Cheap flights from Chicago to San Jose, Costa Rica from $237 MDW, ORD, RFD → SJO

Found recently, and the cheapest we hold

It is also the cheapest return we hold, of any age.

What have prices looked like?

Over 47 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $291 to $483.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other 6-night return fares leaving within 3 days of 5 Jan 2027 to compare.

Every date we hold

34 fares on 4 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $438.

Found recently, and the cheapest we hold

It is also the cheapest one-way we hold, of any age.

What have prices looked like?

Over 10 days, 27 Sept to 11 Nov, the cheapest one-way we saw each day was $237 to $715.

At $237, the cheapest one-way found recently is at the low end of that range.

10 days is a short history, so treat this range as an early guide.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

No. We hold one-way fares on 1 other departure date within 3 days of 5 Jan 2027, and it is not cheaper.

Every date we hold

14 fares on 3 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $237.

Return

Fares 60 to 89 days before departure were typically 14% lower than 7 to 13 days before departure.

From the cheapest return each day between 24 Sept and 11 Nov (47 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

One-way

Not enough history yet: in 10 days of one-way prices, 27 Sept to 11 Nov, fewer than 3 booking ranges had prices on 7 days or more.

How much is a return flight from Chicago to San Jose?

The cheapest return found recently is $438 with avianca airlines, 5 Jan 2027 to 11 Jan 2027, found 3 days ago. The cheapest return fare on each of 4 departure dates is usually $707 to $945.

How much is a one-way flight from Chicago to San Jose?

The cheapest one-way found recently is $237 with Volaris, 5 Jan 2027, found 3 days ago. The cheapest one-way fare on each of 3 departure dates is usually $258 to $293.

What is the cheapest month to fly from Chicago to San Jose?

January 2027 is the cheapest month for a return, from $438, 5 Jan 2027 to 11 Jan 2027, found 3 days ago. It is the cheapest month for a one-way too, from $237, 5 Jan 2027, found 3 days ago.

How far ahead should I book a flight from Chicago to San Jose?

In 47 days of prices between 24 Sept and 11 Nov, return fares 60 to 89 days before departure were typically 14% lower than 7 to 13 days before departure.

Is there a direct flight from Chicago to San Jose?

Yes, the cheapest nonstop return found recently is $975 with United Airlines, 5 Jan 2027 to 11 Jan 2027, found 3 days ago. The cheapest nonstop one-way found recently is $452 with United Airlines, 5 Jan 2027, found 3 days ago.

How long is the flight from Chicago to San Jose?

The cheapest nonstop one-way found recently, with United Airlines on 5 Jan 2027, takes 5 h 13 min from O'Hare International Airport (ORD) to Juan Santamaria International Airport (SJO). The cheapest one-way found recently, with Volaris on 5 Jan 2027, takes 9 h 51 min with 1 stop.

Which airlines have the cheapest flights from Chicago to San Jose?

Between 27 Dec and 15 Mar 2027, Frontier Airlines has the cheapest return on 1 of the 4 departure dates we hold, Copa Airlines on 1 and avianca airlines on 1. Between 28 Dec and 8 Jan 2027, Frontier Airlines has the cheapest one-way on 2 of the 3 departure dates we hold, and Volaris on 1.