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Cheap flights from Costa Rica to Chicago from $106

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 11/8. 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

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Find the cheapest flights from Costa Rica to Chicago

Recent round-trip flight deals from Costa Rica to Chicago

Enter your travel dates to find the best prices.
Spirit Airlines Logo
12:35 pm - 11:45 pmSJO-ORD
10h 10m1 stop
Spirit Airlines Logo
5:05 am - 11:30 amORD-SJO
7h 25m1 stop
$174Spirit Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
Spirit Airlines Logo
12:35 pm - 11:45 pmSJO-ORD
10h 10m1 stop
Spirit Airlines Logo
5:05 am - 11:30 amORD-SJO
7h 25m1 stop
$188Spirit Airlines
Find Deal
Thu, Oct 23 - Sun, Oct 26
Spirit Airlines Logo
12:35 pm - 11:45 pmSJO-ORD
10h 10m1 stop
Spirit Airlines Logo
7:43 pm - 11:30 amORD-SJO
16h 47m1 stop
$193Spirit Airlines
Find Deal
Fri, Oct 24 - Tue, Oct 28
Multiple Airlines Logo
12:35 pm - 11:45 pmSJO-ORD
10h 10m1 stop
Multiple Airlines Logo
7:43 pm - 3:13 pmORD-SJO
20h 30m2 stops
$251Multiple Airlines
Find Deal
Fri, Oct 24 - Fri, Oct 31
Multiple Airlines Logo
1:16 am - 9:23 amSJO-ORD
8h 07m1 stop
Multiple Airlines Logo
4:10 pm - 11:40 pmORD-SJO
7h 30m1 stop
$252Multiple Airlines
Find Deal
Wed, Dec 10 - Thu, Jan 29
United Airlines Logo
8:35 am - 9:16 pmLIR-ORD
12h 41m1 stop
United Airlines Logo
9:05 pm - 1:10 pmORD-LIR
16h 05m1 stop
$345United Airlines
Find Deal
Tue, Dec 16 - Thu, Jan 15
United Airlines Logo
1:20 pm - 12:15 amLIR-ORD
9h 55m1 stop
United Airlines Logo
7:10 am - 6:37 pmORD-LIR
11h 27m1 stop
$431United Airlines
Find Deal
Wed, Oct 29 - Mon, Nov 3
American Airlines Logo
1:25 pm - 11:39 pmLIR-ORD
10h 14m2 stops
American Airlines Logo
7:50 pm - 12:21 pmORD-LIR
16h 31m1 stop
$480American Airlines
Find Deal
Tue, Dec 16 - Thu, Jan 15
Alaska Airlines Logo
9:00 am - 1:09 pmLIR-ORD
28h 09m2 stops
Alaska Airlines Logo
2:06 pm - 6:01 pmORD-LIR
27h 55m2 stops
$1,516Alaska Airlines
Find Deal
Tue, Dec 16 - Thu, Jan 15
Alaska Airlines Logo
9:00 am - 2:09 pmLIR-ORD
29h 09m3 stops
Alaska Airlines Logo
2:06 pm - 6:01 pmORD-LIR
27h 55m2 stops
$1,520Alaska Airlines
Find Deal
Tue, Dec 16 - Thu, Jan 15

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
Oct 22
SJO12:35 pmSan José Juan Santamaria Intl
10h 10m
1 stop
ORD11:45 pmChicago O'Hare Intl
Oct 25
ORD5:05 amChicago O'Hare Intl
7h 25m
1 stop
SJO11:30 amSan José Juan Santamaria Intl
$174
Find similar
Spirit Airlines
Oct 23
SJO12:35 pmSan José Juan Santamaria Intl
10h 10m
1 stop
ORD11:45 pmChicago O'Hare Intl
Oct 26
ORD5:05 amChicago O'Hare Intl
7h 25m
1 stop
SJO11:30 amSan José Juan Santamaria Intl
$188
Find similar
Spirit Airlines
Oct 24
SJO12:35 pmSan José Juan Santamaria Intl
10h 10m
1 stop
ORD11:45 pmChicago O'Hare Intl
Oct 28
ORD7:43 pmChicago O'Hare Intl
16h 47m
1 stop
SJO11:30 amSan José Juan Santamaria Intl
$193
Find similar

