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Cheap flights from Costa Rica to Chicago from $133

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 2/6. 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.
Spirit Airlines Logo
12:35 pm - 11:47 pm
SJO
-
ORD
11h 12m
2 stops
Spirit Airlines Logo
4:43 pm - 11:40 am
ORD
-
SJO
18h 57m
2 stops
$259Spirit Airlines
Fri, Feb 13 - Mon, Feb 16
Spirit Airlines Logo
1:30 pm - 11:47 pm
SJO
-
ORD
10h 17m
1 stop
Spirit Airlines Logo
5:15 am - 12:22 pm
ORD
-
SJO
7h 07m
1 stop
$267Spirit Airlines
Thu, Feb 5 - Sun, Feb 22
Spirit Airlines Logo
1:31 pm - 9:13 pm
SJO
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
8:59 am - 11:40 am
ORD
-
SJO
26h 41m
2 stops
$268Spirit Airlines
Sat, Feb 14 - Sat, Feb 21
Multiple Airlines Logo
1:31 pm - 11:03 pm
SJO
-
ORD
9h 32m
1 stop
Multiple Airlines Logo
4:43 pm - 11:40 am
ORD
-
SJO
18h 57m
2 stops
$283Multiple Airlines
Fri, Feb 13 - Mon, Feb 16
Air Canada Logo
2:45 pm - 1:00 pm
LIR
-
ORD
21h 15m
1 stop
Air Canada Logo
8:20 pm - 1:35 pm
ORD
-
LIR
18h 15m
1 stop
$450Air Canada
Wed, Apr 15 - Sun, Apr 19
American Airlines Logo
2:32 pm - 8:00 pm
LIR
-
ORD
5h 28mnonstop
American Airlines Logo
8:04 am - 12:18 pm
ORD
-
LIR
5h 14mnonstop
$528American Airlines
Wed, Mar 4 - Wed, Mar 11
American Airlines Logo
2:32 pm - 8:00 pm
LIR
-
ORD
5h 28mnonstop
American Airlines Logo
7:00 am - 1:13 pm
ORD
-
LIR
7h 13m
1 stop
$532American Airlines
Wed, Mar 4 - Wed, Mar 11
United Airlines Logo
2:20 pm - 7:46 am
LIR
-
ORD
17h 26m
1 stop
United Airlines Logo
7:35 am - 5:37 pm
ORD
-
LIR
11h 02m
1 stop
$533United Airlines
Wed, Mar 4 - Wed, Mar 11
United Airlines Logo
1:20 pm - 11:15 pm
LIR
-
ORD
8h 55m
1 stop
United Airlines Logo
7:52 am - 11:53 am
ORD
-
LIR
5h 01mnonstop
$538United Airlines
Wed, Apr 15 - Sun, Apr 19
Multiple Airlines Logo
2:15 pm - 11:54 am
LIR
-
ORD
21h 39m
1 stop
Multiple Airlines Logo
3:54 pm - 4:58 pm
ORD
-
LIR
26h 04m
2 stops
$600Multiple Airlines
Wed, Mar 4 - Wed, Mar 11

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
Feb 13
SJO12:35 pmSan José Juan Santamaria Intl
11h 12m
2 stops
ORD11:47 pmChicago O'Hare Intl
Feb 15
ORD7:00 amChicago O'Hare Intl
29h 22m
1 stop
SJO12:22 pmSan José Juan Santamaria Intl
$257
Spirit Airlines
Feb 13
SJO12:35 pmSan José Juan Santamaria Intl
11h 12m
2 stops
ORD11:47 pmChicago O'Hare Intl
Feb 16
ORD4:43 pmChicago O'Hare Intl
18h 57m
2 stops
SJO11:40 amSan José Juan Santamaria Intl
$259
Spirit Airlines
Feb 13
SJO1:31 pmSan José Juan Santamaria Intl
10h 16m
1 stop
ORD11:47 pmChicago O'Hare Intl
Mar 1
ORD8:59 amChicago O'Hare Intl
26h 41m
2 stops
SJO11:40 amSan José Juan Santamaria Intl
$261

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 22
LIR3:55 pmLiberia
26h 56m
1 stop
ORD6:51 pmChicago O'Hare Intl
Jan 26
ORD12:50 pmChicago O'Hare Intl
26h 05m
1 stop
LIR2:55 pmLiberia
$334
Air Canada
Apr 15
LIR2:45 pmLiberia
21h 15m
1 stop
ORD1:00 pmChicago O'Hare Intl
Apr 19
ORD8:20 pmChicago O'Hare Intl
18h 15m
1 stop
LIR1:35 pmLiberia
$450

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 January 19, 2026.
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

Fri 2/13

12:35 pm-11:47 pm

2 stops11h 12m

Chicago O'Hare Intl

Mon 2/16

4:43 pm-11:40 am

2 stops18h 57m

$259

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 2/5

1:30 pm-11:47 pm

1 stop10h 17m

Chicago O'Hare Intl

Sun 2/22

5:15 am-12:22 pm

1 stop7h 07m

$267

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 2/14

1:31 pm-9:13 pm

1 stop7h 42m

Chicago O'Hare Intl

Sat 2/21

8:59 am-11:40 am

2 stops26h 41m

$268

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 2/13

1:31 pm-11:03 pm

1 stop9h 32m

Chicago O'Hare Intl

Mon 2/16

4:43 pm-11:40 am

2 stops18h 57m

$283

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Wed 4/15

2:45 pm-1:00 pm

1 stop21h 15m

Chicago O'Hare Intl

Sun 4/19

8:20 pm-1:35 pm

1 stop18h 15m

$450

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Wed 3/4

2:32 pm-8:00 pm

Nonstop5h 28m

Chicago O'Hare Intl

Wed 3/11

8:04 am-12:18 pm

Nonstop5h 14m

$528

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Wed 3/4

2:32 pm-8:00 pm

Nonstop5h 28m

Chicago O'Hare Intl

Wed 3/11

7:00 am-1:13 pm

1 stop7h 13m

$532

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Wed 3/4

2:20 pm-7:46 am

1 stop17h 26m

Chicago O'Hare Intl

Wed 3/11

7:35 am-5:37 pm

1 stop11h 02m

$533

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Wed 4/15

1:20 pm-11:15 pm

1 stop8h 55m

Chicago O'Hare Intl

Sun 4/19

7:52 am-11:53 am

Nonstop5h 01m

$538

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Wed 3/4

2:15 pm-11:54 am

1 stop21h 39m

Chicago O'Hare Intl

Wed 3/11

3:54 pm-4:58 pm

2 stops26h 04m

$600

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 September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Costa Rica averaging around $410.

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 $416. 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 morning is the least expensive time of day to depart. momondo users have found prices as low as $460 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $466. 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 $447 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 $380 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 3% 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

$150

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 $150. The best round-trip flight deal from Costa Rica to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $296.
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 $206Free CancellationRating
6.3
8,350 reviews
Search Spirit Airlines flights
AviancaPriceFrom $249Free CancellationRating
6.6
2,496 reviews
Search Avianca flights
Copa AirlinesPriceFrom $311Free CancellationRating
7.6
1,560 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $332Free CancellationRating
7.2
11,162 reviews
Search American Airlines flights
United AirlinesPriceFrom $400Free CancellationRating
7.4
9,179 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
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
South Holland

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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