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)

$290

View Deal
Nov - Dec 2021
💰 $145

🇺🇸 Chicago, United States
🇵🇹 Lisbon, Portugal

Travel Between: Availability from November to December 2021

$376

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Dec - Mar 2022
💰 $188

🇺🇸 Chicago, United States
🇵🇪 Lima, Peru

Travel Between: Availability from December 2021 to March 2022

$215

*** - *** 2021
💰 $149 📅

🇺🇸 Chicago, United States
🇺🇸 Fort Lauderdale, United States

Travel Between: ⚡ Upgrade to premium plan to get access to travel dates and more.

$405

*** - *** 2021
💰 $141 📅

🇺🇸 Chicago, United States
🇺🇸 Boise, United States

Travel Between: ⚡ Upgrade to premium plan to get access to travel dates and more.

$299

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Aug - Apr 2022
💰 $149

🇺🇸 Chicago, United States
🇪🇨 Quito, Ecuador

Travel Between: Availability from August 2021 to April 2022 (excluding Christmas/New Year)

$675

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Oct - May 2022
💰 $337

🇺🇸 Chicago, United States
🇲🇻 Male, Maldives

Travel Between: Availability from October 2021 to May 2022 (excluding Christmas/New Year)

$132

*** - *** 2021
💰 $66

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

Travel Between: ⚡ Upgrade to premium plan to get access to travel dates and more.

$102

*** - *** 2021
💰 $51

🇺🇸 Chicago, United States
🇺🇸 San Francisco, United States

Travel Between: ⚡ Upgrade to premium plan to get access to travel dates and more.

$100

*** - *** 2021
💰 $50

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

Travel Between: ⚡ Upgrade to premium plan to get access to travel dates and more.

$68

*** - *** 2021
💰 $34

🇺🇸 Chicago, United States
🇺🇸 Fort Lauderdale, United States

Travel Between: ⚡ Upgrade to premium plan to get access to travel dates and more.

$391

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Sep - Mar 2022
💰 $195

🇺🇸 Chicago, United States
🇩🇪 Berlin, Germany

Travel Between: Availability from September 2021 to March 2022

$198

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Sep - Oct 2021
💰 $99

🇺🇸 Chicago, United States
🇲🇽 Cancun, Mexico

Travel Between: Limited availability from September to October 2021

$335

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Oct - Oct 2021
💰 $167

🇺🇸 Chicago, United States
🇩🇰 Copenhagen, Denmark

Travel Between: Limited availability in October 2021

$392

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Nov - Dec 2021
💰 $196

🇺🇸 Chicago, United States
🇩🇰 Copenhagen, Denmark

Travel Between: Availability from November to December 2021

$659

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Oct - Dec 2021
💰 $329

🇺🇸 Chicago, United States
🇿🇦 Cape Town, South Africa

Travel Between: Availability from October to December 2021

$237

*** - *** 2021
💰 $276 📅

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

Travel Between: ⚡ Upgrade to premium plan to get access to travel dates and more.

$278

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Aug - Mar 2022
💰 $139

🇺🇸 Chicago, United States
🇮🇪 Dublin, Ireland

Travel Between: Availability from August 2021 to March 2022 (excluding Christmas)

$675

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Oct - Apr 2022
💰 $337

🇺🇸 Chicago, United States
🇲🇻 Male, Maldives

Travel Between: Availability from October 2021 to April 2022 (excluding Christmas/New Year)

$648

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Oct - Dec 2021
💰 $324

🇺🇸 Chicago, United States
🇦🇪 Dubai, United Arab Emirates

Travel Between: Availability from October to December 2021

$608

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Aug - May 2022
💰 $304

🇺🇸 Chicago, United States
🇰🇪 Nairobi, Kenya

Travel Between: Availability from August 2021 to May 2022 (excluding Christmas/New Year)

$440

*** - *** 2021
💰 $169 📅

🇺🇸 Chicago, United States
🇺🇸 Buffalo, United States

Travel Between: ⚡ Upgrade to premium plan to get access to travel dates and more.

$375

*** - *** 2021
💰 $287 📅

🇺🇸 Chicago, United States
🇺🇸 San Antonio, United States

Travel Between: ⚡ Upgrade to premium plan to get access to travel dates and more.

$672

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Sep - Nov 2021
💰 $336

🇺🇸 Chicago, United States
🇿🇦 Johannesburg, South Africa

Travel Between: Availability from September to November 2021

$535

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Sep - May 2022
💰 $267

🇺🇸 Chicago, United States
🇭🇰 Hong Kong, Hong Kong

Travel Between: Availability from September 2021 to May 2022 (excluding Christmas/New Year)
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