Cheap flights from Chicago to Dallas from $107 MDW, ORD, RFD → DAL, DFW

Found recently, and the cheapest we hold

What have prices looked like?

Over 50 days, 24 Sept to 12 Nov, the cheapest return we saw each day was $109 to $283.

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

Could nearby dates be cheaper?

We hold no other 2-night return fares leaving within 3 days of 14 Nov to compare.

Every date we hold

86 fares on 5 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $163.

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 50 days, 24 Sept to 12 Nov, the cheapest one-way we saw each day was $45 to $137.

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 18 Jan 2027 to compare.

Every date we hold

5 fares on 3 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $107.

Return

Fares 60 to 89 days before departure were typically 45% lower than 0 to 6 days before departure.

From the cheapest return each day between 24 Sept and 12 Nov (50 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 49% lower than 0 to 6 days before departure.

From the cheapest one-way each day between 24 Sept and 12 Nov (50 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 Dallas?

The cheapest return found recently is $262 with Frontier Airlines, 14 Nov to 16 Nov, found yesterday. The cheapest return we hold, of any age, is $163 with Frontier Airlines, 4 Dec to 7 Dec, found 5 days ago. The cheapest return fare on each of 5 departure dates is usually $225 to $262.

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

The cheapest one-way found recently is $107 with Frontier Airlines, 18 Jan 2027, found yesterday. The cheapest one-way fare on each of 3 departure dates is usually $120 to $138.

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

December 2026 is the cheapest month for a return, from $163, 4 Dec to 7 Dec, found 5 days ago. January 2027 is the cheapest month for a one-way, from $107, 18 Jan 2027, found yesterday.

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

In 50 days of prices between 24 Sept and 12 Nov, return fares 60 to 89 days before departure were typically 45% lower than 0 to 6 days before departure. One-way fares 14 to 29 days before departure were typically 49% lower than 0 to 6 days before departure.

Is there a direct flight from Chicago to Dallas?

Yes, the cheapest nonstop return found recently is $262 with Frontier Airlines, 14 Nov to 16 Nov, found yesterday. The cheapest nonstop one-way found recently is $132 with Frontier Airlines, 18 Nov, found today.

How long is the flight from Chicago to Dallas?

The cheapest nonstop one-way found recently, with Frontier Airlines on 18 Nov, takes 2 h 42 min from Chicago Midway International Airport (MDW) to Dallas/Fort Worth International Airport (DFW). The cheapest one-way found recently, with Frontier Airlines on 18 Jan 2027, takes 18 h 45 min with 1 stop.

Which airlines have the cheapest flights from Chicago to Dallas?

Between 14 Nov and 18 Dec, Frontier Airlines has the cheapest return on all 5 departure dates we hold. Between 18 Nov and 18 Jan 2027, Frontier Airlines has the cheapest one-way on all 3 departure dates we hold.