Cheap flights from Chicago to Cancun from $122 MDW, ORD, RFD → CUN

Found recently, and the cheapest we hold

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $251 to $388.

At $399, the cheapest return found recently is above that range.

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

Could nearby dates be cheaper?

We hold no other 14-night return fares leaving within 3 days of 3 Apr 2027 to compare.

Every date we hold

89 fares on 11 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $330.

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 46 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $122 to $192.

At $122, the cheapest one-way found recently is at the low end of that range.

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

Could nearby dates be cheaper?

No. We hold one-way fares on 3 other departure dates within 3 days of 1 Apr 2027, and none is cheaper.

Every date we hold

19 fares on 6 departure dates

Which month looks cheapest?

April 2027 is the cheapest month — from $122.

Return

Fares 90 to 179 days before departure were typically 30% lower than 0 to 6 days before departure.

From the cheapest return each day between 24 Sept and 11 Nov (49 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

Fares 90 to 179 days before departure were typically 14% lower than 30 to 59 days before departure.

From the cheapest one-way each day between 24 Sept and 11 Nov (46 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.

How much is a return flight from Chicago to Cancun?

The cheapest return found recently is $399 with Viva Aerobus, 3 Apr 2027 to 17 Apr 2027, found 2 days ago. The cheapest return we hold, of any age, is $330 with Volaris, 20 Jan 2027 to 30 Jan 2027, found 3 days ago. The cheapest return fare on each of 11 departure dates is usually $404 to $468.

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

The cheapest one-way found recently is $122 with Viva Aerobus, 1 Apr 2027, found 4 days ago. The cheapest one-way fare on each of 6 departure dates is usually $122 to $133.

What is the cheapest month to fly from Chicago to Cancun?

January 2027 is the cheapest month for a return, from $330, 20 Jan 2027 to 30 Jan 2027, found 3 days ago. April 2027 is the cheapest month for a one-way, from $122, 1 Apr 2027, found 4 days ago.

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

In 49 days of prices between 24 Sept and 11 Nov, return fares 90 to 179 days before departure were typically 30% lower than 0 to 6 days before departure. In 46 days of prices between 24 Sept and 11 Nov, one-way fares 90 to 179 days before departure were typically 14% lower than 30 to 59 days before departure.

Is there a direct flight from Chicago to Cancun?

Yes, the cheapest nonstop return found recently is $627 with Frontier Airlines, 11 Mar 2027 to 18 Mar 2027, found 2 days ago.

How long is the flight from Chicago to Cancun?

The cheapest one-way found recently, with Viva Aerobus on 1 Apr 2027, takes 12 h 45 min with 1 stop.

Which airlines have the cheapest flights from Chicago to Cancun?

Between 15 Nov and 25 Aug 2027, Volaris has the cheapest return on 6 of the 11 departure dates we hold, Air Canada on 3 and Viva Aerobus on 2. Between 1 Apr 2027 and 8 Sept 2027, Viva Aerobus has the cheapest one-way on 5 of the 6 departure dates we hold, and Aeromexico on 1.