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Cheap flights from New York to Chicago

One-way from $103, found by travellers in the last 7 days. Aviasales checks the live price.

Departure
Return
Prices for nearby dates
Sun, Nov 15$145Mon, Nov 16$144Tue, Nov 17Any priceWed, Nov 18$103Thu, Nov 19Any priceFri, Nov 20$139Sat, Nov 21Any priceSun, Nov 22Any price

Cheapest one-way tickets

Recent finds on different dates, for 1 adult. Baggage and fare rules are shown on Aviasales, where the price is checked live.

Cheapest
$103
Frontier Airlines, flight F9 3287Found 3 days ago, 1 adult
Check price on Aviasales
6:30amNew YorkWed, Nov 18
Travel time 5h 14m, 1 stopLGAORD
10:44amChicagoWed, Nov 18
$118
Frontier Airlines, flight F9 3287Found 7 days ago, 1 adult
Check price on Aviasales
6:30amNew YorkTue, Oct 27
Travel time 5h, 1 stopLGAORD
10:30amChicagoTue, Oct 27
$118
Frontier Airlines, flight F9 3287Found 7 days ago, 1 adult
Check price on Aviasales
6:30amNew YorkWed, Oct 28
Travel time 5h, 1 stopLGAORD
10:30amChicagoWed, Oct 28
$118
Frontier Airlines, flight F9 3287Found 5 days ago, 1 adult
Check price on Aviasales
6:30amNew YorkWed, Nov 11
Travel time 5h, 1 stopLGAORD
10:30amChicagoWed, Nov 11
$125
Frontier Airlines, flight F9 3453Found 7 days ago, 1 adult
Check price on Aviasales
5:30pmNew YorkThu, Nov 12
Travel time 4h 56m, 1 stopLGAMDW
9:26pmChicagoThu, Nov 12

Round trips

The cheapest return tickets found recently, price for the whole trip.

Plan the rest of the trip

  • Mobile data in United StatesTravel eSIM from $4, installed before you fly.
    Compare plans
  • Getting from the airportTransfers and car hire in Chicago, booked ahead at a fixed price.
    See options
  • Things to do in ChicagoPopular tours from $27.95 per person.
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  • Flight delayed?Delayed or cancelled? See which passenger rights cover this route.
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Price calendar

The lowest one-way fare found for each day over the next 60 days. A dash means no recent fare; you can still pick that day.

October 2026

MoTuWeThFrSaSu1234$1645$1366–7$1288$1559$18410$13111$13712$13813$13314$13915$13116$14517$16118$17719$14020$14421$13222$12823$15924–25$14926$14727$11828$11829$13730–31–

November 2026

MoTuWeThFrSaSu1$1552$1483–4–5–6$1507–8$1299–10–11$11812$12513–14–15$14516$14417–18$10319–20$13921–22–23–24–25–26–27–28–29–30–

December 2026

MoTuWeThFrSaSu1–2–345678910111213141516171819202122232425262728293031
$132 or lessGreen: the cheapest fifth of fares on this route. Lowest in these 60 days: Nov 18, $103.

Lowest fares by month

In the fares found this week, November has the lowest: from $103 one-way, against $166 in May 2027. Pick a month to see its cheapest date.

$0$100$200Oct$103NovDecJanFebMarAprMayJunJulAugSep
Show as a table
MonthCheapest one-wayDateStops
October$118Tue, Oct 271 stop
November$103Wed, Nov 181 stop
December$138Wed, Dec 16Nonstop
January 2027$148Fri, Jan 1Nonstop
February 2027—
March 2027$151Mon, Mar 1Nonstop
April 2027$164Mon, Apr 12Nonstop
May 2027$166Wed, May 5Nonstop
June 2027$164Sun, Jun 6Nonstop
July 2027—
August 2027$165Thu, Aug 5Nonstop
September 2027—

Questions travellers ask

What is the cheapest month to fly from New York to Chicago?

In the fares found this week, November has the lowest: from $103 one-way, against $166 in May 2027.

Are there direct flights from New York to Chicago?

Yes. Recent fares include nonstop flights with American Airlines, Southwest Airlines, United Airlines and jetBlue.

How long is the flight from New York to Chicago?

A nonstop flight takes about 2h 25m. The distance is 731 mi.

Which day of the week is cheapest to fly?

In the fares we have, Tuesday departures are the cheapest, with a typical lowest fare of $133. Saturday is the priciest at about $161.

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