$202 Find Cheap Flights from Costa Rica to Chicago - Compare and Save

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Cheap Flights from Costa Rica to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Costa Rica to Chicago

Wed, Nov 18 - Tue, Dec 1
Air Canada Logo
3:10 pm - 1:13 pmLIR  Liberia-ORD Chicago O'Hare Intl
22h 03m1 stop Toronto Pearson Intl
Air Canada Logo
10:05 am - 2:10 pmORD  Chicago O'Hare Intl-LIR Liberia
28h 05m1 stop Toronto Pearson Intl
$323Air Canada
Wed, Nov 18 - Tue, Dec 1
Air Canada Logo
3:10 pm - 1:13 pmLIR  Liberia-ORD Chicago O'Hare Intl
22h 03m1 stop Toronto Pearson Intl
Air Canada Logo
1:55 pm - 2:20 pmORD  Chicago O'Hare Intl-LIR Liberia
24h 25m2 stops Toronto Island Montreal Pierre Elliott Trudeau Intl
$367Air Canada
Fri, Jan 22 - Wed, Jan 27
United Airlines Logo
1:25 pm - 6:57 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
5h 32mnonstop
United Airlines Logo
7:02 am - 12:15 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
5h 13mnonstop
$403United Airlines
Fri, Jan 29 - Tue, Feb 2
United Airlines Logo
1:25 pm - 6:57 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
5h 32mnonstop
United Airlines Logo
5:30 am - 8:39 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
15h 09m1 stop Houston George Bush Intcntl
$403United Airlines
Mon, Apr 19 - Mon, Apr 26
Avianca Logo
9:25 am - 9:20 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
10h 55m1 stop Bogotá El Dorado
Avianca Logo
11:20 pm - 3:25 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
17h 05m1 stop Bogotá El Dorado
$403Avianca
Sun, Jan 24 - Sun, Jan 31
Avianca Logo
1:50 am - 8:30 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
18h 40m1 stop Bogotá El Dorado
Avianca Logo
10:30 pm - 8:50 amORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
10h 20m1 stop Bogotá El Dorado
$403Avianca
Tue, Jan 26 - Sat, Feb 13
Copa Airlines Logo
2:15 pm - 12:46 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
22h 31m1 stop Panama City Tocumen Intl
Copa Airlines Logo
2:13 pm - 7:04 amORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
16h 51m1 stop Panama City Tocumen Intl
$406Copa Airlines
Tue, Jan 19 - Mon, Jan 25
Copa Airlines Logo
6:02 pm - 12:46 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
18h 44m1 stop Panama City Tocumen Intl
Copa Airlines Logo
2:13 pm - 7:02 amORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
16h 49m1 stop Panama City Tocumen Intl
$406Copa Airlines
Fri, Dec 25 - Sat, Jan 2
American Airlines Logo
3:08 pm - 7:35 amSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
16h 27m1 stop Dallas/Fort Worth
American Airlines Logo
5:21 am - 12:31 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
7h 10m1 stop Charlotte Douglas
$418American Airlines
Fri, Dec 25 - Sat, Jan 2
American Airlines Logo
3:08 pm - 7:35 amSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
16h 27m1 stop Dallas/Fort Worth
American Airlines Logo
5:21 am - 12:31 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
7h 10m1 stop Charlotte Douglas
$418American Airlines
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest day to fly to Chicago?

Based on KAYAK data, the cheapest day to fly to Chicago is Friday where round-trip tickets can be as cheap as $417. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $612 on average.

What is the cheapest month to fly to Chicago?

The cheapest month for flights to Chicago is January, where tickets cost $396 on average for return flights. On the other hand, the most expensive months are July and March, where the average cost of tickets from Costa Rica is $639 and $569 respectively. For one-way flights, the best month to travel is December with an average price of $289.

What is the cheapest time of day to fly to Chicago?

The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost $470 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is $486.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Liberia $317 round-trip.

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

To get a below average price, you should book around 4 weeks before departure, which saves you about 7% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $126.

Good to know

Low season

March

Cheapest flight

$202
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Liberia to Chicago

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    9 miles away from Chicago’s city center, Chicago Midway Airport is the closest of the 3 major airports in the city. There are 16 miles separating Chicago city center to Chicago O'Hare Airport, and 79 miles to Chicago Greater Rockford.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $395. The cheapest price found on KAYAK in the last 2 weeks cost $166 and departed from Liberia Airport.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many direct flights to Chicago are there each week?

    Each week there are around 44,453 direct flights from within Costa Rica to Chicago. The most common day for departures is Sunday, with 17% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $235 or less one-way and $363 or less round-trip.

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Traveling to a place near Chicago?

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

More options for your flight to Chicago