Washington to Chicago in October 2026
Round trips departing in October · Economy · Prices per person in USD
Prices updated
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 | 2 $336 | 3 $351 | 4 | |||
| 5 | 6 | 7 | 8 | 9 $404 | 10 | 11 |
| 12 | 13 | 14 | 15 | 16 | 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 2 – 5 3 nights · leave Fri$336United Airlines 1 stop · 2h 14mBook
-
Oct 3 – 7 4 nights · leave Sat$351Frontier Airlines 1 stop · 2h 24mBook
-
Oct 2 – 4 2 nights · leave Fri$353United Airlines 1 stop · 2h 14mBook
-
Oct 2 – 7 5 nights · leave Fri$380Frontier Airlines 1 stop · 6h 14mBook
-
Oct 9 – 12 3 nights · leave Fri$404Frontier Airlines Nonstop · 2h 23mBook
Prices change often. The booking site shows the final price before you pay.
Cheapest by trip length
Good to know for October
October vs other months
Cheapest round trip per departure month| Month | Cheapest round trip |
|---|---|
| September 2026 | No fares found yet |
| October 2026 | $336 |
| November 2026 | $266 (cheapest month) |
| December 2026 | No fares found yet |
| January 2027 | No fares found yet |
| February 2027 | No fares found yet |
| March 2027 | No fares found yet |
| April 2027 | No fares found yet |
| May 2027 | No fares found yet |
| June 2027 | $403 |
| July 2027 | $428 |
Washington to Chicago in October: questions
What's the cheapest date to fly from Washington to Chicago in October 2026?
Leaving Friday, October 2 and returning Monday, October 5 (3 nights) for $336 round trip on United Airlines, the cheapest of the 5 date combinations we track that month.
How much is a round trip from Washington to Chicago in October 2026?
From $336. Half of the 5 date combinations we track are under $353. Prices are per person in USD and change often.
Is October a cheap month to fly from Washington to Chicago?
It ranks 2 of 4 months we have prices for. The cheapest month is November 2026, from $266.