Spirit's Big Front Seats offer wider seats with 11 inches more legroom.
Spirit's Wi-Fi is available for browsing and streaming at a cost.
Round-trip from | $232 (Cheapflightsfares) |
---|---|
One-way from | $92 (Cheapflightsfares) |
Popular in | March |
Cheapest in | September |
Average price | $347 |
Good round-trip deal | $352 or less |
Good one-way deal | $124 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 11/16
10:40 am-3:25 pm
Nonstop3h 45m
Cancun
Thu 11/20
1:45 pm-4:30 pm
Nonstop3h 45m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 11/15
5:05 am-2:00 pm
1 stop7h 55m
Cancun
Thu 11/20
1:45 pm-4:30 pm
Nonstop3h 45m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 10/4
9:00 am-7:20 pm
1 stop10h 20m
Cancun
Tue 10/7
3:38 pm-7:36 pm
Nonstop3h 58m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 10/18
6:30 am-1:40 pm
1 stop7h 10m
Cancun
Sat 11/1
11:55 am-8:20 pm
2 stops8h 25m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 11/28
6:45 am-3:34 pm
1 stop7h 49m
Cancun
Tue 12/2
6:00 am-1:12 pm
1 stop8h 12m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 11/15
1:04 pm-9:20 pm
1 stop7h 16m
Cancun
Wed 11/19
12:25 pm-10:41 pm
1 stop11h 16m
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 11/28
6:45 am-9:20 pm
1 stop13h 35m
Cancun
Fri 12/5
6:00 am-1:12 pm
1 stop8h 12m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 12/9
12:55 pm-8:25 pm
1 stop6h 30m
Cancun
Sat 12/13
11:55 am-2:45 pm
Nonstop3h 50m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 11/17
8:40 am-1:25 pm
Nonstop3h 45m
Cancun
Fri 11/21
6:55 pm-12:10 am
1 stop6h 15m
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Tue 11/11
6:20 am-5:00 pm
2 stops9h 40m
Cancun
Sat 11/15
1:50 pm-7:05 pm
1 stop6h 15m
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, January is the cheapest month in which you can book a flight from Chicago to Cancún (average of $360). Flying from Chicago to Cancún in March is currently the most expensive (average of $492). 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 evening. By choosing this option you can save up to 44% on the cost of your flight, compared to a flight at noon.
Travelers seeking maximum savings on their Chicago to Cancún flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to CUN are scheduled on a Thursday (7 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (5 on average).
Atlanta (ATL) – chosen by Cheapflights users on 33% of 1-stop itineraries from Chicago to Cancún on Cheapflights.
Monterrey (MTY) is the most affordable 1-stop option, with an average round-trip price of $344.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 6h 11m.
Flights via Mexico City (MEX) offer the fastest connection on this route, with an average layover time of 1h 38m.
Entertainment
Food
Overall
Comfort
Crew
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Food
Overall
Comfort
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Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Food
Overall
Comfort
Crew
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Food
Overall
Comfort
Crew
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Food
Overall
Comfort
Crew
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Food
Overall
Comfort
Crew
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$132 | Average$332 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$161 | Average$484 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$168 | Average$537 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$172 | Average$457 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$180 | Average$618 | FlexibilityNo cancel fee | On-time79% | |
Cheapest$191 | Average$456 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$205 | Average$685 | FlexibilityNo cancel fee | On-time67% | |
Cheapest$251 | Average$322 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$266 | Average$608 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$338 | Average$542 | FlexibilityNo cancel fee | On-time71% |