Cheap flights from Chicago to Havana from $802 MDW, ORD → HAV
Chicago Midway International Airport (MDW), O'Hare International Airport (ORD) → Jose Marti International Airport (HAV)
The cheapest return found recently is $802 with Copa Airlines, 31 Dec – 11 Jan 2027, found yesterday.
- Cheapest return found recently
- $802, 31 Dec to 11 Jan 2027
- Usual return price
- $897 to $994
Return
The cheapest return fare on each of 3 departure dates is usually $897 to $994.
Cheapest return found recently
$802
31 Dec – 11 Jan 2027 · Copa Airlines
O'Hare International Airport (ORD) → Jose Marti International Airport (HAV)
Leaves 2:17 p.m. · Return leaves 4:19 a.m. · 29 h 36 min of travel, both ways together
out 1 stop, back 1 stop
found yesterday
Cheapest nonstop return
None seen yet.
Found recently, and the cheapest we hold
$802 31 Dec – 11 Jan 2027found yesterdaySee prices for these dates
It is also the cheapest return we hold, of any age.
What have prices looked like?
Over 28 days, 25 Sept to 26 Oct, the cheapest return we saw each day was $515 to $1,207.
28 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?
Compared with the cheapest return fare on each of 3 departure dates from 27 Dec to 31 Dec, 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?
No. We hold 11-night return fares on 1 other departure date within 3 days of 31 Dec, and it is not cheaper.
Every date we hold
3 fares on 3 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 27 Dec – 8 Jan 2027 | $992 | Southwest Airlines | Chicago Midway International Airport (MDW) → Jose Marti International Airport (HAV) | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| 30 Dec – 10 Jan 2027 | $996 | Southwest Airlines | Chicago Midway International Airport (MDW) → Jose Marti International Airport (HAV) | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| 31 Dec – 11 Jan 2027 | $802 | Copa Airlines | O'Hare International Airport (ORD) → Jose Marti International Airport (HAV) | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
Airlines on the cheapest dates: Southwest Airlines, Copa Airlines.
Premium cabin fares from Chicago to Havana
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 31 Dec – 11 Jan 2027 in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Chicago to Havana?
Return
The cheapest fares were 30 to 59 days before departure.
From the cheapest return each day between 25 Sept and 26 Oct (28 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.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 14–29 days | $532 | $532 | +3% | 8 |
| 30–59 days | $515 | $515 | Cheapest seen | 15 |
| 60–89 days | $942 | $942 | +83% | 13 |
Live price for these dates
The cheapest return found recently is for 31 Dec – 11 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 Chicago to Havana?
The cheapest return found recently is $802 with Copa Airlines, 31 Dec to 11 Jan 2027, found yesterday. The cheapest return fare on each of 3 departure dates is usually $897 to $994.
How far ahead should I book a flight from Chicago to Havana?
In 28 days of prices between 25 Sept and 26 Oct, return fares were cheapest 30 to 59 days before departure.
Which airlines have the cheapest flights from Chicago to Havana?
Between 27 Dec and 31 Dec, Southwest Airlines has the cheapest return on 2 of the 3 departure dates we hold, and Copa 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