Flights from Chicago starting at USD 399
Best Flight Deals from Chicago
Chicago (ORD)to
Lisbon (LIS)
Chicago (ORD)to
Madrid (MAD)
Chicago (ORD)to
Barcelona (BCN)
Chicago (ORD)to
Funchal (FNC)
Chicago (ORD)to
Rome (FCO)
Chicago (ORD)to
Porto (OPO)
Chicago (ORD)to
Sevilla (SVQ)
Chicago (ORD)to
Paris (ORY)*The fares shown have been updated in the last 48 hours and may no longer be available at the time of booking. Additional fees and charges may apply for optional products and services.
Business Flights Deals
Chicago (ORD)to
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Chicago (ORD)to
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Chicago (ORD)to
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Chicago (ORD)to
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Chicago (ORD)to
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Chicago (ORD)to
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Chicago (ORD)to
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Chicago (ORD)to
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*The fares shown have been updated in the last 48 hours and may no longer be available at the time of booking. Additional fees and charges may apply for optional products and services.
Plan early and get the best prices
From | To | Fare Type | Dates | Price | |
|---|---|---|---|---|---|
| Chicago (ORD) | Lisbon (LIS) | Round trip | Economy | 15/02/2026 - 01/03/2026 | From USD 499 Viewed 15 hours ago | |
| Chicago (ORD) | Lisbon (LIS) | Round trip | Economy | 11/02/2026 - 01/03/2026 | From USD 499 Viewed 9 hours ago | |
| Chicago (ORD) | Madrid (MAD) | Round trip | Economy | 15/04/2026 - 22/04/2026 | From USD 399 Viewed 17 hours ago | |
| Chicago (ORD) | Madrid (MAD) | Round trip | Economy | 04/02/2026 - 11/02/2026 | From USD 399 Viewed 19 hours ago | |
| Chicago (ORD) | Barcelona (BCN) | Round trip | Economy | 20/02/2026 - 27/02/2026 | From USD 419 Viewed 1 hour ago | |
| Chicago (ORD) | Barcelona (BCN) | Round trip | Economy | 18/04/2026 - 25/04/2026 | From USD 419 Viewed 2 hours ago | |
| Chicago (ORD) | Funchal (FNC) | Round trip | Economy | 11/02/2026 - 18/02/2026 | From USD 549 Viewed 19 hours ago | |
| Chicago (ORD) | Funchal (FNC) | Round trip | Economy | 22/04/2026 - 29/04/2026 | From USD 549 Viewed 20 hours ago |
*The fares shown have been updated in the last 48 hours and may no longer be available at the time of booking. Additional fees and charges may apply for optional products and services.
Travelling from Chicago
Flying from Chicago is easier and more affordable thanks to TAP Airlines. Use our website for a simple booking experience, and our Mobile Check-in allows you to check in to your flight up to 36 hours before boarding.
Flying from Chicago
Depart from O’Hare International Airport (ORD), one of the largest and busiest airports in the world. Take advantage of the wide array of shopping and dining. The airport also offers Wi-Fi, and relaxing spas and lounges.
Reaching the airport
O’Hare is located 30 km northwest of downtown Chicago. Despite the distance, the airport is easily accessible by public transportation, like the CTA Blue Line. For more convenience, hire a taxi or airport shuttle, though beware of traffic. However you arrive, book your flight from Chicago with TAP Air Portugal today, and fly in comfort and style.