Cheap flights from New York to Chicago from $113 EWR, JFK, LGA → MDW, ORD, RFD

Found recently, and the cheapest we hold

It is also the cheapest return we hold, of any age.

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $114 to $244.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other 7-night return fares leaving within 3 days of 2 Dec to compare.

Every date we hold

558 fares on 38 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $193.

Found recently, and the cheapest we hold

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $84 to $129.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other one-way fares leaving within 3 days of 21 Nov to compare.

Every date we hold

218 fares on 23 departure dates

Which month looks cheapest?

November 2026 is the cheapest month — from $99.

Return

Fares 30 to 59 days before departure were typically 32% lower than 0 to 6 days before departure.

From the cheapest return each day between 24 Sept and 11 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

One-way

Fares 14 to 29 days before departure were typically 20% lower than 0 to 6 days before departure.

From the cheapest one-way each day between 24 Sept and 11 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

How much is a return flight from New York to Chicago?

The cheapest return found recently is $193 with Frontier Airlines, 2 Dec to 9 Dec, found yesterday. The cheapest return fare on each of 38 departure dates is usually $317 to $363.

How much is a one-way flight from New York to Chicago?

The cheapest one-way found recently is $113 with American Airlines, 21 Nov, found 2 days ago. The cheapest one-way we hold, of any age, is $99 with American Airlines, 15 Nov, found 8 days ago. The cheapest one-way fare on each of 23 departure dates is usually $126 to $180.

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

December 2026 is the cheapest month for a return, from $193, 2 Dec to 9 Dec, found yesterday. November 2026 is the cheapest month for a one-way, from $99, 15 Nov, found 8 days ago.

Every date in December 2026

Every date in November 2026

How far ahead should I book a flight from New York to Chicago?

In 49 days of prices between 24 Sept and 11 Nov, return fares 30 to 59 days before departure were typically 32% lower than 0 to 6 days before departure. One-way fares 14 to 29 days before departure were typically 20% lower than 0 to 6 days before departure.

Is there a direct flight from New York to Chicago?

Yes, the cheapest nonstop return found recently is $261 with United Airlines, 28 Jan 2027 to 1 Feb 2027, found 2 days ago. The cheapest nonstop one-way found recently is $113 with American Airlines, 21 Nov, found 2 days ago.

Every nonstop date from New York to Chicago

How long is the flight from New York to Chicago?

The cheapest nonstop one-way found recently, with American Airlines on 21 Nov, takes 3 h 8 min from Newark Liberty International Airport (EWR) to O'Hare International Airport (ORD).

Which airlines have the cheapest flights from New York to Chicago?

Between 13 Nov and 9 Oct 2027, American Airlines has the cheapest return on 18 of the 38 departure dates we hold, Frontier Airlines on 11 and United Airlines on 6. Between 15 Nov and 9 Oct 2027, American Airlines has the cheapest one-way on 13 of the 23 departure dates we hold, Frontier Airlines on 6 and United Airlines on 4.