
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $249 (FlightHub) |
One-way from | $98 (FlightHub) |
Popular in | December |
Cheapest in | September |
Average price | $526 |
Good round-trip deal | $366 or less |
Good one-way deal | $130 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Wed 5/6
10:30 am-2:00 pm
Nonstop3h 30m
Cancun
Fri 5/15
4:10 pm-7:50 pm
Nonstop3h 40m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 4/24
6:00 am-2:01 pm
1 stop8h 01m
Cancun
Sat 5/9
12:45 pm-9:09 pm
1 stop8h 24m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sun 5/3
6:25 am-6:35 pm
2 stops12h 10m
Cancun
Wed 5/6
6:00 am-4:42 pm
2 stops10h 42m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 5/17
6:23 am-2:02 pm
1 stop7h 39m
Cancun
Wed 5/20
8:00 am-6:33 pm
2 stops10h 33m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sun 7/5
7:10 am-12:47 pm
1 stop5h 37m
Cancun
Wed 7/8
9:55 am-8:24 pm
2 stops10h 29m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 4/17
5:53 pm-12:00 pm
2 stops18h 07m
Cancun
Tue 4/21
3:15 pm-8:01 am
2 stops16h 46m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 5/8
9:35 am-1:10 pm
Nonstop3h 35m
Cancun
Mon 5/11
4:10 pm-7:50 pm
Nonstop3h 40m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 3/21
7:10 am-3:04 pm
1 stop7h 54m
Cancun
Mon 3/23
12:44 pm-9:10 pm
1 stop8h 26m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 4/28
5:15 am-12:40 pm
1 stop7h 25m
Cancun
Wed 5/6
2:00 pm-9:38 pm
1 stop7h 38m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sun 4/26
5:15 am-6:35 pm
2 stops13h 20m
Cancun
Sat 5/2
11:10 am-11:59 pm
2 stops12h 49m
| 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 $167). Flying from Chicago to Cancún in March is currently the most expensive (average of $226). 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 Monday (15 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 16% of weekly flights between Chicago and Cancún have experienced delays in the past year, with the average delay time being 150 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 13% of flights being delayed.
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Anonymous,Mar 2026
KOA - HNL
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Anonymous,Mar 2026
KOA - HNL
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Anonymous,Mar 2026
KOA - HNL
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Anonymous,Mar 2026
KOA - HNL
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
Anonymous,Mar 2026
KOA - HNL
Boarding
Comfort
Crew
Food
Overall
Entertainment
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% |