Cheap flights from Chicago MDW

Showing you the latest cheap flights deals for Chicago (MDW) sourced from all around the web. Let's get ready to travel.

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October 26, 2021
SUMMER: Chicago to Cartagena, Colombia for only $395 roundtrip
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October 25, 2021
Chicago to Malaga, Spain for only $329 roundtrip
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October 25, 2021
American: Chicago – Cancun, Mexico. $160 (Basic Economy) / $180 (Regular Economy). Roundtrip, including all Taxes
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October 25, 2021
SUMMER: Chicago to Bogota, Colombia for only $304 roundtrip
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October 24, 2021
Non-stop from Chicago to Orlando, Florida (& vice versa) for only $97 roundtrip
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October 24, 2021
Warsaw, Poland to Chicago, USA for only €271 roundtrip
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October 24, 2021
American: Chicago – Las Vegas (and vice versa). $97. Roundtrip, including all Taxes
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October 23, 2021
Chicago to Quito, Ecuador for only $315 roundtrip
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October 23, 2021
SUMMER: Chicago to Lima, Peru for only $363 roundtrip
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October 23, 2021
Non-stop from Chicago to Denver, Colorado (& vice versa) for only $97 roundtrip
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October 23, 2021
Chicago or Austin to Cozumel, Mexico from only $196 roundtrip
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October 23, 2021
American: Chicago – Denver (and vice versa). $97. Roundtrip, including all Taxes
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