Cheap flights from Costa Rica to Chicago from $107

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 12/11. 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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
1:30 pm - 10:36 pmSJO-ORD
9h 06m1 stop
Multiple Airlines Logo
9:23 am - 3:30 pmORD-SJO
30h 07m1 stop
$263Multiple Airlines
Find Deal
Thu, Jan 22 - Tue, Jan 27
Spirit Airlines Logo
1:30 pm - 8:18 amSJO-ORD
18h 48m1 stop
Spirit Airlines Logo
5:15 am - 12:22 pmORD-SJO
7h 07m1 stop
$264Spirit Airlines
Find Deal
Fri, Jan 23 - Mon, Jan 26
Multiple Airlines Logo
1:30 pm - 10:36 pmSJO-ORD
9h 06m1 stop
Multiple Airlines Logo
2:15 pm - 12:22 pmORD-SJO
22h 07m2 stops
$265Multiple Airlines
Find Deal
Thu, Jan 29 - Fri, Feb 20
Multiple Airlines Logo
1:31 pm - 12:30 amSJO-ORD
10h 59m1 stop
Multiple Airlines Logo
2:26 pm - 1:48 pmORD-SJO
23h 22m1 stop
$267Multiple Airlines
Find Deal
Tue, Dec 23 - Tue, Jan 6
Spirit Airlines Logo
12:33 pm - 2:17 pmSJO-ORD
25h 44m2 stops
Spirit Airlines Logo
3:22 pm - 11:37 amORD-SJO
20h 15m2 stops
$269Spirit Airlines
Find Deal
Fri, Jan 30 - Mon, Feb 9
Spirit Airlines Logo
1:30 pm - 10:03 pmSJO-ORD
8h 33m1 stop
Spirit Airlines Logo
5:32 pm - 12:22 pmORD-SJO
18h 50m1 stop
$270Spirit Airlines
Find Deal
Sat, Jan 31 - Wed, Feb 18
Spirit Airlines Logo
1:30 pm - 2:17 pmSJO-ORD
24h 47m2 stops
Spirit Airlines Logo
5:15 am - 12:22 pmORD-SJO
7h 07m1 stop
$271Spirit Airlines
Find Deal
Thu, Jan 22 - Mon, Jan 26
Air Canada Logo
3:55 pm - 11:06 amLIR-ORD
19h 11m1 stop
Air Canada Logo
8:45 pm - 2:45 pmORD-LIR
18h 00m1 stop
$308Air Canada
Find Deal
Tue, Jan 20 - Sun, Jan 25
Air Canada Logo
3:55 pm - 8:10 pmLIR-ORD
28h 15m1 stop
Air Canada Logo
8:45 pm - 2:45 pmORD-LIR
18h 00m1 stop
$317Air Canada
Find Deal
Tue, Jan 20 - Sun, Jan 25
Air Canada Logo
3:45 pm - 10:05 pmLIR-ORD
30h 20m1 stop
Air Canada Logo
10:00 am - 2:45 pmORD-LIR
28h 45m1 stop
$334Air Canada
Find Deal
Tue, Jan 13 - 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
Jan 23
SJO1:30 pmSan José Juan Santamaria Intl
18h 48m
1 stop
ORD8:18 amChicago O'Hare Intl
Jan 26
ORD5:15 amChicago O'Hare Intl
7h 07m
1 stop
SJO12:22 pmSan José Juan Santamaria Intl
Spirit Airlines
Jan 30
SJO12:33 pmSan José Juan Santamaria Intl
25h 44m
2 stops
ORD2:17 pmChicago O'Hare Intl
Feb 9
ORD3:22 pmChicago O'Hare Intl
20h 15m
2 stops
SJO11:37 amSan José Juan Santamaria Intl
Spirit Airlines
Jan 31
SJO1:30 pmSan José Juan Santamaria Intl
8h 33m
1 stop
ORD10:03 pmChicago O'Hare Intl
Feb 18
ORD5:32 pmChicago O'Hare Intl
18h 50m
1 stop
SJO12:22 pmSan José Juan Santamaria Intl

