1:20 pm - 12:14 amLIR-ORD
9h 54m1 stop
United Airlines Logo
9:44 pm - 3:25 pmORD-LIR
18h 41m1 stop
$387United Airlines
Find Deal
Wed, Oct 15 - Fri, Oct 17
American Airlines Logo
2:02 pm - 9:47 amLIR-ORD
18h 45m1 stop
American Airlines Logo
7:25 pm - 11:49 amORD-LIR
17h 24m1 stop
$475American Airlines
Find Deal
Fri, Sep 5 - Sun, Sep 14
American Airlines Logo
12:49 pm - 7:42 amLIR-ORD
17h 53m2 stops
American Airlines Logo
7:25 pm - 11:49 amORD-LIR
17h 24m1 stop
$480American Airlines
Find Deal
Fri, Sep 5 - Sun, Sep 14
United Airlines Logo
1:20 pm - 10:10 amLIR-ORD
19h 50m1 stop
United Airlines Logo
7:10 am - 2:51 pmORD-LIR
32h 41m1 stop
$488United Airlines
Find Deal
Wed, Oct 1 - Fri, Oct 31
Alaska Airlines Logo
11:20 am - 5:00 amLIR-ORD
16h 40m2 stops
Alaska Airlines Logo
6:00 am - 6:20 amORD-LIR
25h 20m2 stops
$496Alaska Airlines
Find Deal
Thu, Oct 2 - Thu, Oct 30
Alaska Airlines Logo
11:20 am - 7:03 amLIR-ORD
18h 43m3 stops
Alaska Airlines Logo
7:00 am - 6:20 amORD-LIR
24h 20m2 stops
$505Alaska Airlines
Find Deal
Fri, Sep 5 - Sun, Sep 14

Spirit Airlines flights from Costa Rica to Chicago O'Hare Intl Airport

Our best Spirit Airlines deals on Costa Rica to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Sep 24
SJO12:19 pmSan José Juan Santamaria Intl
9h 29m
1 stop
ORD10:48 pmChicago O'Hare Intl
Oct 2
ORD5:05 amChicago O'Hare Intl
7h 09m
1 stop
SJO11:14 amSan José Juan Santamaria Intl
$233
Find similar
Spirit Airlines
Aug 27
SJO12:18 pmSan José Juan Santamaria Intl
10h 41m
1 stop
ORD11:59 pmChicago O'Hare Intl
Aug 30
ORD8:12 pmChicago O'Hare Intl
16h 00m
1 stop
SJO11:12 amSan José Juan Santamaria Intl
$235
Find similar
Spirit Airlines
Aug 26
SJO12:18 pmSan José Juan Santamaria Intl
10h 41m
1 stop
ORD11:59 pmChicago O'Hare Intl
Aug 30
ORD8:12 pmChicago O'Hare Intl
16h 00m
1 stop
SJO11:12 amSan José Juan Santamaria Intl
$238
Find similar

United Airlines flights from Costa Rica to Chicago O'Hare Intl Airport

Our best United Airlines deals on Costa Rica to Chicago O'Hare Intl Airport flight tickets
United Airlines
Oct 15
LIR1:20 pmLiberia
9h 54m
1 stop
ORD12:14 amChicago O'Hare Intl
Oct 17
ORD9:44 pmChicago O'Hare Intl
18h 41m
1 stop
LIR3:25 pmLiberia
$387
Find similar
United Airlines
Oct 1
LIR1:20 pmLiberia
19h 50m
1 stop
ORD10:10 amChicago O'Hare Intl
Oct 31
ORD7:10 amChicago O'Hare Intl
32h 41m
1 stop
LIR2:51 pmLiberia
$488
Find similar
United Airlines
Aug 21
LIR1:20 pmLiberia
19h 53m
1 stop
ORD10:13 amChicago O'Hare Intl
Aug 26
ORD2:20 pmChicago O'Hare Intl
22h 50m
1 stop
LIR12:10 pmLiberia
$816
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Costa Rica to Chicago O'Hare Intl Airport 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 July 31, 2025.
Use the filters below to find and compare flights from Costa Rica to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 9/24

