Cheapest return flights from Dallas-Fort Worth to Chicago in January from $58

AirHint found the following cheapest return flights from Dallas-Fort Worth (DFW) to Chicago (MDW) in January 2026 (see full year).

Return flights

26 Jan - 02 Feb Frontier Airlines direct
31 Jan - 02 Feb Frontier Airlines
22 Jan - 26 Jan Frontier Airlines
29 Jan - 02 Feb Frontier Airlines
23 Jan - 26 Jan Frontier Airlines direct
29 Jan - 14 Feb Frontier Airlines
29 Jan - 03 Feb Southwest Airlines direct
29 Jan - 04 Feb Southwest Airlines direct
29 Jan - 05 Feb Southwest Airlines direct
29 Jan - 02 Feb Southwest Airlines direct
29 Jan - 08 Feb Frontier Airlines
30 Jan - 05 Feb Frontier Airlines
29 Jan - 31 Jan Frontier Airlines
23 Jan - 30 Jan Frontier Airlines
23 Jan - 30 Jan Frontier Airlines direct
29 Jan - 31 Jan Southwest Airlines direct
25 Jan - 28 Jan Frontier Airlines
15 Jan - 17 Jan Frontier Airlines
16 Jan - 17 Jan Frontier Airlines
14 Jan - 21 Jan Spirit Airlines

Also check the deals for one-way flights from Dallas-Fort Worth to Chicago in January.

Powered by

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

Book a cheap hotel in Chicago

Cheap car rent in Chicago

Feel free to contact us with any feedback or request another flight research.