$185 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, Oct 21 - Wed, Nov 4
Copa Airlines Logo
6:05 pm - 12:57 amSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
29h 52m1 stop Panama City Tocumen Intl
Copa Airlines Logo
2:13 pm - 9:07 amORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
18h 54m1 stop Panama City Tocumen Intl
$365Copa Airlines
Wed, Jan 27 - Sun, Jan 31
United Airlines Logo
1:25 pm - 6:57 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
5h 32mnonstop
United Airlines Logo
6:50 am - 6:16 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
11h 26m1 stop Houston George Bush Intcntl
$365United Airlines
Wed, Nov 11 - Wed, Nov 18
Air Canada Logo
3:10 pm - 1:13 pmLIR  Liberia-ORD Chicago O'Hare Intl
22h 03m1 stop Toronto Pearson Intl
Air Canada Logo
12:50 pm - 2:10 pmORD  Chicago O'Hare Intl-LIR Liberia
25h 20m1 stop Toronto Pearson Intl
$365Air Canada
Fri, Jan 22 - Fri, Jan 29
Avianca Logo
5:35 am - 12:55 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
7h 20m1 stop Guatemala City La Aurora
Avianca Logo
2:20 pm - 11:15 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
8h 55m1 stop Guatemala City La Aurora
$366Avianca
Tue, Jan 19 - Tue, Jan 26
Avianca Logo
1:55 am - 8:30 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
18h 35m1 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
$366Avianca
Fri, Jan 15 - Sat, Jan 23
United Airlines Logo
1:15 am - 10:59 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
21h 44m1 stop Houston George Bush Intcntl
United Airlines Logo
10:30 am - 1:00 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
26h 30m1 stop Washington, D.C. Dulles Intl
$366United Airlines
Sun, Nov 8 - Fri, Nov 13
Copa Airlines Logo
10:03 am - 12:11 amSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
14h 08m1 stop Panama City Tocumen Intl
Copa Airlines Logo
2:13 pm - 10:59 amORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
20h 46m1 stop Panama City Tocumen Intl
$366Copa Airlines
Sun, Nov 22 - Sat, Dec 5
Delta Logo
2:37 pm - 11:54 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
9h 17m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:49 am - 10:17 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
15h 28m1 stop Atlanta Hartsfield-Jackson
$366Delta
Wed, Oct 21 - Sat, Nov 7
American Airlines Logo
6:00 am - 8:06 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
13h 06m2 stops Miami Washington, D.C. Reagan-National
American Airlines Logo
8:45 am - 8:50 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
12h 05m2 stops Washington, D.C. Reagan-National Miami
$380American Airlines
Tue, Oct 27 - Fri, Nov 6
American Airlines Logo
6:00 am - 8:17 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
13h 17m2 stops Miami Austin Bergstrom
American Airlines Logo
9:06 pm - 1:07 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
16h 01m1 stop Charlotte Douglas
$380American 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 $378. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $584 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 October with an average price of $263.

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 morning, when round-trip flights cost $461 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $464.

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 $283 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 3 weeks before departure, which saves you about 9% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Find deals

Good to know

Low season

June

Cheapest flight

$185
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from San José to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • 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 $484. The cheapest price found on KAYAK in the last 2 weeks cost $214 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 28,193 direct flights from within Costa Rica to Chicago O'Hare Intl Airport. The most common day for departures is Sunday, with 16% 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 $329, from San José $360
  • 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
Gurnee
South Haven
Oak Brook
Tinley Park
Hammond
Saint Joseph
Des Plaines
Elk Grove Village
Hoffman Estates
Portage
South Holland
Oakbrook Terrace
Willowbrook
Lansing
Alsip
Delavan
Lisle
Northbrook
Valparaiso

More options for your flight to Chicago