Chicago to Cancun MDW, ORD, RFD → CUN
Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD) → Cancun International Airport (CUN)
The cheapest return found recently is $442 with Volaris, 13 Jan 2027 – 24 Jan 2027, found today.
Return
The cheapest return fare on each of 12 departure dates is usually $361 to $459.
Cheapest return found recently
$442
13 Jan 2027 – 24 Jan 2027 · Volaris
O'Hare International Airport (ORD) → Cancun International Airport (CUN)
Leaves 6:29 a.m. · Return leaves 2:45 p.m. · 23 h 18 min of travel, both ways together
out 1 stop, back 1 stop
found today
Cheapest nonstop return
$363
31 Oct – 21 Nov · Frontier Airlines
O'Hare International Airport (ORD) → Cancun International Airport (CUN)
Leaves 6:10 a.m. · Return leaves 11:24 a.m. · 7 h 59 min of travel, both ways together
out nonstop, back nonstop
found 4 days ago
Found recently, and the cheapest we hold
$442 13 Jan 2027 – 24 Jan 2027found todaySee prices for these dates
$329 27 Jan 2027 – 31 Jan 2027found 6 days agoSee prices for these dates
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest return we saw each day was $282 to $388.
At $442, the cheapest return found recently is above that range.
25 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 12 departure dates from 22 Oct to 27 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 11-night return fares leaving within 3 days of 13 Jan 2027 to compare.
Every date we hold
28 fares on 12 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 22 Oct – 29 Oct | $742 | Allegiant Air | Chicago Rockford International Airport (RFD) → Cancun International Airport (CUN) | out 2 stops, back 1 stop | found 4 days ago | See prices for these dates |
| 30 Oct – 4 Nov | $606 | Allegiant Air | Chicago Rockford International Airport (RFD) → Cancun International Airport (CUN) | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| 31 Oct – 21 Nov | $363 | Frontier Airlines | O'Hare International Airport (ORD) → Cancun International Airport (CUN) | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| 10 Nov – 26 Dec | $435 | Volaris | O'Hare International Airport (ORD) → Cancun International Airport (CUN) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| 12 Nov – 19 Nov | $407 | Volaris | O'Hare International Airport (ORD) → Cancun International Airport (CUN) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| 13 Nov – 20 Nov | $342 | Frontier Airlines | O'Hare International Airport (ORD) → Cancun International Airport (CUN) | out nonstop, back nonstop | found 5 days ago | See prices for these dates |
| 14 Nov – 26 Nov | $385 | Volaris | O'Hare International Airport (ORD) → Cancun International Airport (CUN) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| 18 Nov – 27 Nov | $470 | Air Canada | O'Hare International Airport (ORD) → Cancun International Airport (CUN) | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| 11 Dec – 26 Dec | $455 | American Airlines | O'Hare International Airport (ORD) → Cancun International Airport (CUN) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| 13 Jan 2027 – 24 Jan 2027 | $442 | Volaris | O'Hare International Airport (ORD) → Cancun International Airport (CUN) | out 1 stop, back 1 stop | found today | See prices for these dates |
| 20 Jan 2027 – 3 Feb 2027 | $355 | Volaris | O'Hare International Airport (ORD) → Cancun International Airport (CUN) | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| 27 Jan 2027 – 31 Jan 2027 | $329 | Volaris | O'Hare International Airport (ORD) → Cancun International Airport (CUN) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
Which month looks cheapest?
January 2027 is the cheapest month — from $329.
Airlines on the cheapest dates: Volaris, Allegiant Air, Frontier Airlines, Air Canada, American Airlines.
Premium cabin fares from Chicago to Cancun
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 13 Jan 2027 – 24 Jan 2027 in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Chicago to Cancun?
Return
Fares 90 to 179 days before departure were typically 31% lower than 0 to 6 days before departure.
From the cheapest return each day between 24 Sept and 18 Oct (25 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 |
|---|---|---|---|---|
| 0–6 days | $428 | $426 | +44% | 17 |
| 7–13 days | $446 | $363 | +50% | 16 |
| 14–29 days | $394 | $342 | +33% | 19 |
| 30–59 days | $344 | $308 | +16% | 25 |
| 60–89 days | $385 | $294 | +30% | 24 |
| 90–179 days | $297 | $282 | Cheapest seen | 25 |
| 180+ days | $388 | $388 | +31% | 19 |
Live price for these dates
The cheapest return found recently is for 13 Jan 2027 – 24 Jan 2027. A live search on this page shows what those dates cost now, for one adult in economy.
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