Dallas to Chicago in October 2026
Round trips departing in October · Economy · Prices per person in USD
Prices updated
Typical in October
$308
Median of 6 date combinations
Usual on this route
$249
October's cheapest is 1% less
Buy now or wait? We're still learning this route. We have 1 day of prices so far and need about a week to say whether to book or wait.
Not ready to book? Get an email when October fares drop below your price.October 2026 by departure day
Cheapest round trip leaving that day| Mon | Tue | Wed | Thu | Fri | Sat | Sun |
|---|---|---|---|---|---|---|
| 1 $341 | 2 $317 | 3 | 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 $342 | 11 |
| 12 | 13 | 14 $275 | 15 $298 | 16 $246 | 17 | 18 |
| 19 | 20 | 21 | 22 | 23 | 24 | 25 |
| 26 | 27 | 28 | 29 | 30 | 31 |
Empty days: no round trip found for that departure date yet. Green = cheapest third of the month.
Cheapest dates in October 2026
Round trip, per person-
Oct 16 – 19 3 nights · leave Fri$246Contour Airlines 1 stop · 3h 40mBook
-
Oct 14 – 18 4 nights · leave Wed$275Frontier Airlines Nonstop · 2h 42mBook
-
Oct 15 – 18 3 nights · leave Thu$298Contour Airlines 1 stop · 3h 40mBook
-
Oct 2 – 4 2 nights · leave Fri$317Southwest Airlines Nonstop · 2h 15mBook
-
Oct 1 – 4 3 nights · leave Thu$341Frontier Airlines Nonstop · 2h 23mBook
-
Oct 10 – 12 2 nights · leave Sat$342Frontier Airlines Nonstop · 2h 23mBook
Prices change often. The booking site shows the final price before you pay.
Good to know for October
Airlines with cheap fares
3 airlines
Most often: Frontier Airlines, Contour Airlines, Southwest Airlines.
October vs other months
Cheapest round trip per departure month| Month | Cheapest round trip |
|---|---|
| September 2026 | No fares found yet |
| October 2026 | $246 |
| November 2026 | $145 (cheapest month) |
| December 2026 | $211 |
Dallas to Chicago in October: questions
What's the cheapest date to fly from Dallas to Chicago in October 2026?
Leaving Friday, October 16 and returning Monday, October 19 (3 nights) for $246 round trip on Contour Airlines, the cheapest of the 6 date combinations we track that month.
How much is a round trip from Dallas to Chicago in October 2026?
From $246. Half of the 6 date combinations we track are under $308. Prices are per person in USD and change often.