Cheapest one-way flights from Tampa to Chicago in January from $98

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

One-Way flights

24 Jan Southwest Airlines direct
17 Jan Southwest Airlines direct
31 Jan Delta
31 Jan Southwest Airlines direct
16 Jan Southwest Airlines direct
01 Jan Delta
05 Jan Southwest Airlines direct
01 Jan Southwest Airlines direct
04 Jan Southwest Airlines
04 Jan Frontier Airlines direct

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

Skyscanner

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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