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

Our best American Airlines deals on Costa Rica to Chicago O'Hare Intl Airport flight tickets
American Airlines
Oct 22
SJO6:44 amSan José Juan Santamaria Intl
13h 30m
1 stop
ORD9:14 pmChicago O'Hare Intl
Nov 2
ORD5:13 pmChicago O'Hare Intl
5h 00m
SJO10:13 pmSan José Juan Santamaria Intl
$405
Find similar
American Airlines
Oct 14
SJO1:00 pmSan José Juan Santamaria Intl
18h 53m
1 stop
ORD8:53 amChicago O'Hare Intl
Nov 8
ORD5:13 pmChicago O'Hare Intl
5h 00m
SJO10:13 pmSan José Juan Santamaria Intl
$411
Find similar
American Airlines
Dec 16
LIR1:25 pmLiberia
10h 14m
2 stops
ORD11:39 pmChicago O'Hare Intl
Jan 15
ORD7:50 pmChicago O'Hare Intl
16h 31m
1 stop
LIR12:21 pmLiberia
$480
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 October 9, 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 10/22

12:35 pm-11:45 pm

1 stop10h 10m

Chicago O'Hare Intl

Sat 10/25

5:05 am-11:30 am

1 stop7h 25m

$174

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 10/23

12:35 pm-11:45 pm

1 stop10h 10m

Chicago O'Hare Intl

Sun 10/26

5:05 am-11:30 am

1 stop7h 25m

$188

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 10/24

12:35 pm-11:45 pm

1 stop10h 10m

Chicago O'Hare Intl

Tue 10/28

7:43 pm-11:30 am

1 stop16h 47m

$193

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 10/24

12:35 pm-11:45 pm

1 stop10h 10m

Chicago O'Hare Intl

Fri 10/31

7:43 pm-3:13 pm

2 stops20h 30m

$251

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 12/10

1:16 am-9:23 am

1 stop8h 07m

Chicago O'Hare Intl

Thu 1/29

4:10 pm-11:40 pm

1 stop7h 30m

$252

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Tue 12/16

8:35 am-9:16 pm

1 stop12h 41m

Chicago O'Hare Intl

Thu 1/15

9:05 pm-1:10 pm

1 stop16h 05m

$345

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Wed 10/29

1:20 pm-12:15 am

1 stop9h 55m

Chicago O'Hare Intl

Mon 11/3

7:10 am-6:37 pm

1 stop11h 27m

$431

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Tue 12/16

1:25 pm-11:39 pm

2 stops10h 14m

Chicago O'Hare Intl

Thu 1/15

7:50 pm-12:21 pm

1 stop16h 31m

$480

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Tue 12/16

9:00 am-1:09 pm

2 stops28h 09m

Chicago O'Hare Intl

Thu 1/15

2:06 pm-6:01 pm

2 stops27h 55m

$1,516

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Tue 12/16

9:00 am-2:09 pm

3 stops29h 09m

Chicago O'Hare Intl

Thu 1/15

2:06 pm-6:01 pm

2 stops27h 55m

$1,520

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 November is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Costa Rica averaging around $412.

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 Thursday when prices can be found for as low as $420. 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 $601.

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 $552. 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 $465 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 $386 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?

No. A direct flight is the cheapest option for a flight between Costa Rica to Chicago O'Hare Intl Airport.

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

$243

Fastest flight time

5h 19m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Costa Rica in the past 72 hours is $243. The best round-trip flight deal from Costa Rica to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $395.
The fastest flight from Costa Rica to Chicago O'Hare Intl Airport takes 5h 19m
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
Spirit AirlinesPriceFrom $242Free CancellationRating
6.3
8,087 reviews
Search Spirit Airlines flights
AviancaPriceFrom $249Free CancellationRating
6.7
2,447 reviews
Search Avianca flights
Copa AirlinesPriceFrom $314Free CancellationRating
7.6
1,545 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $324Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
SouthwestPriceFrom $425Free CancellationRating
8.0
4,236 reviews
Search Southwest flights
United AirlinesPriceFrom $436Free CancellationRating
7.4
8,966 reviews
Search United Airlines flights

Traveling to a place near Chicago?

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