
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $227 (CheapOair) |
One-way from | $100 (Cheapflightsfares) |
Popular in | December |
Cheapest in | September |
Average price | $388 |
Good round-trip deal | $320 or less |
Good one-way deal | $136 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
seg 3/9
8:05 am-11:50 am
Nonstop3h 45m
Cancun
sex 3/13
8:30 am-12:10 pm
Nonstop3h 40m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
seg 2/9
10:35 am-3:15 pm
Nonstop3h 40m
Cancun
qui 2/12
3:40 pm-6:20 pm
Nonstop3h 40m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
qua 3/11
7:10 am-8:20 pm
2 stops13h 10m
Cancun
sáb 3/14
6:01 am-1:45 pm
1 stop7h 44m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
qua 3/11
9:50 am-8:20 pm
2 stops10h 30m
Cancun
qua 3/18
6:01 am-1:45 pm
1 stop7h 44m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
qui 3/5
6:30 am-9:11 pm
2 stops13h 41m
Cancun
qui 3/12
7:01 am-12:13 am
1 stop17h 12m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
seg 3/2
6:30 am-9:11 pm
2 stops13h 41m
Cancun
qui 3/5
6:01 am-12:55 pm
1 stop7h 54m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
dom 2/22
1:11 am-6:47 pm
1 stop16h 36m
Cancun
qua 3/4
8:38 am-11:56 pm
2 stops16h 18m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
seg 3/9
10:45 am-8:20 pm
1 stop9h 35m
Cancun
qua 3/11
8:00 am-5:22 pm
1 stop9h 22m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
seg 2/9
12:46 pm-9:11 pm
1 stop7h 25m
Cancun
qui 2/12
4:45 pm-10:31 pm
1 stop6h 46m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
ter 3/10
6:00 am-3:45 pm
1 stop9h 45m
Cancun
qui 3/12
10:50 am-5:54 pm
1 stop7h 04m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
Booking 66 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Cancún. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, January is the cheapest month in which you can book a flight from Chicago to Cancún (average of $148). Flying from Chicago to Cancún in July is currently the most expensive (average of $217). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
It’s optimal to fly from Chicago to Cancún in the morning. By choosing this option you can save up to 27% on the cost of your flight, compared to a flight at noon.
The most flights from CHI to CUN are scheduled on a Monday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (11 on average).
Atlanta (ATL) – chosen by Cheapflights users on 56% of 1-stop itineraries from Chicago to Cancún on Cheapflights.
Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $354.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 6h 34m.
Flights via Mexico City (MEX) offer the fastest connection on this route, with an average layover time of 1h 48m.
About 15% of weekly flights between Chicago and Cancún have experienced delays in the past year, with the average delay time being 146 minutes.
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
Tuesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Spirit Airlines have had the lowest number of delays on this route, with just 12% of flights being delayed.
Crew
Comfort
Food
Boarding
Overall
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Comfort
Food
Boarding
Overall
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Comfort
Food
Boarding
Overall
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Comfort
Food
Boarding
Overall
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Comfort
Food
Boarding
Overall
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Comfort
Food
Boarding
Overall
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$126 | Average$346 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$135 | Average$336 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$140 | Average$370 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$166 | Average$1,995 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$183 | Average$415 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$220 | Average$343 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$250 | Average$425 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$265 | Average$516 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$522 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$279 | Average$387 | FlexibilityNo cancel fee | On-time67% |