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Cheap flights from Costa Rica to Chicago from $122

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 12/16. 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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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
1:31 pm - 12:09 amSJO-ORD
10h 38m1 stop
Spirit Airlines Logo
5:00 am - 12:25 pmORD-SJO
7h 25m1 stop
$220Spirit Airlines
Find Deal
Sat, Dec 6 - Tue, Dec 9
Spirit Airlines Logo
1:30 pm - 12:27 amSJO-ORD
10h 57m1 stop
Spirit Airlines Logo
5:10 am - 12:25 pmORD-SJO
7h 15m1 stop
$224Spirit Airlines
Find Deal
Sat, Nov 15 - Tue, Nov 18
Spirit Airlines Logo
1:16 am - 9:23 amSJO-ORD
8h 07m1 stop
Spirit Airlines Logo
5:05 am - 12:14 pmORD-SJO
7h 09m1 stop
$226Spirit Airlines
Find Deal
Tue, Jan 13 - Wed, Jan 28
Avianca Logo
5:00 am - 2:50 pmSJO-ORD
9h 50m1 stop
Avianca Logo
4:10 pm - 11:40 pmORD-SJO
7h 30m1 stop
$264Avianca
Find Deal
Tue, Jan 20 - Tue, Jan 27
Avianca Logo
4:15 pm - 1:15 pmSJO-ORD
21h 00m1 stop
Avianca Logo
4:10 pm - 8:40 amORD-SJO
16h 30m1 stop
$275Avianca
Find Deal
Tue, Jan 20 - Sat, Jan 24
Southwest Logo
1:45 pm - 10:25 pmSJO-MDW
8h 40m1 stop
Southwest Logo
10:30 am - 7:30 pmMDW-SJO
9h 00m1 stop
$342Southwest
Find Deal
Fri, Feb 6 - Mon, Feb 9
Southwest Logo
9:00 am - 8:25 pmSJO-MDW
11h 25m1 stop
Southwest Logo
5:05 am - 1:15 pmMDW-SJO
8h 10m1 stop
$366Southwest
Find Deal
Sat, Nov 8 - Tue, Nov 11
United Airlines Logo
12:50 pm - 6:55 pmLIR-ORD
30h 05m1 stop
United Airlines Logo
9:25 am - 2:40 pmORD-LIR
5h 15mnonstop
$561United Airlines
Find Deal
Thu, Dec 11 - Thu, Dec 18
United Airlines Logo
1:01 pm - 7:20 pmLIR-ORD
5h 19mnonstop
United Airlines Logo
6:15 pm - 2:52 pmORD-LIR
21h 37m1 stop
$569United Airlines
Find Deal
Wed, Mar 25 - Fri, Apr 17
American Airlines Logo
1:25 pm - 11:46 pmLIR-ORD
10h 21m2 stops
American Airlines Logo
8:35 pm - 10:44 amORD-LIR
14h 09m1 stop
$744American Airlines
Find Deal
Thu, Dec 11 - Thu, Dec 18

Avianca flights from Costa Rica to Chicago

Our best Avianca deals on Costa Rica to Chicago flight tickets
Avianca
Jan 20
SJO5:00 amSan José Juan Santamaria Intl
9h 50m
1 stop
ORD2:50 pmChicago O'Hare Intl
Jan 27
ORD4:10 pmChicago O'Hare Intl
7h 30m
1 stop
SJO11:40 pmSan José Juan Santamaria Intl
$264
Find similar
Avianca
Jan 20
SJO4:15 pmSan José Juan Santamaria Intl
21h 00m
1 stop
ORD1:15 pmChicago O'Hare Intl
Jan 24
ORD4:10 pmChicago O'Hare Intl
16h 30m
1 stop
SJO8:40 amSan José Juan Santamaria Intl
$275
Find similar
Avianca
Dec 9
SJO5:00 amSan José Juan Santamaria Intl
9h 50m
1 stop
ORD2:50 pmChicago O'Hare Intl
Jan 8
ORD4:10 pmChicago O'Hare Intl
19h 15m
1 stop
SJO11:25 amSan José Juan Santamaria Intl
$281
Find similar

Spirit Airlines flights from Costa Rica to Chicago

Our best Spirit Airlines deals on Costa Rica to Chicago flight tickets
Spirit Airlines
Nov 7
SJO1:30 pmSan José Juan Santamaria Intl
10h 57m
1 stop
ORD12:27 amChicago O'Hare Intl
Nov 16
ORD5:10 amChicago O'Hare Intl
7h 15m
1 stop
SJO12:25 pmSan José Juan Santamaria Intl
$218
Find similar
Spirit Airlines
Dec 6
SJO1:31 pmSan José Juan Santamaria Intl
10h 38m
1 stop
ORD12:09 amChicago O'Hare Intl
Dec 9
ORD5:00 amChicago O'Hare Intl
7h 25m
1 stop
SJO12:25 pmSan José Juan Santamaria Intl
$220
Find similar
Spirit Airlines
Nov 15
SJO1:30 pmSan José Juan Santamaria Intl
10h 57m
1 stop
ORD12:27 amChicago O'Hare Intl
Nov 18
ORD5:10 amChicago O'Hare Intl
7h 15m
1 stop
SJO12:25 pmSan José Juan Santamaria Intl
$224
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Costa Rica to Chicago 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 29, 2025.
Use the filters below to find and compare flights from Costa Rica to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 12/6

