
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $241 (Justfly.com) |
One-way from | $115 (Frontier) |
Popular in | December |
Cheapest in | September |
Average price | $470 |
Good round-trip deal | $337 or less |
Good one-way deal | $121 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Wed 5/13
8:10 am-8:16 pm
1 stop12h 06m
Cancun
Wed 5/20
12:45 pm-8:26 pm
1 stop7h 41m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Wed 6/17
11:30 am-8:25 pm
2 stops8h 55m
Cancun
Wed 6/24
12:39 pm-12:07 am
1 stop11h 28m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 7/23
11:05 am-8:15 pm
1 stop9h 10m
Cancun
Tue 7/28
8:00 am-10:15 pm
1 stop14h 15m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 7/21
6:35 am-6:29 pm
2 stops11h 54m
Cancun
Tue 7/28
1:30 pm-10:39 pm
1 stop9h 09m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Wed 5/27
2:59 pm-8:16 pm
1 stop5h 17m
Cancun
Wed 6/3
12:39 pm-12:08 am
2 stops11h 29m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 6/16
9:17 am-8:25 pm
2 stops11h 08m
Cancun
Tue 6/23
8:00 am-4:16 pm
1 stop8h 16m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 6/5
7:00 am-8:16 pm
2 stops13h 16m
Cancun
Mon 6/8
8:00 am-6:42 pm
1 stop10h 42m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 7/7
11:30 am-8:15 pm
2 stops8h 45m
Cancun
Tue 7/14
8:00 am-4:44 pm
1 stop8h 44m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Thu 7/23
11:30 am-8:15 pm
2 stops8h 45m
Cancun
Tue 7/28
8:00 am-6:29 pm
2 stops10h 29m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 5/30
9:25 am-8:16 pm
2 stops10h 51m
Cancun
Mon 6/8
12:39 pm-11:59 pm
2 stops11h 20m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
Booking 65 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 $345). Flying from Chicago to Cancún in March is currently the most expensive (average of $586). 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 30% on the cost of your flight, compared to a flight at noon.
The most flights from CHI to CUN are scheduled on a Saturday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (11 on average).
Mexico City (MEX) – 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 $355.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 6h 36m.
Flights via Mexico City (MEX) offer the fastest connection on this route, with an average layover time of 1h 39m.
About 20% of weekly flights between Chicago and Cancún have experienced delays in the past year, with the average delay time being 157 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 16% of flights being delayed.
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$314 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$147 | Average$348 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$156 | Average$390 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$158 | Average$2,017 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$189 | Average$431 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$193 | Average$516 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$480 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$289 | Average$508 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$291 | Average$495 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$319 | Average$510 | FlexibilityNo cancel fee | On-time71% |