Flights from Chicago

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Flight guides from Chicago

Airline comparisons, cheapest months, and insider booking tips by destination.

Chicago→Amsterdam

KLM Royal Dutch Airlines, Delta Air Lines · from $540

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Chicago→Cancún

United Airlines, American Airlines · from $229

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Chicago→Dublin

Aer Lingus (EI), United Airlines · from $520

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Chicago→Las Vegas

Southwest Airlines, American Airlines · from $169

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Chicago→London

American Airlines, United Airlines · from $590

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Chicago→Miami

American Airlines, United Airlines · from $91

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Chicago→Rome

United, ITA Airways · from $640

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Chicago→Tokyo

ANA (All Nippon Airways), Japan Airlines (JAL) · from $920

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Hotel deals at your destination

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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 from Chicago

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✈️ All flight guides from Chicago

Destination hubs, travel tips, and city guides.

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