Chicago to New York 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 $304 | 2 $273 | 3 | 4 $295 | |||
| 5 | 6 | 7 $375 | 8 $333 | 9 $320 | 10 | 11 |
| 12 $387 | 13 $312 | 14 | 15 | 16 | 17 $333 | 18 |
| 19 $273 | 20 $257 | 21 $230 | 22 $264 | 23 $284 | 24 $257 | 25 |
| 26 | 27 $240 | 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 21 – 27 6 nights · leave Wed$230Frontier Airlines 1 stop · 6h 25mBook
-
Oct 27 – 29 2 nights · leave Tue$240Frontier Airlines 1 stop · 4h 33mBook
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Oct 20 – 26 6 nights · leave Tue$257Southwest Airlines Nonstop · 2h 10mBook
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Oct 24 – 30 6 nights · leave Sat$257American Airlines Nonstop · 2h 25mBook
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Oct 22 – 28 6 nights · leave Thu$264Frontier Airlines 1 stop · 5h 51mBook
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Oct 2 – 4 2 nights · leave Fri$273Frontier Airlines 1 stop · 5h 39mBook
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Oct 19 – 22 3 nights · leave Mon$273United Airlines Nonstop · 2h 22mBook
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Oct 23 – 29 6 nights · leave Fri$284Frontier Airlines 1 stop · 4h 29mBook
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Oct 4 – 6 2 nights · leave Sun$295Southwest Airlines 1 stop · 2h 05mBook
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Oct 2 – 5 3 nights · leave Fri$297Frontier Airlines 1 stop · 5h 39mBook
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 | $249 |
| October 2026 | $230 |
| November 2026 | $271 |
| December 2026 | $147 (cheapest month) |
| January 2027 | $152 |
| February 2027 | No fares found yet |
| March 2027 | $279 |
| April 2027 | $327 |
| May 2027 | No fares found yet |
| June 2027 | $328 |
| July 2027 | $334 |
Chicago to New York in October: questions
What's the cheapest date to fly from Chicago to New York in October 2026?
Leaving Wednesday, October 21 and returning Tuesday, October 27 (6 nights) for $230 round trip on Frontier Airlines, the cheapest of the 21 date combinations we track that month.
How much is a round trip from Chicago to New York in October 2026?
From $230. Half of the 21 date combinations we track are under $304. Prices are per person in USD and change often.
Is October a cheap month to fly from Chicago to New York?
It ranks 3 of 9 months we have prices for. The cheapest month is December 2026, from $147.