Flights to Chicago

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Flight guides to Chicago

Airline comparisons, booking tips, and insider advice by route.

New York→Chicago

JetBlue, American Airlines · from $98

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Cheapest flights to Chicago this month

Best prices from major US departure cities — updated daily.

New York → ChicagoJFK
$162
Wed, Jul 22 · Direct · B6
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Los Angeles → ChicagoLAX
$218
Sat, Aug 1 · F9
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Lowest return fares per departure city · Final prices confirmed at booking

Hotel deals in Chicago

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🏨
-78% off

Mystery Getaway: Surprise Destination with Flights & Hotel

$199$899
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🏨
-77% off

Great Wolf Lodge Minneapolis: Suites with Daily Waterpark Passes

$121$528
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🏨
-74% off

4.5-Star Historic Hotel in Wilmington featuring a 4-Star Restaurant

$211$800
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🏨
-71% off

4-Star Resort in Downtown Palm Springs

$192$651
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🏨 Hotels in Chicago

Compare hotel prices from 10+ booking sites.

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🎯 Things to do in Chicago

Tours, attractions, and activities in Chicago.

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