Cheap flights from Washington to Chicago from $116 DCA, IAD → MDW, ORD, RFD

Found recently, and the cheapest we hold

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $117 to $302.

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 10 Feb 2027 to compare.

Every date we hold

109 fares on 6 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $201.

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 $62 to $157.

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 6 Dec to compare.

Every date we hold

12 fares on 7 departure dates

Which month looks cheapest?

February 2027 is the cheapest month — from $84.

Return

Fares 14 to 29 days before departure were typically 43% 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 46% 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 Washington to Chicago?

The cheapest return found recently is $214 with Frontier Airlines, 10 Feb 2027 to 14 Feb 2027, found 2 days ago. The cheapest return we hold, of any age, is $201 with Frontier Airlines, 13 Jan 2027 to 22 Jan 2027, found 5 days ago. The cheapest return fare on each of 6 departure dates is usually $225 to $328.

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

The cheapest one-way found recently is $116 with American Airlines, 6 Dec, found 2 days ago. The cheapest one-way we hold, of any age, is $84 with Frontier Airlines, 10 Feb 2027, found 5 days ago. The cheapest one-way fare on each of 7 departure dates is usually $101 to $206.

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

January 2027 is the cheapest month for a return, from $201, 13 Jan 2027 to 22 Jan 2027, found 5 days ago. February 2027 is the cheapest month for a one-way, from $84, 10 Feb 2027, found 5 days ago.

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

In 49 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 43% lower than 0 to 6 days before departure. One-way fares 60 to 89 days before departure were typically 46% lower than 0 to 6 days before departure.

Is there a direct flight from Washington to Chicago?

Yes, the cheapest nonstop return found recently is $389 with Southwest Airlines, 10 Feb 2027 to 14 Feb 2027, found 2 days ago. The cheapest nonstop one-way found recently is $116 with American Airlines, 6 Dec, found 2 days ago.

How long is the flight from Washington to Chicago?

The cheapest nonstop one-way found recently, with American Airlines on 6 Dec, takes 2 h 14 min from Ronald Reagan National Airport (DCA) to O'Hare International Airport (ORD).

Which airlines have the cheapest flights from Washington to Chicago?

Between 27 Nov and 18 May 2027, Frontier Airlines has the cheapest return on 5 of the 6 departure dates we hold, and American Airlines on 1. Between 21 Nov and 9 May 2027, Frontier Airlines has the cheapest one-way on 3 of the 7 departure dates we hold, American Airlines on 2 and Southwest Airlines on 2.