Cheapest one-way flights from Houston to Chicago in January from $58

AirHint found the following cheapest one-way flights from Houston (HOU) to Chicago (MDW) in January 2026 (see full year).

One-Way flights

10 Jan Southwest Airlines direct
24 Jan Southwest Airlines direct
27 Jan Southwest Airlines direct
22 Jan Frontier Airlines
14 Jan Frontier Airlines
18 Jan Frontier Airlines
03 Jan Frontier Airlines
03 Jan Southwest Airlines direct
04 Jan Frontier Airlines
04 Jan Southwest Airlines direct

Also check the deals for return flights from Houston to Chicago in January.

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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.

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