12:19 pm-10:48 pm

1 stop9h 29m

Chicago O'Hare Intl

Thu 10/2

5:05 am-11:14 am

1 stop7h 09m

$233

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 8/20

7:30 am-10:22 pm

1 stop13h 52m

Chicago O'Hare Intl

Sun 8/24

6:56 am-3:13 pm

1 stop9h 17m

$234

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 8/27

12:18 pm-11:59 pm

1 stop10h 41m

Chicago O'Hare Intl

Sat 8/30

8:12 pm-11:12 am

1 stop16h 00m

$235

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 8/20

7:30 am-10:22 pm

1 stop13h 52m

Chicago O'Hare Intl

Wed 8/27

6:56 am-3:13 pm

1 stop9h 17m

$236

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Wed 10/15

1:20 pm-12:14 am

1 stop9h 54m

Chicago O'Hare Intl

Fri 10/17

9:44 pm-3:25 pm

1 stop18h 41m

$387

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 9/5

2:02 pm-9:47 am

1 stop18h 45m

Chicago O'Hare Intl

Sun 9/14

7:25 pm-11:49 am

1 stop17h 24m

$475

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 9/5

12:49 pm-7:42 am

2 stops17h 53m

Chicago O'Hare Intl

Sun 9/14

7:25 pm-11:49 am

1 stop17h 24m

$480

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Wed 10/1

1:20 pm-10:10 am

1 stop19h 50m

Chicago O'Hare Intl

Fri 10/31

7:10 am-2:51 pm

1 stop32h 41m

$488

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Thu 10/2

11:20 am-5:00 am

2 stops16h 40m

Chicago O'Hare Intl

Thu 10/30

6:00 am-6:20 am

2 stops25h 20m

$496

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 9/5

11:20 am-7:03 am

3 stops18h 43m

Chicago O'Hare Intl

Sun 9/14

7:00 am-6:20 am

2 stops24h 20m

$505

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 Chicago from

How to get the cheapest flight ticket from Costa Rica to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

The month of March is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Costa Rica averaging around $440.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Tuesday when prices can be found for as low as $432. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Costa Rica because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $639.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Costa Rica in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $371 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $597. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Costa Rica to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Costa Rica when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $480 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Costa Rica for as low as $401 on momondo.

What cabin class options are available on Costa Rica to Chicago O'Hare Intl flights?

There are 3 cabin classes available to choose from on Costa Rica to Chicago O'Hare Intl 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 Costa Rica to Chicago O'Hare Intl Airport flights?

You could potentially save up to 24% on your flight if you consider stops on a Costa Rica to Chicago O'Hare Intl Airport flight.

Cheap Costa Rica to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Costa Rica to Chicago O'Hare Intl Airport

Best Price Found

$137

Fastest flight time

5h 24m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Costa Rica in the past 72 hours is $137. The best round-trip flight deal from Costa Rica to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $233.
The fastest flight from Costa Rica to Chicago O'Hare Intl Airport takes 5h 24m
Direct flights go from Costa Rica to Chicago O'Hare Intl Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Costa Rica to Chicago O'Hare Intl Airport?

    Prices for flights from Costa Rica to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from Costa Rica to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Costa Rica to Chicago O'Hare Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Costa Rica to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Costa Rica to Chicago O'Hare Intl Airport?

Best airlines flying from Costa Rica to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Costa Rica to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
AviancaPriceFrom $261Free CancellationRating
6.7
2,388 reviews
Search Avianca flights
Spirit AirlinesPriceFrom $266Free CancellationRating
6.3
8,049 reviews
Search Spirit Airlines flights
Copa AirlinesPriceFrom $314Free CancellationRating
7.5
1,493 reviews
Search Copa Airlines flights
SouthwestPriceFrom $425Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
United AirlinesPriceFrom $436Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
American AirlinesPriceFrom $446Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Rockford
Schaumburg
South Haven
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Tinley Park
Elgin
Orland Park
Aurora
Janesville
Benton Harbor

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Costa Rica.

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

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

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

momondo helps you find the best flight between Costa Rica and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to Chicago from Costa Rica are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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