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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 10/2. 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
6:44 pm - 11:30 amORD-SJO
17h 46m1 stop
$177Spirit Airlines
Find Deal
Thu, Oct 2 - Sat, Oct 4
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
$179Spirit Airlines
Find Deal
Wed, Oct 1 - Sat, Oct 4
Delta Logo
1:25 pm - 12:45 pmLIR-ORD
22h 20m2 stops
Delta Logo
4:56 pm - 11:40 amORD-LIR
19h 44m2 stops
$294Delta
Find Deal
Thu, Oct 23 - Tue, Oct 28
United Airlines Logo
1:03 pm - 7:27 pmLIR-ORD
5h 24mnonstop
United Airlines Logo
9:30 pm - 3:08 pmORD-LIR
18h 38m1 stop
$309United Airlines
Find Deal
Sat, Oct 25 - Tue, Oct 28
Delta Logo
1:25 pm - 11:58 pmLIR-ORD
9h 33m1 stop
Delta Logo
5:20 am - 11:40 amORD-LIR
7h 20m1 stop
$315Delta
Find Deal
Sat, Oct 25 - Tue, Oct 28
United Airlines Logo
1:03 pm - 7:27 pmLIR-ORD
5h 24mnonstop
United Airlines Logo
6:00 am - 5:37 pmORD-LIR
12h 37m1 stop
$330United Airlines
Find Deal
Sat, Oct 25 - Thu, Oct 30
Southwest Logo
8:50 am - 6:25 pmSJO-MDW
8h 35m1 stop
Southwest Logo
5:15 am - 11:40 amMDW-SJO
7h 25m1 stop
$335Southwest
Find Deal
Tue, Sep 30 - Tue, Oct 7
Southwest Logo
9:00 am - 8:25 pmSJO-MDW
11h 25m1 stop
Southwest Logo
5:10 am - 1:15 pmMDW-SJO
8h 05m1 stop
$339Southwest
Find Deal
Sat, Nov 8 - Sat, Nov 15
American Airlines Logo
1:59 pm - 11:42 pmLIR-ORD
8h 43m1 stop
American Airlines Logo
8:26 am - 1:37 pmORD-LIR
5h 11mnonstop
$343American Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
American Airlines Logo
12:45 pm - 9:59 amLIR-ORD
20h 14m1 stop
American Airlines Logo
5:18 am - 2:07 pmORD-LIR
8h 49m1 stop
$347American Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8

American Airlines flights from Costa Rica to Chicago

Our best American Airlines deals on Costa Rica to Chicago flight tickets
American Airlines
Nov 1
LIR1:59 pmLiberia
8h 43m
1 stop
ORD11:42 pmChicago O'Hare Intl
Nov 8
ORD8:26 amChicago O'Hare Intl
5h 11m
LIR1:37 pmLiberia
$343
Find similar
American Airlines
Nov 1
LIR12:45 pmLiberia
20h 14m
1 stop
ORD9:59 amChicago O'Hare Intl
Nov 8
ORD5:18 amChicago O'Hare Intl
8h 49m
1 stop
LIR2:07 pmLiberia
$347
Find similar
American Airlines
Oct 23
LIR12:45 pmLiberia
19h 28m
2 stops
ORD9:13 amChicago O'Hare Intl
Oct 30
ORD5:00 amChicago O'Hare Intl
8h 59m
1 stop
LIR12:59 pmLiberia
$389
Find similar

Spirit Airlines flights from Costa Rica to Chicago

Our best Spirit Airlines deals on Costa Rica to Chicago flight tickets
Spirit Airlines
Oct 2
SJO12:19 pmSan José Juan Santamaria Intl
9h 29m
1 stop
ORD10:48 pmChicago O'Hare Intl
Oct 4
ORD6:44 pmChicago O'Hare Intl
17h 46m
1 stop
SJO11:30 amSan José Juan Santamaria Intl
$177
Find similar
Spirit Airlines
Oct 1
SJO12:19 pmSan José Juan Santamaria Intl
9h 29m
1 stop
ORD10:48 pmChicago O'Hare Intl
Oct 4
ORD5:05 amChicago O'Hare Intl
7h 09m
1 stop
SJO11:14 amSan José Juan Santamaria Intl
$179
Find similar
Spirit Airlines
Oct 2
SJO12:19 pmSan José Juan Santamaria Intl
9h 29m
1 stop
ORD10:48 pmChicago O'Hare Intl
Oct 4
ORD6:44 pmChicago O'Hare Intl
17h 46m
1 stop
SJO11:30 amSan José Juan Santamaria Intl
$180
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 September 17, 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

Thu 10/2

12:19 pm-10:48 pm

1 stop9h 29m

Chicago O'Hare Intl

Sat 10/4

6:44 pm-11:30 am

1 stop17h 46m

$177

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 10/1

12:19 pm-10:48 pm

1 stop9h 29m

Chicago O'Hare Intl

Sat 10/4

5:05 am-11:14 am

1 stop7h 09m

$179

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Thu 10/23

1:25 pm-12:45 pm

2 stops22h 20m

Chicago O'Hare Intl

Tue 10/28

4:56 pm-11:40 am

2 stops19h 44m

$294

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Sat 10/25

1:03 pm-7:27 pm

Nonstop5h 24m

Chicago O'Hare Intl

Tue 10/28

9:30 pm-3:08 pm

1 stop18h 38m

$309

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Sat 10/25

1:25 pm-11:58 pm

1 stop9h 33m

Chicago O'Hare Intl

Tue 10/28

5:20 am-11:40 am

1 stop7h 20m

$315

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Sat 10/25

1:03 pm-7:27 pm

Nonstop5h 24m

Chicago O'Hare Intl

Thu 10/30

6:00 am-5:37 pm

1 stop12h 37m

$330

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 9/30

8:50 am-6:25 pm

1 stop8h 35m

Chicago Midway

Tue 10/7

5:15 am-11:40 am

1 stop7h 25m

$335

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 11/8

9:00 am-8:25 pm

1 stop11h 25m

Chicago Midway

Sat 11/15

5:10 am-1:15 pm

1 stop8h 05m

$339

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Sat 11/1

1:59 pm-11:42 pm

1 stop8h 43m

Chicago O'Hare Intl

Sat 11/8

8:26 am-1:37 pm

Nonstop5h 11m

$343

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Sat 11/1

12:45 pm-9:59 am

1 stop20h 14m

Chicago O'Hare Intl

Sat 11/8

5:18 am-2:07 pm

1 stop8h 49m

$347

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 $429. If you’re not able to fly to Chicago in November, then October is your next best option. Flight prices from Costa Rica to Chicago during October average around $437.

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 $444. 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 $642.

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 $571.

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 $476 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 $386 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?

No. A direct flight is the cheapest option for a flight between Costa Rica to Chicago.

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

$194

Fastest flight time

5h 19m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun

Airports in Chicago

1 airport
The best one-way flight to Chicago from Costa Rica in the past 72 hours is $194. The best round-trip flight deal from Costa Rica to Chicago found on momondo in the last 72 hours is $395.
The fastest flight from Costa Rica to Chicago takes 5h 19m
Direct flights go from Costa Rica to Chicago on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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
AviancaPriceFrom $249Free CancellationRating
6.7
2,436 reviews
Search Avianca flights
Spirit AirlinesPriceFrom $264Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
Copa AirlinesPriceFrom $314Free CancellationRating
7.6
1,533 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $377Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $425Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $436Free CancellationRating
7.4
8,926 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
Lansing
Portage
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