Cheap flights from Dallas/Fort Worth Airport to Chicago from $102

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Dallas/Fort Worth Airport, with most prices found around $166. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Dallas/Fort Worth Airport during the month January is also very affordable. Most momondo users find prices during this month for around $179.

According to our data, Sunday is the cheapest day to fly to Chicago Midway Airport from Dallas/Fort Worth Airport. The lowest ticket price found for a Sunday departure recently was $164. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Friday is the most expensive day to depart from Dallas/Fort Worth Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $191.

Flying to Chicago Midway Airport from Dallas/Fort Worth Airport at noon is the least expensive time of day to depart. momondo users have found prices as low as $210 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $252. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Dallas/Fort Worth to Chicago Midway for the best Dallas/Fort Worth - Chicago Midway flight prices

You are more likely to see cheaper flights to Chicago Midway Airport from Dallas/Fort Worth Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $231 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Dallas/Fort Worth Airport for as low as $136 on momondo.

There is only 1 cabin class available to choose from on Dallas/Fort Worth Airport to Chicago Midway Airport 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 22% of flights between Dallas and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 152 minutes.

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

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

According to our data, Frontier have had the least number of delays on this route over the last 12 months; with about 23% of their flights experiencing any sort of delay.

As of July 2026, there are 1 flights per day flying from Dallas/Fort Worth Airport to Chicago Midway Airport. The most common time of day flights depart is 3:00PM, with 100% of flights taking off in the afternoon.

7 flights are operational weekly from Dallas/Fort Worth Airport to Chicago Midway Airport as of July 2026. The most popular departure day for this route is Mon, with 29% of flights per week taking off on this day.