Discover the Best Cheap Flight Deals from Chicago

We collect cheap flight deals from around the web, and provide our subscribers a more personalized flight deals feed, straight to their inbox. Join over 100,000 subscribers.

(Don't live in Chicago?)

Showing flight deals from Chicago

Latest cheap flight deals departing from Chicago.

âš¡ Unlock Premium Fares by upgrading today!

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

$348

View Deal
Sep - Oct 2023
💰 $174

🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia

Travel Between: Availability from September to October 2023

$329

View Deal
Aug - Oct 2023
💰 $164

🇺🇸 Chicago, United States
🇨🇴 Cartagena, Colombia

Travel Between: Availability from August to October 2023

$148

*** - *** 2023
💰 $74 ⚡

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

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

$202

View Deal
Oct - Nov 2023
💰 $101

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

Travel Between: Limited availability from October to November 2023

$354

View Deal
May - Feb 2024
💰 $177

🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia

Travel Between: Availability from May 2023 to February 2024 (excluding Christmas/New Year)

$380

View Deal
Nov - Feb 2024
💰 $190

🇺🇸 Chicago, United States
🇫🇷 Paris, France

Travel Between: Limited availability from November 2023 to February 2024 (excluding Christmas/New Year)

$251

View Deal
Apr - May 2023
💰 $125

🇺🇸 Chicago, United States
🇲🇽 Cancun, Mexico

Travel Between: Availability from April to May 2023

$297

View Deal
Sep - Oct 2023
💰 $148

🇺🇸 Chicago, United States
🇲🇽 Mexico City, Mexico

Travel Between: Availability from September to October 2023

$148

*** - *** 2023
💰 $74 ⚡

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

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

$106

*** - *** 2023
💰 $53 ⚡

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

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

$366

View Deal
May - May 2023
💰 $183

🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia

Travel Between: Availability in May 2023

$182

View Deal
Oct - Nov 2023
💰 $91

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

Travel Between: Availability from October to November 2023

$251

View Deal
Apr - Oct 2023
💰 $125

🇺🇸 Chicago, United States
🇲🇽 Cancun, Mexico

Travel Between: Availability from April to October 2023 (excluding summer)

$293

View Deal
Aug - Nov 2023
💰 $146

🇺🇸 Chicago, United States
🇲🇽 Mexico City, Mexico

Travel Between: Availability from August to November 2023

$293

View Deal
Aug - Nov 2023
💰 $146

🇺🇸 Chicago, United States
🇲🇽 Mexico City, Mexico

Travel Between: Availability from August to November 2023

$294

View Deal
Sep - Nov 2023
💰 $147

🇺🇸 Chicago, United States
🇵🇷 Ponce, Puerto Rico

Travel Between: Availability from September to November 2023

$294

View Deal
Sep - Nov 2023
💰 $147

🇺🇸 Chicago, United States
🇵🇷 Ponce, Puerto Rico

Travel Between: Availability from September to November 2023

$248

*** - *** 2023
💰 $124 ⚡

🇺🇸 Chicago, United States
🇺🇸 Anchorage, United States

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

$248

*** - *** 2023
💰 $124 ⚡

🇺🇸 Chicago, United States
🇺🇸 Anchorage, United States

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

$547

View Deal
Jan - Jan 2024
💰 $273

🇺🇸 Chicago, United States
🇲🇦 Casablanca, Morocco

Travel Between: Availability in January 2024

$349

View Deal
Apr - May 2023
💰 $174

🇺🇸 Chicago, United States
🇨🇴 Cartagena, Colombia

Travel Between: Limited availability from April to May 2023

$337

View Deal
Nov - Nov 2023
💰 $168

🇺🇸 Chicago, United States
🇮🇪 Dublin, Ireland

Travel Between: Availability in November 2023

$273

View Deal
Apr - May 2023
💰 $136

🇺🇸 Chicago, United States
🇲🇽 Cancun, Mexico

Travel Between: Availability from April to May 2023

$387

View Deal
Oct - Nov 2023
💰 $193

🇺🇸 Chicago, United States
🇨🇴 Barranquilla, Colombia

Travel Between: Limited availability from October to November 2023
Loading...