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:

$387 to 🇧🇷 Sao Paulo, Brazil $435 to 🇧🇷 Sao Paulo, Brazil $196 to 🇬🇹 Guatemala City, Guatemala 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

$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:

$437

View Deal
Jan - Jan 2026
💰 $218
🇺🇸 Chicago, United States
🇧🇷 Sao Paulo, Brazil
Travel Between:

$443

View Deal
Nov - Nov 2025
💰 $221
🇺🇸 Chicago, United States
🇵🇹 Porto, Portugal
Travel Between:

$447

View Deal
Nov - Nov 2025
💰 $223
🇺🇸 Chicago, United States
🇮🇪 Dublin, Ireland
Travel Between:

$665

View Deal
Nov - Nov 2025
💰 $332
🇺🇸 Chicago, United States
🇦🇪 Dubai, United Arab Emirates
Travel Between:

$403

View Deal
Nov - Nov 2025
💰 $201
🇺🇸 Chicago, United States
🇧🇷 Rio De Janeiro, Brazil
Travel Between:

$291

View Deal
Nov - Nov 2025
💰 $145
🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia
Travel Between:

$374

View Deal
Mar - Mar 2026
💰 $187
🇺🇸 Chicago, United States
🇸🇪 Gothenburg, Sweden
Travel Between:

$739

View Deal
Sep - Sep 2025
💰 $369
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$349

View Deal
Oct - Oct 2025
💰 $174
🇺🇸 Chicago, United States
🇮🇸 Reykjavik, Iceland
Travel Between:

$552

View Deal
Nov - Nov 2025
💰 $276
🇺🇸 Chicago, United States
🇧🇷 Rio De Janeiro, Brazil
Travel Between:

$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: