
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $168 (Frontier) |
One-way from | $141 (Expedia) |
Popular in | September |
Cheapest in | January |
Average price | $311 |
Good round-trip deal | $243 or less |
Good one-way deal | $202 or less |
Fly from
Fly to
Route
Depart
Return
CancúnChicago
CUN - ORD
CUNORD
Cancun
Tue 4/14
12:55 pm-5:00 pm
Nonstop4h 05m
Chicago O'Hare Intl
Sun 4/19
5:48 am-12:33 pm
1 stop6h 45m
CancúnChicago
CUN - ORD
CUNORD
Cancun
Fri 5/8
3:43 pm-12:58 am
1 stop9h 15m
Chicago O'Hare Intl
Mon 5/11
11:00 pm-10:06 am
1 stop11h 06m
CancúnChicago
CUN - ORD
CUNORD
Cancun
Fri 4/17
3:24 pm-12:45 am
1 stop9h 21m
Chicago O'Hare Intl
Mon 4/20
10:45 pm-10:06 am
1 stop11h 21m
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Tue 5/12
8:00 am-9:09 pm
1 stop13h 09m
Chicago Midway
Tue 5/19
12:53 pm-8:16 pm
1 stop7h 23m
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Tue 4/21
12:40 pm-10:28 pm
1 stop9h 48m
Chicago Midway
Sun 4/26
6:00 am-2:01 pm
1 stop8h 01m
CancúnChicago
CUN - ORD
CUNORD
Cancun
Tue 4/21
1:50 pm-8:16 pm
1 stop6h 26m
Chicago O'Hare Intl
Sun 4/26
9:48 am-8:15 pm
1 stop10h 27m
CancúnChicago
CUN - ORD
CUNORD
Cancun
Thu 5/7
8:00 am-6:05 pm
2 stops10h 05m
Chicago O'Hare Intl
Tue 5/12
9:25 am-8:16 pm
2 stops10h 51m
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Thu 5/14
8:00 am-9:09 pm
1 stop13h 09m
Chicago Midway
Tue 5/19
6:23 am-12:40 pm
1 stop6h 17m
CancúnChicago
CUN - ORD
CUNORD
Cancun
Wed 5/13
12:11 pm-4:16 pm
Nonstop4h 05m
Chicago O'Hare Intl
Sat 5/16
10:31 am-2:26 pm
Nonstop3h 55m
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Wed 5/13
8:00 am-9:09 pm
1 stop13h 09m
Chicago Midway
Sat 5/16
10:45 am-8:16 pm
1 stop9h 31m
| 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 Accuracy2 stars | Trust Score*2 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 76 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, August is the cheapest month in which you can book a flight from Cancún to Chicago (average of $80). Flying from Cancún to Chicago in June is currently the most expensive (average of $243). 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 Monday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 on average).
About 15% 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 13% of flights being delayed.
Boarding
Crew
Entertainment
Overall
Food
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Crew
Entertainment
Overall
Food
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Crew
Entertainment
Overall
Food
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Crew
Entertainment
Overall
Food
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Crew
Entertainment
Overall
Food
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Crew
Entertainment
Overall
Food
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$277 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$209 | Average$325 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$271 | Average$310 | FlexibilityNo cancel fee | On-time71% |