Cheap flights from Chicago to Cancun

One-way fares from $122 · CHI → CUN · prices found by travellers in the last 48 hours

Compare all dates Cancun → Chicago
Cheapest fare
$122

Viva Aerobus · Mon, Apr 5

Cheapest month
April

from $122

Direct flights
Not recently

Usually 1+ stop

Quickest trip
5h 44m

2,310 km

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Cheapest month to fly from Chicago to Cancun

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 $197
  2. December 2026 $222
  3. February 2027 $130
  4. April 2027 Cheapest $122

Cheapest dates in April 2027

The lowest fares we've seen for each day, cheapest first.

Viva Aerobus
Depart02:05 Thu, Apr 1ORD → CUN 6h 07m · 1 stop
$122one way, per person
View deal
Viva Aerobus
Depart02:05 Sat, Apr 3ORD → CUN 6h 02m · 1 stop
$122one way, per person
View deal
Viva Aerobus
Depart02:05 Mon, Apr 5ORD → CUN 6h 02m · 1 stop
$122one way, per person
View deal
Viva Aerobus
Depart12:20 Fri, Apr 2ORD → CUN 7h 12m · 1 stop
$133one way, per person
View deal
Viva Aerobus
Depart12:20 Sun, Apr 4ORD → CUN 7h 12m · 1 stop
$133one way, per person
View deal
See every date in April 2027 →

Plan the rest of your trip to Cancun

Where to stay, what to do and getting around, from our travel partners.

Where to stay

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Things to do

Things to do in CancunTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in CancunPre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in CancunCompare rental cars from major brands on EconomyBookings Compare cars →

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About flights from Chicago to Cancun

Chicago (CHI) and Cancun (CUN) are about 2,310 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 5h 44m. Over the next few months, one-way fares start from $122, and April 2027 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Chicago to Cancun?

The cheapest one-way fare we've seen recently is $122 with Viva Aerobus, departing Monday, April 5, 2027. Over the coming months, the lowest fare in each month ranges from $122 to $222.

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

April 2027 currently has the lowest fares, from $122 one way.

Are there direct flights from Chicago to Cancun?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from Chicago to Cancun?

The quickest journey we've seen takes about 5h 44m. Chicago and Cancun are around 2,310 km apart.

Which airlines fly from Chicago to Cancun?

Recent fares on this route were with Viva Aerobus and Frontier Airlines.

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