Cheap flights from Chicago to Dallas from $68

If you are unable to visit Dallas during the month of October, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $186.

On average, the least expensive day to fly to Dallas from Chicago is on a Friday. momondo users have found tickets for Friday departures for as low as $244. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Monday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $483.

Flying to Dallas from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $271 when looking at flights departing in the afternoon. At noon is when there is more demand to fly to Dallas, so prices are often more expensive at around $350 per ticket.

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

You are more likely to see cheaper flights to Dallas from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Dallas for around $256 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Dallas from Chicago for as low as $181 on momondo.

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

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

Frontier, United Airlines and American Airlines are the top three most popular airlines that fly to Dallas from Chicago according to our data. Frontier is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Dallas. Keep in mind that there are 7 different airlines that fly to Dallas on a routine basis, so you have a few additional options to choose from.

Historically, on average around 22% of flights between Chicago and Dallas have experienced a delay on any given week. The average delay length over the past 12 months has been 158 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.

Tuesday 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 18% of their flights experiencing any sort of delay.

As of May 2026, 85 flights take off from Chicago and land in Dallas each day. The most common flight departure time for this route is 3:00PM, with 36% of daily flights taking off in the afternoon.

The number of flights available between Chicago and Dallas is 596 per week as of May 2026. The most frequent departure day is Mon, with 16% of weekly flights leaving on this day.