Southwest® flights from Tampa to Chicago (O'Hare) from $165*

Fly one-way from Tampa to Chicago (O'Hare) starting at $165. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

$165
OFF

Southwest® Flights From Tampa To Chicago (O'Hare) From $165*

4 weeks from now

Fly one-way from Tampa to Chicago (O'Hare) starting at $165. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

southwest.com

$109
OFF

Southwest Flights To Chicago (CHI) From $109 - KAYAK

4 weeks from now

Southwest flights to Chicago will fly into either Chicago O'Hare Airport, Chicago Midway Airport and Chicago Greater Rockford. ... $165. Search. 2/23 Sun. 2 stops Southwest. 6h 40m ATL …

kayak.com

$155
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Cheap Flights From Tampa To Chicago O'Hare Intl Airport From

4 weeks from now

The cheapest Southwest deal from Tampa to Chicago O'Hare Intl Airport in the last 72 hours was $155 (round-trip), much lower than the average airfare cost of $306 for Southwest flights on …

momondo.com

$46
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$46 Cheap Flights From Tampa To Chicago In 2024/25 - Momondo

4 weeks from now

Search and compare airfare from 1000+ airlines and travel sites to get the cheapest flights from Tampa to Chicago with momondo. ... $165 Southwest. Find Deal. Tue, Nov 19 - Wed, Nov 20. …

momondo.com

$34
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$34 Cheap Flights From Tampa (TPA) To Chicago (CHI) - Expedia

4 weeks from now

Cheap Flights from Tampa (TPA) to Chicago (CHI) start at $34 for one-way and $63 for round trip. Earn your airline miles on top of our rewards!

expedia.com

$44
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$44 Cheap Flights From Tampa (TPA) To Chicago (MDW)

4 weeks from now

Cheap Flights from Tampa (TPA) to Chicago (MDW) start at $44 for one-way and $88 for round trip. Earn your airline miles on top of our rewards!

expedia.com

$53
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Flights From Tampa, FL To Chicago O'Hare Intl Airport (ORD) From …

4 weeks from now

Find airfare and ticket deals for cheap flights from Tampa, FL to Chicago O'Hare Intl Airport (ORD). Search flight deals from various travel partners with one click at $53.

cheapflights.com

$34
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$34 Cheap Flights From Tampa To Chicago (TPA To ORD) - Expedia

4 weeks from now

Cheap Flights from Tampa (TPA) to Chicago (ORD) start at $34 for one-way and $63 for round trip. Earn your airline miles on top of our rewards!

expedia.com

3%
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Cheap Flights From Tampa, FL To Chicago, IL - Kiwi.com

4 weeks from now

Up to 3% cash back · Search, compare, and book flights to Chicago, IL from Tampa, FL. Discover new destinations and unique cheap flights with our easy-to-use search engine and …