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?)

Plan Your Trip with Our Trusted Partners

Booking.com CheapOair

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.

Unlock Premium Fares
Flights Options

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

$455

View Deal
Oct - Oct 2025
💰 $227

🇺🇸 Chicago, United States
🇫🇷 Paris, France

Travel Between:

$589

View Deal
Nov - Nov 2025
💰 $294

🇺🇸 Chicago, United States
🇹🇼 Kaohsiung City, Taiwan

Travel Between:

$424

View Deal
Nov - Nov 2025
💰 $212

🇺🇸 Chicago, United States
🇦🇹 Vienna, Austria

Travel Between:

$386

View Deal
Nov - Nov 2025
💰 $193

🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia

Travel Between:

$367

View Deal
Oct - Oct 2025
💰 $183

🇺🇸 Chicago, United States
🇸🇪 Stockholm, Sweden

Travel Between:

$123

View Deal
Oct - Oct 2025
💰 $61

🇺🇸 Chicago, United States
🇨🇦 Vancouver, Canada

Travel Between:

$405

View Deal
Oct - Oct 2025
💰 $202

🇺🇸 Chicago, United States
🇨🇭 Zurich, Switzerland

Travel Between:

$385

View Deal
Oct - Oct 2025
💰 $192

🇺🇸 Chicago, United States
🇵🇱 Warsaw, Poland

Travel Between:

$456

View Deal
Oct - Oct 2025
💰 $228

🇺🇸 Chicago, United States
🇳🇱 Amsterdam, Netherlands

Travel Between:

$396

View Deal
Jan - Jan 2026
💰 $198

🇺🇸 Chicago, United States
🇮🇹 Milan, Italy

Travel Between:

$631

View Deal
Sep - Sep 2025
💰 $315

🇺🇸 Chicago, United States
🇮🇩 Jakarta, Indonesia

Travel Between:

$254

View Deal
Nov - Nov 2025
💰 $127

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

Travel Between:

$409

View Deal
Nov - Nov 2025
💰 $204

🇺🇸 Chicago, United States
🇺🇸 Lihue, United States

Travel Between:

$199

View Deal
Oct - Oct 2025
💰 $99

🇺🇸 Chicago, United States
🇨🇦 Vancouver, Canada

Travel Between:

$701

View Deal
Nov - Nov 2025
💰 $350

🇺🇸 Chicago, United States
🇹🇼 Kaohsiung City, Taiwan

Travel Between:

$669

View Deal
Nov - Nov 2025
💰 $334

🇺🇸 Chicago, United States
🇹🇼 Taipei, Taiwan

Travel Between:

$657

View Deal
Nov - Nov 2025
💰 $328

🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore

Travel Between:

$117

View Deal
Nov - Nov 2025
💰 $58

🇺🇸 Chicago, United States
🇺🇸 San Diego, United States

Travel Between:

$735

View Deal
Nov - Dec 2025
💰 $367

🇺🇸 Chicago, United States
🇳🇿 Auckland, New Zealand

Travel Between:

$234

View Deal
Oct - Oct 2025
💰 $117

🇺🇸 Chicago, United States
🇳🇮 Managua, Nicaragua

Travel Between:

$408

View Deal
Nov - Nov 2025
💰 $204

🇺🇸 Chicago, United States
🇳🇴 Oslo, Norway

Travel Between:

$450

View Deal
Dec - Dec 2025
💰 $225

🇺🇸 Chicago, United States
🇮🇹 Napoli, Italy

Travel Between:

$749

View Deal
Oct - Oct 2025
💰 $374

🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines

Travel Between:

$474

View Deal
Nov - Nov 2025
💰 $237

🇺🇸 Chicago, United States
🇬🇷 Athens, Greece

Travel Between:
Loading...