Cheap flights from Chicago Midway Airport to Guadalajara from $123

The cheapest month to fly to Guadalajara from Chicago Midway Airport is in January. Flight prices, which tend to average around $321, are often lower during this time because this is during the off-season. If you’re not able to fly to Guadalajara in January, then March is your next best option. Flight prices from Chicago Midway Airport to Guadalajara during March average around $367.

Our data shows that Sunday is the least expensive day to fly to Guadalajara. Tickets to fly out on this day can be as low as $368. Flights from Chicago Midway Airport to Guadalajara on a Friday will generally be more expensive and average around $397. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Flying to Guadalajara from Chicago Midway Airport in the morning is the least expensive time of day to depart. momondo users have found prices as low as $378 when looking at flights departing in the morning. In contrast, the most expensive time of day to depart to Guadalajara is in the afternoon when prices are around $408.

Fly from Chicago Midway to Guadalajara Miguel Hidal for the best Chicago Midway - Guadalajara Miguel Hidal flight prices

You are more likely to see cheaper flights to Guadalajara from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Guadalajara for around $450 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Guadalajara from Chicago Midway Airport for as low as $325 on momondo.

There are 2 cabin classes available to choose from on Chicago Midway Airport to Guadalajara flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Historically, on average around 19% of flights between Chicago and Guadalajara have experienced a delay on any given week. The average delay length over the past 12 months has been 145 minutes.

Generally, flights departing in the evening tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, Volaris have had the least number of delays on this route over the last 12 months; with about 19% of their flights experiencing any sort of delay.

As of August 2026, there are 1 flights per day flying from Chicago Midway Airport to Guadalajara. The most common time of day flights depart is 8:00PM, with 100% of flights taking off in the evening.

As of August 2026, 8 flights take off from Chicago Midway Airport and land in Guadalajara each week. The most common flight departure day for this route is Mon, with 25% of weekly flights taking off on this day.