Cheap flights from Dallas to Chicago from $105

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Dallas, with most prices found around $175. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Dallas during the month January is also very affordable. Most momondo users find prices during this month for around $183.

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Dallas. The lowest ticket price found for a Tuesday departure recently was $176. 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, Saturday is the most expensive day to depart from Dallas because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $219.

Flying to Chicago Midway Airport from Dallas in the evening is the least expensive time of day to depart. momondo users have found prices as low as $225 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $285. 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 - Chicago Midway flight prices

You are more likely to see cheaper flights to Chicago Midway Airport from Dallas when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $241 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 for as low as $148 on momondo.

There is only 1 cabin class available to choose from on Dallas 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 153 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.

Thursday 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 22% of their flights experiencing any sort of delay.

The number of flights available between Dallas and Chicago Midway Airport is 7 per day as of August 2026. The most frequent departure time is 3:00PM, with 52% of daily flights leaving in the afternoon.

As of August 2026, there are 52 flights per week flying from Dallas to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 23% of flights taking off on this day.