
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $254 (CheapOair) |
One-way from | $98 (Frontier) |
Popular in | December |
Cheapest in | September |
Average price | $523 |
Good round-trip deal | $369 or less |
Good one-way deal | $160 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sun 5/17
6:24 am-6:35 pm
2 stops12h 11m
Cancun
Wed 5/20
1:45 pm-8:26 pm
1 stop6h 41m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Wed 4/29
7:00 am-2:10 pm
1 stop7h 10m
Cancun
Wed 5/6
3:15 pm-6:55 pm
Nonstop3h 40m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sun 5/3
5:15 am-12:40 pm
1 stop7h 25m
Cancun
Wed 5/6
8:00 am-8:40 pm
2 stops12h 40m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Mon 4/13
5:15 am-4:38 pm
2 stops11h 23m
Cancun
Fri 4/17
3:15 pm-11:59 pm
1 stop8h 44m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 6/12
1:15 pm-8:23 pm
1 stop7h 08m
Cancun
Fri 6/26
8:00 am-8:18 pm
1 stop12h 18m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 4/10
6:15 am-1:00 pm
1 stop6h 45m
Cancun
Fri 4/17
12:25 pm-11:59 pm
2 stops11h 34m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Thu 4/9
5:30 am-4:38 pm
2 stops11h 08m
Cancun
Tue 5/5
8:00 am-6:52 pm
2 stops10h 52m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 5/18
6:23 am-2:02 pm
1 stop7h 39m
Cancun
Wed 5/27
8:00 am-4:12 pm
1 stop8h 12m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 5/29
12:51 pm-8:16 pm
1 stop7h 25m
Cancun
Thu 6/4
11:10 am-9:09 pm
1 stop9h 59m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 5/2
6:25 am-2:05 pm
1 stop7h 40m
Cancun
Sat 5/9
12:37 pm-11:59 pm
2 stops11h 22m
| 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 |
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, April is the cheapest month in which you can book a flight from Chicago to Cancún (average of $159). Flying from Chicago to Cancún in March is currently the most expensive (average of $228). 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 32% on the cost of your flight, compared to a flight at noon.
The most flights from CHI to CUN are scheduled on a Saturday (17 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 60% 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 $308.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 5h 50m.
Flights via Atlanta (ATL) offer the fastest connection on this route, with an average layover time of 1h 26m.
About 17% of weekly flights between Chicago and Cancún have experienced delays in the past year, with the average delay time being 151 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 15% of flights being delayed.
Entertainment
Boarding
Overall
Crew
Comfort
Food
Reviews
Anonymous,Mar 2026
KOA - HNL
Entertainment
Boarding
Overall
Crew
Comfort
Food
Reviews
Anonymous,Mar 2026
KOA - HNL
Entertainment
Boarding
Overall
Crew
Comfort
Food
Reviews
Anonymous,Mar 2026
KOA - HNL
Entertainment
Boarding
Overall
Crew
Comfort
Food
Reviews
Anonymous,Mar 2026
KOA - HNL
Entertainment
Boarding
Overall
Crew
Comfort
Food
Reviews
Anonymous,Mar 2026
KOA - HNL
Entertainment
Boarding
Overall
Crew
Comfort
Food
Reviews
Anonymous,Mar 2026
KOA - HNL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$320 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$139 | Average$341 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$140 | Average$351 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$158 | Average$1,978 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$188 | Average$426 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$250 | Average$465 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$262 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$279 | Average$387 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$283 | Average$517 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$291 | Average$520 | FlexibilityNo cancel fee | On-time63% |