Cheap flights from Dallas to Chicago from $112 DAL, DFW → 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 $90 to $269.

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 9 Dec to compare.

Every date we hold

209 fares on 17 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $120.

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 $49 to $145.

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 27 Dec to compare.

Every date we hold

6 fares on 3 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $58.

Return

Fares 14 to 29 days before departure were typically 52% 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 30 to 59 days before departure were typically 49% 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 Dallas to Chicago?

The cheapest return found recently is $143 with Frontier Airlines, 9 Dec to 16 Dec, found yesterday. The cheapest return we hold, of any age, is $120 with Frontier Airlines, 3 Dec to 4 Dec, found 8 days ago. The cheapest return fare on each of 17 departure dates is usually $181 to $281.

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

The cheapest one-way found recently is $112 with Frontier Airlines, 27 Dec, found 3 days ago. The cheapest one-way we hold, of any age, is $58 with Frontier Airlines, 16 Dec, found 7 days ago. The cheapest one-way fare on each of 3 departure dates is usually $85 to $143.

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

December 2026 is the cheapest month for a return, from $120, 3 Dec to 4 Dec, found 8 days ago. It is the cheapest month for a one-way too, from $58, 16 Dec, found 7 days ago.

Every date in December 2026

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

In 49 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 52% lower than 0 to 6 days before departure. One-way fares 30 to 59 days before departure were typically 49% lower than 0 to 6 days before departure.

Is there a direct flight from Dallas to Chicago?

Yes, the cheapest nonstop return found recently is $158 with Frontier Airlines, 14 Dec to 16 Dec, found 2 days ago. The cheapest nonstop one-way found recently is $112 with Frontier Airlines, 27 Dec, found 3 days ago.

Every nonstop date from Dallas to Chicago

How long is the flight from Dallas to Chicago?

The cheapest nonstop one-way found recently, with Frontier Airlines on 27 Dec, takes 2 h 32 min from Dallas/Fort Worth International Airport (DFW) to O'Hare International Airport (ORD).

Which airlines have the cheapest flights from Dallas to Chicago?

Between 20 Nov and 1 Jun 2027, Frontier Airlines has the cheapest return on 16 of the 17 departure dates we hold, and Southwest Airlines on 1. Between 16 Dec and 24 Apr 2027, Frontier Airlines has the cheapest one-way on 2 of the 3 departure dates we hold, and Contour Airlines on 1.