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Cheap flights from New York to Chicago

Recently found return fares from $86, with November the cheapest month we know of. Compare dates, then book with the partner you choose.

Cheapest months to fly

Lowest recently found return fare in each month. Tap a month to see that month's calendar.

Typical return fare: $129 – $176 Middle half of the lowest fares we saw each day in the last 90 days (11 days of data). Anything below the range is a good price.

Good price
$130 Oct2026 $86 Nov2026 $114 Dec2026 $128 Jan2027 $131 Feb2027 $149 Mar2027 $161 Apr2027 $174 May2027 $177 Jul2027

New York → Chicago

November 2026

Mon Tue Wed Thu Fri Sat Sun 1 $182 2 3 4 $133 5 $161 6 $140 7 $159 8 9 10 11 $126 12 13 $129 14 $125 15 $161 16 17 $108 18 $86 19 $131 20 $135 21 22 23 $102 24 25 26 $173 27 $187 28 $252 29 $326 30
LowerHigherLowest this month

Lowest fares for the best day

  • Frontier AirlinesTue 10 Nov – Tue 17 Nov · 1 stop · 4h 56m $221
  • United AirlinesSat 7 Nov – Mon 9 Nov · Direct · 2h 45m $245
  • Frontier AirlinesFri 20 Nov – Thu 26 Nov · 1 stop · 4h 34m $255
  • Frontier AirlinesSat 7 Nov – Thu 12 Nov · 1 stop · 4h 56m $262
  • Frontier AirlinesTue 3 Nov – Thu 5 Nov · 1 stop · 5h 14m $273
See all flights for these dates

Airports in Chicago

  • ORDO'Hare
  • MDWMidway

Airports in New York

  • JFKJohn F. Kennedy
  • EWRNewark Liberty
  • LGALaGuardia

Watch this route

NYC
CHI

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More trips from New York

All flights from New York Chicago to New York flights
Atlantafrom $130 Miamifrom $139 TPAfrom $144 FLLfrom $147 Orlandofrom $165 Torontofrom $189 Houstonfrom $204 Dallasfrom $208

FAQ

Questions about this route

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Help center Contact us
01What is the cheapest month to fly from New York to Chicago?

Based on recently found fares, November 2026 has the lowest price we know of, from $86. Prices change often, so check the calendar for current fares.

02Which airports serve Chicago?

Chicago is served by O'Hare (ORD), Midway (MDW). Searching the city code compares all of them at once.

03Are the prices on this page final?

No. They are recently found fares. When you open a deal, the partner shows the live price, including taxes and fees, before you pay.

04How can I get an alert when flights to Chicago get cheaper?

Use the price alert on this page. Choose your dates or a whole month and we will email you when the fare drops.