Cheap flights from Chicago to Cancún
The cheapest round trip from Chicago to Cancún that travelers found recently is $409 with a carry-on: a $329 fare on Volaris plus about $80 for a carry-on both ways. It leaves Wed, Jan 27 and comes back Sun, Jan 31.
Live prices for Wed, Jan 27 to Sun, Jan 31
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Wed, Jan 27 | Sun, Jan 31 | Volaris | ORD → CUN | 1 stop | $329 | +$80 | $409 | Live price |
| Wed, Feb 17 | Mon, Feb 22 | Volaris | ORD → CUN | 1 stop | $331 | +$80 | $411 | Live price |
| Wed, Jan 20 | Wed, Feb 3 | Volaris | ORD → CUN | 1 stop | $355 | +$80 | $435 | Live price |
| Fri, Nov 13 | Wed, Nov 25 | United | ORD → CUN | 1 stop | $436 | Included | $436 | Live price |
| Tue, Jan 19 | Tue, Feb 2 | Volaris | ORD → CUN | 1 stop | $357 | +$80 | $437 | Live price |
| Mon, Nov 16 | Mon, Nov 23 | Frontier | ORD → CUN | Nonstop | $337 | +$110 | $447 | Live price |
| Fri, Nov 13 | Fri, Nov 20 | Frontier | ORD → CUN | Nonstop | $342 | +$110 | $452 | Live price |
| Fri, Nov 13 | Mon, Nov 16 | United | ORD → CUN | 1 stop | $464 | Included | $464 | Live price |
| Sat, Nov 14 | Thu, Nov 26 | Volaris | ORD → CUN | 1 stop | $385 | +$80 | $465 | Live price |
| Sat, Mar 27 | Thu, Apr 1 | Viva Aerobus | ORD → CUN | 1 stop | $390 | +$80 | $470 | Live price |
Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast: check the live price before you book.
Cheapest month to fly
| Month | Cheapest trip | From | Live prices |
|---|---|---|---|
| November 2026 | Fri, Nov 13 to Wed, Nov 25, 12 nights | $436 | Live price |
| December 2026 | Thu, Dec 24 to Wed, Jan 6, 13 nights | $539 | Live price |
| January 2027 | Wed, Jan 27 to Sun, Jan 31, 4 nights | $409 | Live price |
| February 2027 | Wed, Feb 17 to Mon, Feb 22, 5 nights | $411 | Live price |
| March 2027 | Sat, Mar 27 to Thu, Apr 1, 5 nights | $470 | Live price |
| April 2027 | Sat, Apr 10 to Sat, Apr 17, 7 nights | $470 | Live price |
Bag fees on this route
What the airlines flying Chicago to Cancún usually charge for one bag each way. Budget airlines often sell the cheapest fares and charge the most for bags, so compare the total, not the fare.
| Airline | Carry-on, each way | Checked bag, each way |
|---|---|---|
| Air Canada | Included | $40 |
| Frontier | $55 | $50 |
| Southwest | Included | $35 |
| United | Included | $40 |
| Viva Aerobus | $40 | $40 |
| Volaris | $40 | $40 |
Our estimates: fees depend on the fare type and when you pay. Check the airline's own price when you book.
How these prices work
These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).
Not sure where to go? Tell Dipt your budget and vibe and it finds the trip.
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