To offer you a better browsing experience, we use cookies. By using this site, you agree to our Privacy Policy.
Sign Up

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?)

Recent deals from Chicago:

$455 to 🇳🇱 Amsterdam, Netherlands $398 to 🇳🇴 Oslo, Norway $454 to 🇦🇹 Vienna, Austria See more deals from 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
Mar - Mar 2026
💰 $227
🇺🇸 Chicago, United States
🇳🇱 Amsterdam, Netherlands
Travel Between:

$398

View Deal
Mar - Mar 2026
💰 $199
🇺🇸 Chicago, United States
🇳🇴 Oslo, Norway
Travel Between:

$454

View Deal
Mar - Mar 2026
💰 $227
🇺🇸 Chicago, United States
🇦🇹 Vienna, Austria
Travel Between:

$399

View Deal
Oct - Oct 2025
💰 $199
🇺🇸 Chicago, United States
🇮🇸 Reykjavik, Iceland
Travel Between:

$766

View Deal
Jan - Jan 2026
💰 $383
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$357

View Deal
Jan - Jan 2026
💰 $178
🇺🇸 Chicago, United States
🇺🇸 Fairbanks, United States
Travel Between:

$262

View Deal
Nov - Nov 2025
💰 $131
🇺🇸 Chicago, United States
🇩🇴 Punta Cana, Dominican Republic
Travel Between:

$659

View Deal
Nov - Nov 2025
💰 $329
🇺🇸 Chicago, United States
🇮🇳 New Delhi, India
Travel Between:

$135

View Deal
Nov - Nov 2025
💰 $67
🇺🇸 Chicago, United States
🇺🇸 San Diego, United States
Travel Between:

$423

View Deal
Nov - Nov 2025
💰 $211
🇺🇸 Chicago, United States
🇵🇪 Lima, Peru
Travel Between:

$464

View Deal
Mar - Mar 2026
💰 $232
🇺🇸 Chicago, United States
🇨🇭 Zurich, Switzerland
Travel Between:

$719

View Deal
Jan - Jan 2026
💰 $359
🇺🇸 Chicago, United States
🇻🇳 Ho Chi Minh City, Vietnam
Travel Between:

$459

View Deal
Nov - Nov 2025
💰 $229
🇺🇸 Chicago, United States
🇧🇷 Florianopolis, Brazil
Travel Between:

$749

View Deal
Jan - Jan 2026
💰 $374
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$419

View Deal
Nov - Nov 2025
💰 $209
🇺🇸 Chicago, United States
🇪🇸 Barcelona, Spain
Travel Between:

$387

View Deal
Nov - Nov 2025
💰 $193
🇺🇸 Chicago, United States
🇧🇷 Sao Paulo, Brazil
Travel Between:

$435

View Deal
Feb - Feb 2026
💰 $217
🇺🇸 Chicago, United States
🇧🇷 Sao Paulo, Brazil
Travel Between:

$196

View Deal
Jan - Jan 2026
💰 $98
🇺🇸 Chicago, United States
🇬🇹 Guatemala City, Guatemala
Travel Between:

$218

View Deal
Nov - Nov 2025
💰 $109
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between:

$163

View Deal
Jan - Jan 2026
💰 $81
🇺🇸 Chicago, United States
🇺🇸 Palm Springs, United States
Travel Between:

$361

View Deal
Nov - Nov 2025
💰 $180
🇺🇸 Chicago, United States
🇺🇸 Kahului, United States
Travel Between:

$698

View Deal
Nov - Nov 2025
💰 $349
🇺🇸 Chicago, United States
🇹🇭 Bangkok, Thailand
Travel Between:

$423

View Deal
Nov - Nov 2025
💰 $211
🇺🇸 Chicago, United States
🇪🇸 Madrid, Spain
Travel Between:

$469

View Deal
Nov - Nov 2025
💰 $234
🇺🇸 Chicago, United States
🇪🇸 Bilbao, Spain
Travel Between: