Chicago to Cancun flights
The cheapest round trip we found from Chicago to Cancun is $205 (Jan 14 – 19, 2027, 1 stop), 48% below the usual $394.
CHI to CUN · Round trip · Economy · Prices per person in USD · Price found (1 day ago)
Cheapest found
Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| November 2026 | $446 |
| December 2026 | $767 |
| January 2027 | $205 (cheapest month) |
| February 2027 | $394 |
| March 2027 | $422 |
| April 2027 | $392 |
Cheapest dates in the next 4 months
Round trip, per person-
Jan 14 – 19, 2027 5 nights · leave Thu$205 −48% vs usual$205 −48% vs usual Book
Frontier Airlines 1 stop · 5h 24m -
Jan 26 – Feb 3, 2027 8 nights · leave Tue$251 −36% vs usual$251 −36% vs usual Book
Air Canada 1 stop · 7h 02m -
Nov 4 – 7 3 nights · leave Wed$446 +13% vs usual$446 +13% vs usual Book
Air Canada 1 stop · 7h 12m
-
Nov 15 – 22 7 nights · leave Sun$460 +17% vs usual$460 +17% vs usual Book
Frontier Airlines 1 stop · 5h 20m
-
Nov 18 – 27 9 nights · leave Wed$476 +21% vs usual$476 +21% vs usual Book
Air Canada 1 stop · 6h 02m
-
Dec 27 – Jan 3, 2027 7 nights · leave Sun$767 +95% vs usual$767 +95% vs usual Book
Frontier Airlines 1 stop · 5h 34m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Things to do in Cancun
One Go City pass for Chichen Itza day trip, Xcaret Park, Interactive Aquarium Cancun and more
- All-Inclusive Pass Unlimited Visit as many attractions as you like for 2–5 days from $189 See pass
- All-Inclusive Pass Plus All-Inclusive plus 1 extra attractions from $274 See pass
- Essentials Pass A few top attractions, chosen as you go from $159 See pass
Go City prices checked Oct 23, 2026; the final price is on Go City. Partner links: we may earn a commission if you book, at no extra cost to you.
Plan the rest of your trip
Cancun · Jan 14 – 19, 2027- eSIM for Mexico Yesim · prepaid mobile data (opens Yesim in a new tab)
- Car rental in Mexico Economybookings · compare rental companies (opens Economybookings in a new tab)
Partner links: we may earn a commission if you book, at no extra cost to you.
Good to know
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Flights to Cancun from other cities
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- Tijuana $190
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Chicago to Cancun: questions
How much does a flight from Chicago to Cancun cost?
The cheapest round trip we have found right now is $205, leaving January 14 and returning January 19. The usual price on this route is about $394, so this fare is 48% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from Chicago to Cancun?
January 2027, with round trips from $205. The most expensive month in our data is December (from $767). Based on the 6 months ahead we have prices for.
Which airports do Chicago to Cancun flights use?
Chicago airports include O'Hare International (ORD), Chicago Midway International (MDW) and Chicago Rockford International (RFD). Cancun airports include Cancun International (CUN). The prices on this page cover every airport in both cities (CHI and CUN are the city codes).
About this route
We track round-trip economy fares from Chicago (United States) to Cancun (Mexico) using Travelpayouts / Aviasales data. The cheapest round trip we've found is $205, departing January 14 and returning January 19, about 48% below the usual $394. Right now we're following 6 upcoming date combinations on this route. The cheapest month to fly in our data is January, from $205. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.