
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $147 (Frontier) |
One-way from | $133 (Super.com) |
Popular in | September |
Cheapest in | April |
Average price | $224 |
Good round-trip deal | $216 or less |
Good one-way deal | $164 or less |
Fly from
Fly to
Route
Depart
Return
CancúnChicago
CUN - ORD
CUNORD
Cancun
Wed 7/22
12:11 pm-4:16 pm
Nonstop4h 05m
Chicago O'Hare Intl
Sun 7/26
5:00 am-12:58 pm
1 stop7h 58m
CancúnChicago
CUN - ORD
CUNORD
Cancun
Thu 5/28
3:38 pm-7:45 pm
Nonstop4h 07m
Chicago O'Hare Intl
Sun 5/31
9:17 am-1:10 pm
Nonstop3h 53m
CancúnChicago
CUN - ORD
CUNORD
Cancun
Thu 6/4
4:31 pm-12:07 am
1 stop7h 36m
Chicago O'Hare Intl
Tue 6/30
5:30 am-2:39 pm
1 stop9h 09m
CancúnChicago
CUN - ORD
CUNORD
Cancun
Tue 6/30
11:15 am-12:08 am
1 stop12h 53m
Chicago O'Hare Intl
Sun 7/5
6:30 am-1:00 pm
1 stop6h 30m
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Thu 7/16
8:00 am-10:15 pm
1 stop14h 15m
Chicago Midway
Mon 7/20
6:00 am-11:20 am
1 stop5h 20m
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Thu 5/14
11:10 am-9:09 pm
1 stop9h 59m
Chicago Midway
Mon 5/18
10:59 am-8:16 pm
1 stop9h 17m
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Wed 6/10
8:00 am-4:16 pm
1 stop8h 16m
Chicago Midway
Wed 6/17
11:05 am-8:25 pm
1 stop9h 20m
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Thu 5/28
8:00 am-9:09 pm
1 stop13h 09m
Chicago Midway
Sun 5/31
10:59 am-8:16 pm
1 stop9h 17m
CancúnChicago
CUN - ORD
CUNORD
Cancun
Wed 7/22
8:00 am-8:31 pm
2 stops12h 31m
Chicago O'Hare Intl
Sun 7/26
6:30 am-1:00 pm
1 stop6h 30m
CancúnChicago
CUN - ORD
CUNORD
Cancun
Wed 6/10
8:00 am-5:04 pm
1 stop9h 04m
Chicago O'Hare Intl
Wed 6/17
7:01 am-8:25 pm
2 stops13h 24m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
The price you pay for your flight from Cancún to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 48 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, June is the cheapest month in which you can book a flight from Cancún to Chicago (average of $52). Flying from Cancún to Chicago in September is currently the most expensive (average of $167). 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 Cancún to Chicago in the evening. By choosing this option you can save up to 64% on the cost of your flight, compared to a flight at noon.
The most flights from CUN to CHI are scheduled on a Thursday (13 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (6 on average).
About 16% of weekly flights between Cancún and Chicago have experienced delays in the past year, with the average delay time being 155 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Wednesday 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, Southwest have had the lowest number of delays on this route, with just 15% of flights being delayed.
Overall
Crew
Entertainment
Food
Boarding
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Crew
Entertainment
Food
Boarding
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Crew
Entertainment
Food
Boarding
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Crew
Entertainment
Food
Boarding
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Crew
Entertainment
Food
Boarding
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Crew
Entertainment
Food
Boarding
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$142 | Average$184 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$147 | Average$231 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$209 | Average$325 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$271 | Average$310 | FlexibilityNo cancel fee | On-time71% |