$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 flight to Chicago?

In the last 5 days, the cheapest flight deal to Chicago was found on the route from Liberia, at $323 return. The most popular connection is from San José to Chicago and KAYAK users have found round-trip deals for as low as $383 in the last 5 days.

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 O'Hare Intl Airport?

The cheapest month for flights to Chicago O'Hare Intl Airport is February, where tickets cost $393 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 $643 and $559 respectively. For one-way flights, the best month to travel is February with an average price of $353.

What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the afternoon, when round-trip flights cost $470 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport?

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

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.

Good to know

Low season

June

Cheapest flight

$202
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Liberia to Chicago

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 5 days, the cheapest flight deal to Chicago was found on the route from Liberia, at $323 return. The most popular connection is from San José to Chicago and KAYAK users have found round-trip deals for as low as $383 in the last 5 days.

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    The distance between Chicago O'Hare Intl Airport and downtown Chicago is 16 miles.

  • 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 O'Hare Intl Airport are there each week?

    Each week there are around 41,811 direct flights from within Costa Rica to Chicago O'Hare Intl Airport. 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 cheap airfare to Chicago? 25% of our users found round-trip tickets to Chicago for the following prices or less: From Liberia $276, from San José $408

  • 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
Gurnee
Merrillville
South Haven
Oak Brook
Tinley Park
Hammond
Saint Joseph
Des Plaines
Elk Grove Village
Hoffman Estates
Oakbrook Terrace
Portage
South Holland
Willowbrook
Lansing
Lisle
Alsip
Valparaiso
Northbrook
Delavan

More options for your flight to Chicago