
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $218 (Kiwi.com) |
One-way from | $86 (Mytrip) |
Popular in | December |
Cheapest in | January |
Average price | $349 |
Good round-trip deal | $251 or less |
Good one-way deal | $102 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
ChicagoMexico City
ORD - TLC
ORDTLC
Chicago O'Hare Intl
Wed 5/13
2:15 am-8:25 am
1 stop7h 10m
Mexico City Toluca Intl
Mon 5/18
6:00 am-12:45 am
1 stop17h 45m
ChicagoGuadalajara
ORD - GDL
ORDGDL
Chicago O'Hare Intl
Mon 5/4
1:40 am-11:18 am
1 stop10h 38m
Guadalajara Miguel Hidal
Sun 5/31
7:01 am-12:09 pm
Nonstop4h 08m
ChicagoMexico City
ORD - TLC
ORDTLC
Chicago O'Hare Intl
Thu 4/23
2:15 am-8:25 am
1 stop7h 10m
Mexico City Toluca Intl
Mon 4/27
6:00 am-12:45 am
1 stop17h 45m
ChicagoGuadalajara
ORD - GDL
ORDGDL
Chicago O'Hare Intl
Sat 4/18
8:25 pm-11:50 pm
Nonstop4h 25m
Guadalajara Miguel Hidal
Wed 4/22
6:50 pm-11:45 pm
Nonstop3h 55m
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
ChicagoMexico City
ORD - MEX
ORDMEX
Chicago O'Hare Intl
Sun 4/12
1:20 am-4:45 am
Nonstop4h 25m
Mexico City Benito Juarez
Fri 4/17
5:45 am-10:50 am
Nonstop4h 05m
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
Currently, May is the cheapest month in which you can book a flight from Chicago to Mexico (average of $48). Flying from Chicago to Mexico in December is currently the most expensive (average of $183). 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.
A simple way to save on the total cost of your ticket is to fly from Chicago to Mexico in the evening. If you’re flexible enough to do this you can expect to save up to 18% on your trip compared to booking a flight in the morning.
Travelers seeking maximum savings on their Chicago to Mexico flight should consider departing on Tuesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to MX0 are scheduled on a Monday (15 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 on average).
About 18% of weekly flights between Chicago and Mexico 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 at night tend to experience delays more often.
Thursday 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, Aeromexico have had the lowest number of delays on this route, with just 7% of flights being delayed.
Comfort
Food
Crew
Boarding
Overall
Entertainment
Reviews
Dane,Jan 2026
TYS - IAD
Comfort
Food
Crew
Boarding
Overall
Entertainment
Reviews
Dane,Jan 2026
TYS - IAD
Comfort
Food
Crew
Boarding
Overall
Entertainment
Reviews
Dane,Jan 2026
TYS - IAD
Comfort
Food
Crew
Boarding
Overall
Entertainment
Reviews
Dane,Jan 2026
TYS - IAD
Comfort
Food
Crew
Boarding
Overall
Entertainment
Reviews
Dane,Jan 2026
TYS - IAD
Comfort
Food
Crew
Boarding
Overall
Entertainment
Reviews
Dane,Jan 2026
TYS - IAD
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$48 | Average$354 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$129 | Average$249 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$139 | Average$341 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$140 | Average$424 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$154 | Average$450 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$158 | Average$860 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$165 | Average$364 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$196 | Average$567 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$250 | Average$465 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$259 | Average$553 | FlexibilityNo cancel fee | On-time71% |