The cheapest one-way ticket from Chicago to Cancun found recently is 110€, on 1 Apr (April 2027, one stop). The most expensive month is September 2027, from 227€. Round trips start at 298€, in January 2027. No direct flights were seen lately; the quickest connection takes 5h 44m. Airlines on this route: Viva Aerobus, Frontier Airlines, Aeromexico, Volaris, Air Canada.
Lowest fare by month
| Month | One way | Round trip |
|---|---|---|
| November 2026 | 176€10 Nov · 1 stop | 369€17 Nov–22 Nov · 1 stop |
| December 2026 | 199€21 Dec · 1 stop | 387€5 Dec–8 Dec · 1 stop |
| January 2027 | — | 298€26 Jan–3 Feb · 1 stop |
| February 2027 | 116€8 Feb · 1 stop | 351€8 Feb–14 Feb · 1 stop |
| March 2027 | — | 414€13 Mar–20 Mar · 1 stop |
| April 2027 | 110€1 Apr · 1 stop | 322€11 Apr–18 Apr · 1 stop |
| September 2027 | 227€8 Sept · 1 stop | — |
Cheapest days in April 2027
One way, per adult. Blank days: nobody searched them lately.
At a glance
- Airports
- MDW · DPA · PWK · ORD · RFD → CUN
- Airlines
- Viva Aerobus, Frontier Airlines, Aeromexico, Volaris, Air Canada
- Direct flights
- No direct fares seen lately
The rest of the trip to Cancun
- Internet when you land ↗An eSIM for the country, set up before you fly. Handy outside the EU, or when roaming costs extra.
- A ride from the airport ↗A driver waiting at arrivals, at a fixed price.
- Things to do in Cancun ↗Tickets for museums, tours and sights.
Flight delayed by three hours or more, or cancelled? Under EU rules you may be owed up to €600. Check your claim.
Frequently asked questions
How much is a flight from Chicago to Cancun?
The cheapest one-way ticket found recently is 110€, in April 2027. A round trip starts at 298€. Fares are per adult and change often.
What is the cheapest month to fly from Chicago to Cancun?
April 2027, from 110€ one way. The most expensive is September 2027, from 227€.
Are there direct flights from Chicago to Cancun?
No direct fares were seen in recent days, only connections.
How long is the flight from Chicago to Cancun?
The shortest flight found takes 5h 44m, with a stop.
Which airlines fly from Chicago to Cancun?
Viva Aerobus, Frontier Airlines, Aeromexico, Volaris, Air Canada.
Which airports do flights from Chicago to Cancun use?
They leave from MDW, DPA, PWK, ORD, RFD and land at CUN.
Want to know when it gets cheaper?
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Watch this routeFares are the lowest travellers found in recent days' searches, per adult. They change: check the price before you book. Booking links go to our travel partner and are affiliate links: if you book through them we earn a small commission, at no cost to you.