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Route

New York to Chicago: what the flight costs

By the VacayMatch editors · Updated

In the last 60 days we checked this route 23 times. The typical return was £274 per person and the lowest £243, taxes and fees included.

Per person
Lowest seen£243
Typical (median)£274
Price checks, 60 days23

Check live prices

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Trips we picked on this route

Next weekend · from New YorkWorth it, if

Chicago

16 – 18 Oct 2026 · 2 nights

  • JetBlue nonstop, 2h 54m, leaving 9:30 AM Friday
  • $345 per person, $18 below the typical fare on this route
  • Club Quarters in The Loop, rated 8.2 from 5,335 reviews
The total, before you go

£1,119 for two · 2 nights · flights, hotel, taxes & fees

Flights £520 + hotel £598, taxes in · a checked bag each adds about £136

JetBlue · nonstop · 2h 54m

The catch: Friday has a 75% chance of rain, and a checked bag is about $180 for two, which is not in the total.

Worth it if you want a city weekend of museums, deep-dish and blues; skip it if you need free cancellation at the value hotel.

Stay from £299/nightThings to do
See the pick

Every fare we found in the last 30 days

CheckedTrip datesPer personAirlineStopsDurationSource
14 Oct 202616 – 18 Oct 2026£260JetBluenonstop2h 54mGoogle Flights
14 Oct 202623 – 25 Oct 2026£430B6 + SYwith a stop2h 55mKiwi.com
14 Oct 202616 – 18 Oct 2026£274B6nonstop2h 54mKiwi.com
14 Oct 202623 – 25 Oct 2026£243Americannonstop2h 49mGoogle Flights
14 Oct 202616 – 18 Oct 2026£260JetBluenonstop2h 54mGoogle Flights
14 Oct 202623 – 25 Oct 2026£302AAwith a stop2h 50mKiwi.com
14 Oct 202616 – 18 Oct 2026£274B6nonstop2h 54mKiwi.com
13 Oct 202623 – 25 Oct 2026£302AAwith a stop2h 50mKiwi.com
13 Oct 202616 – 18 Oct 2026£260JetBluenonstop2h 54mGoogle Flights
13 Oct 202623 – 25 Oct 2026£410B6 + SYwith a stop2h 55mKiwi.com
13 Oct 202616 – 18 Oct 2026£274B6nonstop2h 54mKiwi.com
13 Oct 202616 – 18 Oct 2026£260Americannonstop2h 49mGoogle Flights
13 Oct 202623 – 25 Oct 2026£418B6with a stop2h 54mKiwi.com
13 Oct 202616 – 18 Oct 2026£274B6nonstop2h 54mKiwi.com
12 Oct 202623 – 25 Oct 2026£375B6 + F9with a stop2h 54mKiwi.com
11 Oct 202623 – 25 Oct 2026£254Unitednonstop2h 48mGoogle Flights
11 Oct 202623 – 25 Oct 2026£254Unitednonstop2h 48mGoogle Flights
11 Oct 202616 – 18 Oct 2026£274B6nonstop5h 14mKiwi.com
11 Oct 202616 – 18 Oct 2026£274B6nonstop5h 14mKiwi.com
11 Oct 202623 – 25 Oct 2026£340B6 + F9with a stop2h 54mKiwi.com
11 Oct 202616 – 18 Oct 2026£274B6nonstop2h 54mKiwi.com
11 Oct 202623 – 25 Oct 2026£340B6 + F9with a stop2h 54mKiwi.com
11 Oct 202616 – 18 Oct 2026£274B6nonstop2h 54mKiwi.com

About Chicago

Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.

Chicago from every city: when to go, where to stay, what to do

Questions about New York to Chicago

What does a return from New York to Chicago usually cost?

Over the last 60 days the typical price we found was £274 per person, taxes and fees included, across 23 checks; the lowest was £243.

When is the best time to fly from New York to Chicago?

Chicago is at its best in May, June, July, August, September and October. Avoid December, January, February, March: Bitter cold and wind off the lake

Do I need a passport to fly from New York to Chicago?

No passport needed for travellers from the United States: a government photo ID is enough for Chicago.

Prices converted from US dollars at the rate of 15 Oct 2026.

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