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)

$179

View Deal
Apr - May 2021
💰 $89

🇺🇸 Chicago, United States
🇲🇽 Cancun, Mexico

Travel Between: Availability from April to May 2021

$99

*** - *** 2021
💰 $285 📅

🇺🇸 Chicago, United States
🇺🇸 Savannah, United States

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

$611

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May - Jan 2022
💰 $305

🇺🇸 Chicago, United States
🇮🇱 Tel Aviv, Israel

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

$268

*** - *** 2021
💰 $244 📅

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

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$366

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Jun - Feb 2022
💰 $183

🇺🇸 Chicago, United States
🇵🇪 Lima, Peru

Travel Between: Availability from June 2021 to February 2022 (excluding summer and Christmas/New Year)

$235

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May - Aug 2021
💰 $117

🇺🇸 Chicago, United States
🇲🇽 Cancun, Mexico

Travel Between: Availability from May to August 2021

$259

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Apr - Jun 2021
💰 $129

🇺🇸 Chicago, United States
🇲🇽 Cozumel, Mexico

Travel Between: Availability from April to June 2021

$802

*** - *** 2021
💰 $707 📅

🇺🇸 Chicago, United States
🇲🇽 Puerto Vallarta, Mexico

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

$318

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Jun - Feb 2022
💰 $159

🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia

Travel Between: Availability from June 2021 to February 2022 (excluding Christmas/New Year)

$385

*** - *** 2021
💰 $192

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

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

$566

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Sep - Oct 2021
💰 $283

🇺🇸 Chicago, United States
🇲🇦 Casablanca, Morocco

Travel Between: Availability from September to October 2021

$146

*** - *** 2021
💰 $73

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

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

$94

*** - *** 2021
💰 $172 📅

🇺🇸 Chicago, United States
🇺🇸 Asheville, United States

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

$514

*** - *** 2021
💰 $206 📅

🇺🇸 Chicago, United States
🇺🇸 New York, United States

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$335

*** - *** 2021
💰 $317 📅

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

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$299

*** - *** 2021
💰 $184 📅

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

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$377

*** - *** 2021
💰 $159 📅

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

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$60

*** - *** 2021
💰 $30

🇺🇸 Chicago, United States
🇺🇸 Tampa, United States

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

$60

*** - *** 2021
💰 $30

🇺🇸 Chicago, United States
🇺🇸 Phoenix, United States

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$60

*** - *** 2021
💰 $30

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

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$58

*** - *** 2021
💰 $29

🇺🇸 Chicago, United States
🇺🇸 Austin, United States

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

$60

*** - *** 2021
💰 $30

🇺🇸 Chicago, United States
🇺🇸 Miami, United States

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

$378

View Deal
Jun - Jan 2022
💰 $189

🇺🇸 Chicago, United States
🇨🇴 Barranquilla, Colombia

Travel Between: Availability from June 2021 to January 2022 (excluding Christmas/New Year)

$260

View Deal
Apr - May 2021
💰 $130

🇺🇸 Chicago, United States
🇦🇼 Oranjestad, Aruba

Travel Between: Availability from April to May 2021
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