August is the cheapest month to fly this route, with average fares around $159 round trip.
Average round-trip fares by departure month, based on current availability.
| Month | Avg Price | Lowest | Relative Cost | |
|---|---|---|---|---|
| May 2026 | $223 | $169 | Peak | |
| June 2026 | $182 | $128 | ||
| July 2026 | $169 | $148 | ||
| August 2026 | $159 | $150 | Best |
Departing on Tuesday offers the lowest average fares at $166. Friday departures are the most expensive at $198, a difference of $32.
The best time to fly is August. Set up an alert and we'll notify you when prices drop.
Get Started Free →The cheapest month to fly from Dallas to Chicago is August, with average round-trip fares around $159. The lowest fare found in August is $150.
Tuesday departures are the cheapest, averaging $166 round trip. The most expensive day is Friday at $198.
Based on current pricing trends, booking for August travel offers the best value. Avoid May if possible, as fares average $223 compared to $159 in the cheapest month. June is a solid middle-ground option at $182.
Flying in August instead of May can save you approximately $64 per round trip. The cheapest month averages $159 while the most expensive averages $223.
Airlines, flight times, price calendar, and more for Dallas to Chicago
View DFW → ORD Details