Cheap flights from San Jose, Costa Rica to Chicago from $439 SJO → MDW, ORD
Juan Santamaria International Airport (SJO) → Chicago Midway International Airport (MDW), O'Hare International Airport (ORD)
The cheapest return found recently is $535 with avianca airlines, 28 Dec – 3 Jan 2027, found 5 days ago. The cheapest one-way found recently is $439 with Frontier Airlines, 4 Jan 2027, found 5 days ago.
- Cheapest one-way found recently
- $439, found 5 days ago
- Cheapest return found recently
- $535, 28 Dec to 3 Jan 2027
- Cheapest month to fly
- December 2026, one-way fares from $305 found in the last 7 days
Return
Not enough comparable prices yet for a usual return price.
Cheapest return found recently
$535
28 Dec – 3 Jan 2027 · avianca airlines
Juan Santamaria International Airport (SJO) → O'Hare International Airport (ORD)
Leaves 4:15 p.m. · Return leaves 2:20 p.m. · 38 h 55 min of travel, both ways together
out 1 stop, back 1 stop
found 5 days ago
Cheapest nonstop return
None seen yet.
Found recently, and the cheapest we hold
$535 28 Dec – 3 Jan 2027found 5 days agoSee prices for these dates
It is also the cheapest return we hold, of any age.
What have prices looked like?
Over 23 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $256 to $535.
At $535, the cheapest return found recently is at the high end of that range.
23 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good return price?
Not enough comparable prices yet: we hold return fares on 1 departure date and need at least 3 to say what is usual.
Could nearby dates be cheaper?
We hold no other 6-night return fares leaving within 3 days of 28 Dec to compare.
Every date we hold
1 fares on 1 departure dates
See every date as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 28 Dec – 3 Jan 2027 | $535 | avianca airlines | Juan Santamaria International Airport (SJO) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
Airlines on the cheapest dates: avianca airlines.
One-way
The cheapest one-way fare on each of 3 departure dates is usually $325 to $392.
Cheapest one-way found recently
$439
4 Jan 2027 · Frontier Airlines
Juan Santamaria International Airport (SJO) → Chicago Midway International Airport (MDW)
Leaves 1:31 p.m. · 27 h 15 min trip
1 stop
found 5 days ago
Cheapest nonstop one-way
None seen yet.
Found recently, and the cheapest we hold
$439 4 Jan 2027found 5 days agoOpen this trip
$305 24 Decfound 7 days agoOpen this trip
What have prices looked like?
Over 10 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $305 to $468.
10 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good one-way price?
Compared with the cheapest one-way fare on each of 3 departure dates from 19 Dec to 4 Jan 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other one-way fares leaving within 3 days of 4 Jan 2027 to compare.
Every date we hold
3 fares on 3 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 19 Dec | $345 | Southwest Airlines | Juan Santamaria International Airport (SJO) → Chicago Midway International Airport (MDW) | 1 stop | found 7 days ago | Open this trip |
| 24 Dec | $305 | jetBlue | Juan Santamaria International Airport (SJO) → O'Hare International Airport (ORD) | 1 stop | found 7 days ago | Open this trip |
| 4 Jan 2027 | $439 | Frontier Airlines | Juan Santamaria International Airport (SJO) → Chicago Midway International Airport (MDW) | 1 stop | found 5 days ago | Open this trip |
Which month looks cheapest?
December 2026 is the cheapest month — from $305.
Airlines on the cheapest dates: Southwest Airlines, jetBlue, Frontier Airlines.
Premium cabin fares from San Jose to Chicago
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 28 Dec – 3 Jan 2027 in another cabin: Premium economy · Business · First
Today's prices for 4 Jan 2027 in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for San Jose to Chicago?
Return
Not enough history yet: in 23 days of return prices, 24 Sept to 11 Nov, fewer than 3 booking ranges had prices on 7 days or more.
One-way
Not enough history yet: in 10 days of one-way prices, 24 Sept to 11 Nov, fewer than 3 booking ranges had prices on 7 days or more.
Live price for these dates
The cheapest return found recently is for 28 Dec – 3 Jan 2027. A live search on this page shows what those dates cost now, for one adult in economy.
Questions about this trip
How much is a return flight from San Jose to Chicago?
The cheapest return found recently is $535 with avianca airlines, 28 Dec to 3 Jan 2027, found 5 days ago.
How much is a one-way flight from San Jose to Chicago?
The cheapest one-way found recently is $439 with Frontier Airlines, 4 Jan 2027, found 5 days ago. The cheapest one-way we hold, of any age, is $305 with jetBlue, 24 Dec, found 7 days ago. The cheapest one-way fare on each of 3 departure dates is usually $325 to $392.
What is the cheapest month to fly from San Jose to Chicago?
December 2026 is the cheapest month for a one-way, from $305, 24 Dec, found 7 days ago.
How long is the flight from San Jose to Chicago?
The cheapest one-way found recently, with Frontier Airlines on 4 Jan 2027, takes 27 h 15 min with 1 stop.
Which airlines have the cheapest flights from San Jose to Chicago?
Between 19 Dec and 4 Jan 2027, Southwest Airlines has the cheapest one-way on 1 of the 3 departure dates we hold, jetBlue on 1 and Frontier Airlines on 1.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work