Chicago to New York in December 2026
Round trips departing in December · 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 December fares drop below your price.December 2026 by departure day
Cheapest round trip leaving that day| Mon | Tue | Wed | Thu | Fri | Sat | Sun |
|---|---|---|---|---|---|---|
| 1 $277 | 2 | 3 | 4 | 5 | 6 | |
| 7 | 8 | 9 | 10 | 11 $147 | 12 | 13 $286 |
| 14 $284 | 15 | 16 $290 | 17 | 18 | 19 | 20 |
| 21 | 22 | 23 | 24 $318 | 25 | 26 | 27 |
| 28 | 29 | 30 $269 | 31 |
Empty days: no round trip found for that departure date yet. Green = cheapest third of the month.
Cheapest dates in December 2026
Round trip, per person-
Dec 11 – 16 5 nights · leave Fri$147United Airlines Nonstop · 2h 11mBook
-
Dec 11 – 13 2 nights · leave Fri$267Frontier Airlines 1 stop · 5h 36mBook
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Dec 30 – Jan 5, 2027 6 nights · leave Wed$269United Airlines Nonstop · 2h 20mBook
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Dec 1 – 4 3 nights · leave Tue$277Frontier Airlines 1 stop · 5h 34mBook
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Dec 14 – 18 4 nights · leave Mon$284Frontier Airlines 1 stop · 4h 31mBook
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Dec 13 – 18 5 nights · leave Sun$286Southwest Airlines Nonstop · 2h 05mBook
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Dec 16 – 24 8 nights · leave Wed$290American Airlines Nonstop · 2h 18mBook
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Dec 24 – 27 3 nights · leave Thu$318Southwest Airlines Nonstop · 2h 05mBook
Prices change often. The booking site shows the final price before you pay.
Cheapest by trip length
Good to know for December
December 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 December: questions
What's the cheapest date to fly from Chicago to New York in December 2026?
Leaving Friday, December 11 and returning Wednesday, December 16 (5 nights) for $147 round trip on United Airlines, the cheapest of the 8 date combinations we track that month.
How much is a round trip from Chicago to New York in December 2026?
From $147. Half of the 8 date combinations we track are under $281. Prices are per person in USD and change often.
Is December a cheap month to fly from Chicago to New York?
Yes. It's the cheapest of the 9 months ahead we have prices for.