Air Canada flights from Costa Rica to Chicago O'Hare Intl Airport

Our best Air Canada deals on Costa Rica to Chicago O'Hare Intl Airport flight tickets
Air Canada
Jan 20
LIR3:55 pmLiberia
19h 11m
1 stop
ORD11:06 amChicago O'Hare Intl
Jan 25
ORD8:45 pmChicago O'Hare Intl
18h 00m
1 stop
LIR2:45 pmLiberia
Air Canada
Jan 20
LIR3:55 pmLiberia
28h 15m
1 stop
ORD8:10 pmChicago O'Hare Intl
Jan 25
ORD8:45 pmChicago O'Hare Intl
18h 00m
1 stop
LIR2:45 pmLiberia
Air Canada
Jan 13
LIR3:45 pmLiberia
30h 20m
1 stop
ORD10:05 pmChicago O'Hare Intl
Jan 15
ORD10:00 amChicago O'Hare Intl
28h 45m
1 stop
LIR2:45 pmLiberia

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 November 29, 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

Thu 1/22

1:30 pm-10:36 pm

1 stop9h 06m

Chicago O'Hare Intl

Tue 1/27

9:23 am-3:30 pm

1 stop30h 07m

$263

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 1/23

1:30 pm-8:18 am

1 stop18h 48m

Chicago O'Hare Intl

Mon 1/26

5:15 am-12:22 pm

1 stop7h 07m

$264

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 1/29

1:30 pm-10:36 pm

1 stop9h 06m

Chicago O'Hare Intl

Fri 2/20

2:15 pm-12:22 pm

2 stops22h 07m

$265

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 12/23

1:31 pm-12:30 am

1 stop10h 59m

Chicago O'Hare Intl

Tue 1/6

2:26 pm-1:48 pm

1 stop23h 22m

$267

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 1/30

12:33 pm-2:17 pm

2 stops25h 44m

Chicago O'Hare Intl

Mon 2/9

3:22 pm-11:37 am

2 stops20h 15m

$269

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 1/31

1:30 pm-10:03 pm

1 stop8h 33m

Chicago O'Hare Intl

Wed 2/18

5:32 pm-12:22 pm

1 stop18h 50m

$270

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 1/22

1:30 pm-2:17 pm

2 stops24h 47m

Chicago O'Hare Intl

Mon 1/26

5:15 am-12:22 pm

1 stop7h 07m

$271

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Tue 1/20

3:55 pm-11:06 am

1 stop19h 11m

Chicago O'Hare Intl

Sun 1/25

8:45 pm-2:45 pm

1 stop18h 00m

$308

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Tue 1/20

3:55 pm-8:10 pm

1 stop28h 15m

Chicago O'Hare Intl

Sun 1/25

8:45 pm-2:45 pm

1 stop18h 00m

$317

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Tue 1/13

3:45 pm-10:05 pm

1 stop30h 20m

Chicago O'Hare Intl

Thu 1/15

10:00 am-2:45 pm

1 stop28h 45m

$334

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 February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Costa Rica averaging around $425.

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 Friday when prices can be found for as low as $448. 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 $579.

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 $525. 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 $463 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 $395 on momondo.

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

There are 2 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 1% 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

$175

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 $175. The best round-trip flight deal from Costa Rica to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $426.
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.
  • 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 $228Free CancellationRating
6.3
8,161 reviews
Search Spirit Airlines flights
AviancaPriceFrom $249Free CancellationRating
6.6
2,474 reviews
Search Avianca flights
Copa AirlinesPriceFrom $314Free CancellationRating
7.6
1,566 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $324Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
SouthwestPriceFrom $425Free CancellationRating
8.0
4,255 reviews
Search Southwest flights
United AirlinesPriceFrom $434Free CancellationRating
7.4
9,056 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
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
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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1 adult
Mon 12/29
Mon 1/5

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