New York 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 $249 | 2 $324 | 3 $257 | 4 $271 | |||
| 5 $295 | 6 $295 | 7 $250 | 8 | 9 $414 | 10 $257 | 11 |
| 12 $288 | 13 | 14 $243 | 15 | 16 | 17 $248 | 18 |
| 19 $286 | 20 | 21 $253 | 22 | 23 | 24 | 25 |
| 26 | 27 | 28 $231 | 29 $275 | 30 $258 | 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 28 – 31 3 nights · leave Wed$231Frontier Airlines 1 stop · 5h 00mBook
-
Oct 14 – 21 7 nights · leave Wed$243Frontier Airlines 1 stop · 5h 08mBook
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Oct 17 – 23 6 nights · leave Sat$248United Airlines Nonstop · 2h 43mBook
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Oct 1 – 3 2 nights · leave Thu$249Frontier Airlines 1 stop · 6h 00mBook
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Oct 7 – 14 7 nights · leave Wed$250Frontier Airlines 1 stop · 5h 03mBook
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Oct 21 – 25 4 nights · leave Wed$253Frontier Airlines 1 stop · 5h 06mBook
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Oct 3 – 6 3 nights · leave Sat$257Frontier Airlines 1 stop · 5h 03mBook
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Oct 10 – 13 3 nights · leave Sat$257Frontier Airlines 1 stop · 5h 09mBook
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Oct 30 – Nov 2 3 nights · leave Fri$258Frontier Airlines 1 stop · 4h 56mBook
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Oct 14 – 18 4 nights · leave Wed$262Frontier Airlines 1 stop · 5h 06mBook
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 | $253 |
| October 2026 | $231 (cheapest month) |
| November 2026 | $243 |
| December 2026 | $295 |
| January 2027 | $284 |
| February 2027 | No fares found yet |
| March 2027 | $293 |
| April 2027 | $287 |
New York to Chicago in October: questions
What's the cheapest date to fly from New York to Chicago in October 2026?
Leaving Wednesday, October 28 and returning Saturday, October 31 (3 nights) for $231 round trip on Frontier Airlines, the cheapest of the 29 date combinations we track that month.
How much is a round trip from New York to Chicago in October 2026?
From $231. Half of the 29 date combinations we track are under $275. Prices are per person in USD and change often.
Is October a cheap month to fly from New York to Chicago?
Yes. It's the cheapest of the 7 months ahead we have prices for.