1:31 pm-12:09 am

1 stop10h 38m

Chicago O'Hare Intl

Tue 12/9

5:00 am-12:25 pm

1 stop7h 25m

$220

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 11/15

1:30 pm-12:27 am

1 stop10h 57m

Chicago O'Hare Intl

Tue 11/18

5:10 am-12:25 pm

1 stop7h 15m

$224

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 1/13

1:16 am-9:23 am

1 stop8h 07m

Chicago O'Hare Intl

Wed 1/28

5:05 am-12:14 pm

1 stop7h 09m

$226

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 1/20

5:00 am-2:50 pm

1 stop9h 50m

Chicago O'Hare Intl

Tue 1/27

4:10 pm-11:40 pm

1 stop7h 30m

$264

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 1/20

4:15 pm-1:15 pm

1 stop21h 00m

Chicago O'Hare Intl

Sat 1/24

4:10 pm-8:40 am

1 stop16h 30m

$275

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 2/6

1:45 pm-10:25 pm

1 stop8h 40m

Chicago Midway

Mon 2/9

10:30 am-7:30 pm

1 stop9h 00m

$342

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 11/8

9:00 am-8:25 pm

1 stop11h 25m

Chicago Midway

Tue 11/11

5:05 am-1:15 pm

1 stop8h 10m

$366

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Thu 12/11

12:50 pm-6:55 pm

1 stop30h 05m

Chicago O'Hare Intl

Thu 12/18

9:25 am-2:40 pm

Nonstop5h 15m

$561

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Wed 3/25

1:01 pm-7:20 pm

Nonstop5h 19m

Chicago O'Hare Intl

Fri 4/17

6:15 pm-2:52 pm

1 stop21h 37m

$569

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Thu 12/11

1:25 pm-11:46 pm

2 stops10h 21m

Chicago O'Hare Intl

Thu 12/18

8:35 pm-10:44 am

1 stop14h 09m

$744

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

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?

The month of November is, on average, the cheapest month to fly to Chicago from Costa Rica, with most prices found around $410. If you’re not able to fly to Chicago in November, then January is your next best option. Flight prices from Costa Rica to Chicago during January average around $428.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago 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. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Costa Rica to Chicago for around $597.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Costa Rica to Chicago during this time can be as low as $335. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $541.

What is the cheapest Costa Rica to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Costa Rica when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago 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 from Costa Rica for as low as $387 on momondo.

What cabin class options are available on Costa Rica to Chicago flights?

There are 3 cabin classes available to choose from on Costa Rica to Chicago 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 flights?

You could potentially save up to 25% on your flight if you consider stops on a Costa Rica to Chicago flight.

Cheap Costa Rica to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Costa Rica to Chicago

Best Price Found

$163

Fastest flight time

5h 19m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Costa Rica in the past 72 hours is $163. The best round-trip flight deal from Costa Rica to Chicago found on momondo in the last 72 hours is $325.
The fastest flight from Costa Rica to Chicago takes 5h 19m
Direct flights go from Costa Rica to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • When did momondo last update prices for flights from Costa Rica to Chicago?

    Prices for flights from Costa Rica to Chicago refresh daily.

  • How many operators does momondo search for flights from Costa Rica to Chicago?

  • How old do you have to be to fly from Costa Rica to Chicago?

    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 Costa Rica to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Costa Rica to Chicago?

Best airlines flying from Costa Rica to Chicago

Compare and see reviews for airlines that fly from Costa Rica to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $237Free CancellationRating
6.3
8,113 reviews
Search Spirit Airlines flights
AviancaPriceFrom $249Free CancellationRating
6.6
2,468 reviews
Search Avianca flights
Copa AirlinesPriceFrom $314Free CancellationRating
7.6
1,561 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $324Free CancellationRating
7.2
11,032 reviews
Search American Airlines flights
SouthwestPriceFrom $425Free CancellationRating
8.0
4,241 reviews
Search Southwest flights
United AirlinesPriceFrom $434Free CancellationRating
7.4
9,001 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

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. All flights to Chicago from Costa Rica on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Costa Rica to Chicago.

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

Yes momondo offers price alerts on flights to Chicago from Costa Rica. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport