Cheap flights from Chicago to New York from $96 MDW, ORD, RFD → EWR, JFK, LGA

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 $130 to $233.

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

Could nearby dates be cheaper?

We hold no other 6-night return fares leaving within 3 days of 3 Feb 2027 to compare.

Every date we hold

719 fares on 37 departure dates

Which month looks cheapest?

February 2027 is the cheapest month — from $195.

Found recently, and the cheapest we hold

It is also the cheapest one-way we hold, of any age.

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $89 to $130.

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

Could nearby dates be cheaper?

No. We hold one-way fares on 3 other departure dates within 3 days of 19 Nov, and none is cheaper.

Every date we hold

178 fares on 23 departure dates

Which month looks cheapest?

November 2026 is the cheapest month — from $96.

Return

Fares 30 to 59 days before departure were typically 24% 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 10% 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 Chicago to New York?

The cheapest return found recently is $195 with Frontier Airlines, 3 Feb 2027 to 9 Feb 2027, found yesterday. The cheapest return fare on each of 37 departure dates is usually $268 to $345.

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

The cheapest one-way found recently is $96 with Frontier Airlines, 19 Nov, found 2 days ago. The cheapest one-way fare on each of 23 departure dates is usually $141 to $180.

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

February 2027 is the cheapest month for a return, from $195, 3 Feb 2027 to 9 Feb 2027, found yesterday. November 2026 is the cheapest month for a one-way, from $96, 19 Nov, found 2 days ago.

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

In 49 days of prices between 24 Sept and 11 Nov, return fares 30 to 59 days before departure were typically 24% lower than 0 to 6 days before departure. One-way fares 14 to 29 days before departure were typically 10% lower than 0 to 6 days before departure.

Is there a direct flight from Chicago to New York?

Yes, the cheapest nonstop return found recently is $312 with American Airlines, 5 Dec to 7 Dec, found 2 days ago. The cheapest nonstop one-way found recently is $226 with Southwest Airlines, 19 Nov, found 2 days ago.

Every nonstop date from Chicago to New York

How long is the flight from Chicago to New York?

The cheapest nonstop one-way found recently, with Southwest Airlines on 19 Nov, takes 2 h 5 min from Chicago Midway International Airport (MDW) to LaGuardia Airport (LGA).

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

Between 14 Nov and 7 Oct 2027, Frontier Airlines has the cheapest return on 15 of the 37 departure dates we hold, United Airlines on 11 and American Airlines on 11. Between 17 Nov and 9 Oct 2027, Frontier Airlines has the cheapest one-way on 12 of the 23 departure dates we hold, American Airlines on 5 and Allegiant Air on 3.