Cheap flights from Newburgh to Chicago from $305 SWF → 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 $256 to $540.

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

Could nearby dates be cheaper?

We hold no other 4-night return fares leaving within 3 days of 28 Jan 2027 to compare.

Every date we hold

10 fares on 10 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $305.

Found recently, and the cheapest we hold

What have prices looked like?

Over 46 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $157 to $339.

At $351, the cheapest one-way found recently is above that range.

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 25 Apr 2027 to compare.

Every date we hold

8 fares on 8 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $177.

Return

Fares 30 to 59 days before departure were typically 39% 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 60 to 89 days before departure were typically 16% lower than 30 to 59 days before departure.

From the cheapest one-way each day between 24 Sept and 11 Nov (46 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 Newburgh to Chicago?

The cheapest return found recently is $305 with Allegiant Air, 28 Jan 2027 to 1 Feb 2027, found 2 days ago. The cheapest return fare on each of 10 departure dates is usually $363 to $561.

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

The cheapest one-way found recently is $351 with Allegiant Air, 25 Apr 2027, found 2 days ago. The cheapest one-way we hold, of any age, is $177 with Allegiant Air, 24 Jan 2027, found 6 days ago. The cheapest one-way fare on each of 8 departure dates is usually $266 to $384.

What is the cheapest month to fly from Newburgh to Chicago?

January 2027 is the cheapest month for a return, from $305, 28 Jan 2027 to 1 Feb 2027, found 2 days ago. It is the cheapest month for a one-way too, from $177, 24 Jan 2027, found 6 days ago.

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

In 49 days of prices between 24 Sept and 11 Nov, return fares 30 to 59 days before departure were typically 39% lower than 0 to 6 days before departure. In 46 days of prices between 24 Sept and 11 Nov, one-way fares 60 to 89 days before departure were typically 16% lower than 30 to 59 days before departure.

How long is the flight from Newburgh to Chicago?

The cheapest one-way found recently, with Allegiant Air on 25 Apr 2027, takes 27 h 49 min with 1 stop.

Which airlines have the cheapest flights from Newburgh to Chicago?

Between 15 Nov and 28 Jan 2027, Breeze Airways has the cheapest return on 6 of the 10 departure dates we hold, and Allegiant Air on 4. Between 28 Dec and 1 Sept 2027, Allegiant Air has the cheapest one-way on 4 of the 8 departure dates we hold, and Breeze Airways on 4.