
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $246 (Expedia) |
One-way from | $156 (Southwest) |
Popular in | December |
Cheapest in | February |
Average price | $262 |
Good round-trip deal | $178 or less |
Good one-way deal | $147 or less |
Fly from
Fly to
Route
Depart
Return
Price
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Thu 4/16
8:00 am-4:29 pm
1 stop8h 29m
Chicago Midway
Tue 4/21
9:27 am-8:15 pm
2 stops10h 48m
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Thu 4/23
3:15 pm-10:28 pm
1 stop7h 13m
Chicago Midway
Mon 4/27
6:00 am-2:01 pm
1 stop8h 01m
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Wed 7/22
8:00 am-9:45 pm
1 stop13h 45m
Chicago Midway
Sat 8/1
4:30 pm-8:55 am
1 stop16h 25m
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Thu 3/5
8:00 am-5:45 pm
1 stop10h 45m
Chicago Midway
Tue 3/10
6:00 am-11:34 am
1 stop5h 34m
CancúnChicago
CUN - MDW
CUNMDW
Cancun
Wed 4/29
10:00 am-4:26 pm
1 stop6h 26m
Chicago Midway
Thu 5/7
6:30 am-8:03 pm
1 stop13h 33m
Santiago de QuerétaroChicago
QRO - MDW
QROMDW
Santiago de Querétaro
Tue 4/7
8:25 am-5:22 pm
1 stop7h 57m
Chicago Midway
Tue 4/14
6:00 am-5:00 pm
2 stops12h 00m
Santiago de QuerétaroChicago
QRO - MDW
QROMDW
Santiago de Querétaro
Wed 4/8
8:25 am-5:22 pm
1 stop7h 57m
Chicago Midway
Wed 4/15
10:41 am-11:40 pm
2 stops13h 59m
MoreliaChicago
MLM - MDW
MLMMDW
Morelia
Fri 5/1
8:15 am-1:15 pm
Nonstop4h 00m
Chicago Midway
Sat 5/9
2:32 pm-5:32 pm
Nonstop4h 00m
Santiago de QuerétaroChicago
QRO - MDW
QROMDW
Santiago de Querétaro
Fri 5/1
6:00 am-4:26 pm
2 stops9h 26m
Chicago Midway
Mon 5/4
10:41 am-5:25 pm
1 stop7h 44m
GuadalajaraChicago
GDL - MDW
GDLMDW
Guadalajara Miguel Hidal
Sat 3/7
1:39 pm-5:34 pm
Nonstop3h 55m
Chicago Midway
Sat 3/21
7:54 pm-11:24 pm
Nonstop4h 30m
Currently, March is the cheapest month in which you can book a flight from Mexico to Chicago Midway Airport (average of $197). Flying from Mexico to Chicago Midway Airport in June is currently the most expensive (average of $325). 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.
One of the essential ways to save on airfare from Mexico to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 31% on airfare.
Travelers seeking maximum savings on their Mexico to Chicago Midway Airport flight should consider departing on Saturday evenings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
About 10% of weekly flights between Mexico and Chicago have experienced delays in the past year, with the average delay time being 125 minutes.
Historically, flights departing at night 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 Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Volaris have had the lowest number of delays on this route, with just 10% of flights being delayed.
Entertainment
Comfort
Overall
Food
Boarding
Crew
Reviews
Anonymous,Feb 2026
OAX - LAX
Entertainment
Comfort
Overall
Food
Boarding
Crew
Reviews
Anonymous,Feb 2026
OAX - LAX
Entertainment
Comfort
Overall
Food
Boarding
Crew
Reviews
Anonymous,Feb 2026
OAX - LAX
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$279 | Average$457 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$336 | Average$421 | FlexibilityNo cancel fee | On-time62% |