Discover the Best Cheap Flight Deals from Chicago

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Latest cheap flight deals departing from Chicago.

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What is a premium fare? Airfare that is greater than 60% off the normal ticket price as well as airfare deals to top destinations such as Hawaii and Alaska.

Flights Options

Departure Airport(s)
Destination Airport(s)
Departure Country Pro Only
Destination Country Pro Only
Flights Under Pro Only

$192

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Jan - Feb 2023
💰 $96

🇺🇸 Chicago, United States
🇲🇽 Cancun, Mexico

Travel Between:

$645

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Sep - Oct 2023
💰 $322

🇺🇸 Chicago, United States
🇮🇳 New Delhi, India

Travel Between:

$169

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Jan - Feb 2023
💰 $84

🇺🇸 Chicago, United States
🇩🇴 Punta Cana, Dominican Republic

Travel Between:

$192

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Jan - Feb 2023
💰 $96

🇺🇸 Chicago, United States
🇲🇽 Cancun, Mexico

Travel Between:

$645

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Sep - Oct 2023
💰 $322

🇺🇸 Chicago, United States
🇮🇳 New Delhi, India

Travel Between:

$169

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Jan - Feb 2023
💰 $84

🇺🇸 Chicago, United States
🇩🇴 Punta Cana, Dominican Republic

Travel Between:

$135

*** - *** 2021
💰 $148 📅

🇺🇸 Chicago, United States
🇺🇸 Nashville, United States

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$148

*** - *** 2021
💰 $2,095 📅

🇺🇸 Chicago, United States
🇺🇸 Houston, United States

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$206

*** - *** 2021
💰 $169 📅

🇺🇸 Chicago, United States
🇺🇸 Portland, United States

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$112

*** - *** 2021
💰 $150 📅

🇺🇸 Chicago, United States
🇺🇸 Fort Myers, United States

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$217

*** - *** 2021
💰 $90 📅

🇺🇸 Chicago, United States
🇺🇸 Seattle, United States

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$502

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Jan - Feb 2022 / Jan - Jan 2022 / Apr - May 2022 / Feb - Feb 2022 / May - May 2022
💰 $498

🇺🇸 Chicago, United States
🇮🇹 Napoli, Italy

Travel Between: January 13th, 2022 - May 12th, 2022

$366

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Mar - Mar 2022 / Feb - Mar 2022 / May - May 2022 / Apr - Apr 2022 / Jan - Feb 2022 / Jan - Jan 2022
💰 $334

🇺🇸 Chicago, United States
🇺🇸 Honolulu, United States

Travel Between: January 10th, 2022 - May 10th, 2022

$291

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Feb - Mar 2022 / Feb - Feb 2022 / Mar - Apr 2022 / Mar - Mar 2022 / Apr - May 2022 / Apr - Apr 2022 / Sep - Sep 2022 / May - May 2022
💰 $359

🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia

Travel Between: February 2nd, 2022 - September 20th, 2022

$210

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Jan - Feb 2022 / Jan - Jan 2022 / Feb - Mar 2022 / Jan - Feb 2022 / Mar - Mar 2022
💰 $290

🇺🇸 Chicago, United States
🇺🇸 San Jose, United States

Travel Between: January 15th, 2022 - March 8th, 2022

$299

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Jan - Jan 2022 / Mar - Mar 2022 / Feb - Feb 2022 / Sep - Sep 2022 / Aug - Aug 2022
💰 $351

🇺🇸 Chicago, United States
🇪🇨 Quito, Ecuador

Travel Between: January 18th, 2022 - September 28th, 2022

$115

*** - *** 2021
💰 $264 📅

🇺🇸 Chicago, United States
🇺🇸 Dallas, United States

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$190

*** - *** 2021
💰 $206 📅

🇺🇸 Chicago, United States
🇺🇸 Charlottesville, United States

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$476

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Jan - Feb 2022 / Apr - May 2022 / Mar - Mar 2022 / Oct - Oct 2022 / Sep - Sep 2022
💰 $424

🇺🇸 Chicago, United States
🇬🇧 London, United Kingdom

Travel Between: January 23rd, 2022 - October 20th, 2022

$103

*** - *** 2021
💰 $794 📅

🇺🇸 Chicago, United States
🇺🇸 Orlando, United States

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$115

*** - *** 2021
💰 $151 📅

🇺🇸 Chicago, United States
🇺🇸 Cleveland, United States

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$163

*** - *** 2021
💰 $57 📅

🇺🇸 Chicago, United States
🇺🇸 Los Angeles, United States

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$197

*** - *** 2021
💰 $182 📅

🇺🇸 Chicago, United States
🇺🇸 Wichita, United States

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$258

*** - *** 2021
💰 $135 📅

🇺🇸 Chicago, United States
🇺🇸 Pensacola, United States

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