Cheap flights from Dallas to Chicago from $50

The month of October is, on average, the cheapest month to fly to Chicago from Dallas, with most prices found around $170. If you’re not able to fly to Chicago in October, then January is your next best option. Flight prices from Dallas to Chicago during January average around $172.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $248. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Dallas to Chicago for around $776.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Dallas to Chicago during this time can be as low as $225. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $620.

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

You are more likely to see cheaper flights to Chicago from Dallas when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $234 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Dallas for as low as $175 on momondo.

There are 4 cabin classes available to choose from on Dallas to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Southwest, United Airlines, and Delta are the most popular carriers operating from Dallas to Chicago

Frontier, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Dallas according to our data. Frontier is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 18% 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 151 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening 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. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 13% of their flights experiencing any sort of delay.

As of April 2026, there are 73 flights per day flying from Dallas to Chicago. The most common time of day flights depart is 12:00PM, with 45% of flights taking off in the afternoon.

The number of flights available between Dallas and Chicago is 514 per week as of April 2026. The most frequent departure day is Fri, with 17% of weekly flights leaving on this day.