
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $254 (Frontier) |
One-way from | $117 (FlightHub) |
Popular in | December |
Cheapest in | September |
Average price | $436 |
Good round-trip deal | $358 or less |
Good one-way deal | $124 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 7/30
11:05 am-8:15 pm
1 stop9h 10m
Cancun
Thu 8/6
2:10 pm-10:36 pm
1 stop8h 26m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Wed 7/15
8:52 am-8:15 pm
2 stops11h 23m
Cancun
Tue 7/21
8:00 am-8:31 pm
2 stops12h 31m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 5/30
7:00 am-8:16 pm
2 stops13h 16m
Cancun
Sat 6/6
12:50 pm-9:56 pm
1 stop9h 06m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 8/7
1:48 pm-8:15 pm
1 stop6h 27m
Cancun
Wed 8/12
2:10 pm-7:56 am
2 stops17h 46m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 8/21
10:44 am-2:26 pm
Nonstop3h 42m
Cancun
Tue 8/25
12:11 pm-4:04 pm
Nonstop3h 53m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 6/6
7:52 am-11:45 am
Nonstop3h 53m
Cancun
Wed 6/10
12:11 pm-4:16 pm
Nonstop4h 05m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 7/10
9:55 am-1:30 pm
Nonstop3h 35m
Cancun
Tue 7/14
12:40 pm-7:05 pm
1 stop6h 25m
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
Wed 6/17
9:48 am-8:25 pm
1 stop10h 37m
Cancun
Wed 6/24
12:39 pm-11:59 pm
2 stops11h 20m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 7/6
9:17 am-8:25 pm
2 stops11h 08m
Cancun
Fri 7/10
8:00 am-10:15 pm
1 stop14h 15m
| 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 (9 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 21% 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 in the morning 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
Overall
Boarding
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Overall
Boarding
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Overall
Boarding
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Overall
Boarding
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Overall
Boarding
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Overall
Boarding
Food
Comfort
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$312 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$145 | Average$351 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$155 | Average$2,020 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$189 | Average$430 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$190 | Average$390 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$480 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$289 | Average$510 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$293 | Average$497 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$317 | Average$515 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$319 | Average$511 | FlexibilityNo cancel fee | On-time71% |