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

$392

View Deal
Jan - Mar 2023
💰 $196

🇺🇸 Chicago, United States
🇮🇪 Dublin, Ireland

Travel Between: Availability from January to March 2023

$269

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Oct - Feb 2023
💰 $134

🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico

Travel Between: Availability from October 2022 to February 2023 (excluding Christmas/New Year)

$178

*** - *** 2022
💰 $89

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

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

$281

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Sep - Oct 2022
💰 $140

🇺🇸 Chicago, United States
🇲🇽 Cozumel, Mexico

Travel Between: Availability from September to October 2022

$587

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Oct - Dec 2022
💰 $293

🇺🇸 Chicago, United States
🇷🇼 Kigali, Rwanda

Travel Between: Availability from October to December 2022

$424

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Feb - May 2023
💰 $212

🇺🇸 Chicago, United States
🇵🇹 Porto, Portugal

Travel Between: Availability from February to May 2023

$361

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Jan - Mar 2023
💰 $180

🇺🇸 Chicago, United States
🇪🇨 Quito, Ecuador

Travel Between: Availability from January to March 2023

$515

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Apr - May 2023
💰 $257

🇺🇸 Chicago, United States
🇱🇧 Beirut, Lebanon

Travel Between: Availability from April to May 2023

$341

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Jan - Mar 2023
💰 $170

🇺🇸 Chicago, United States
🇵🇹 Lisbon, Portugal

Travel Between: Availability from January to February 2023

$338

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Dec - Apr 2023
💰 $169

🇺🇸 Chicago, United States
🇵🇹 Lisbon, Portugal

Travel Between: Availability from December 2022 to April 2023 (excluding Christmas/New Year)

$280

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Aug - Sep 2022
💰 $140

🇺🇸 Chicago, United States
🇲🇽 Cozumel, Mexico

Travel Between: Availability from August to September 2022

$382

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Nov - Jun 2023
💰 $191

🇺🇸 Chicago, United States
🇩🇰 Copenhagen, Denmark

Travel Between: Availability from November 2022 to June 2023 (excluding Christmas/New Year)

$343

*** - *** 2023
💰 $171

🇺🇸 Chicago, United States
🇺🇸 Kahului, United States

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

$360

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Oct - May 2023
💰 $180

🇺🇸 Chicago, United States
🇪🇨 Quito, Ecuador

Travel Between: Availability from October 2022 to May 2023 (excluding Christmas/New Year)

$343

View Deal
Oct - Apr 2023
💰 $171

🇺🇸 Chicago, United States
🇵🇹 Lisbon, Portugal

Travel Between: Availability from October 2022 to April 2023 (excluding Christmas/New Year)

$340

View Deal
Oct - May 2023
💰 $170

🇺🇸 Chicago, United States
🇵🇹 Lisbon, Portugal

Travel Between: Availability from October 2022 to May 2023 (excluding Christmas/New Year)

$637

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Oct - Mar 2023
💰 $318

🇺🇸 Chicago, United States
🇪🇬 Hurghada, Egypt

Travel Between: Availability from October 2022 to March 2023 (excluding Christmas/New Year)

$561

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Sep - May 2023
💰 $280

🇺🇸 Chicago, United States
🇷🇼 Kigali, Rwanda

Travel Between: Availability from September 2022 to May 2023 (excluding Christmas/New Year)

$178

*** - *** 2022
💰 $89

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

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

$368

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Oct - Nov 2022
💰 $184

🇺🇸 Chicago, United States
🇸🇷 Paramaribo, Suriname

Travel Between: Availability from September to November 2022

$379

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Jan - Apr 2023
💰 $189

🇺🇸 Chicago, United States
🇮🇹 Milan, Italy

Travel Between: Availability from January to April 2023

$520

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Mar - Apr 2023
💰 $260

🇺🇸 Chicago, United States
🇱🇧 Beirut, Lebanon

Travel Between: Availability from March to April 2023

$560

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Jan - May 2023
💰 $280

🇺🇸 Chicago, United States
🇪🇬 Cairo, Egypt

Travel Between: Availability from January to February 2023

$398

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Jan - May 2023
💰 $199

🇺🇸 Chicago, United States
🇳🇱 Amsterdam, Netherlands

Travel Between: Availability from January to May 2023
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