Flights from Chicago starting at USD 389

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Best Flight Deals from Chicago

USD
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Chicago (ORD)to

Lisbon (LIS)
04/02/2026 - 08/02/2026
From
USD 489
Viewed 15 hours ago
Round trip
Economy

Chicago (ORD)to

Rome (FCO)
04/03/2026 - 17/03/2026
From
USD 478
Viewed 11 hours ago
Round trip
Economy

Chicago (ORD)to

Madrid (MAD)
30/01/2026 - 05/02/2026
From
USD 431
Viewed 18 hours ago
Round trip
Economy

Chicago (ORD)to

Barcelona (BCN)
27/02/2026 - 08/03/2026
From
USD 476
Viewed 14 hours ago
Round trip
Economy

Chicago (ORD)to

Porto (OPO)
31/12/2025 - 07/01/2026
From
USD 1,006
Viewed 8 hours ago
Round trip
Economy

Chicago (ORD)to

Sevilla (SVQ)
14/01/2026 - 25/01/2026
From
USD 467
Viewed 41 minutes ago
Round trip
Economy

Chicago (ORD)to

Malaga (AGP)
11/01/2026 - 16/01/2026
From
USD 591
Viewed 13 hours ago
Round trip
Economy

Chicago (ORD)to

Casablanca (CMN)
16/01/2026 - 24/01/2026
From
USD 673
Viewed 7 hours ago
Round trip
Economy

*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

USD

Chicago (ORD)to

Lisbon (LIS)
08/03/2026 - 18/03/2026

Round trip

Business

From
USD 3,322
Viewed 15 hours ago

Chicago (ORD)to

Lisbon (LIS)
30/01/2026 - 06/02/2026

Round trip

Business

From
USD 3,322
Viewed 17 hours ago

Chicago (ORD)to

Rome (FCO)
04/03/2026 - 17/03/2026

Round trip

Business

From
USD 2,821
Viewed 11 hours ago

Chicago (ORD)to

Madrid (MAD)
18/02/2026 - 04/03/2026

Round trip

Business

From
USD 3,131
Viewed 11 hours ago

Chicago (ORD)to

Madrid (MAD)
30/01/2026 - 05/02/2026

Round trip

Business

From
USD 3,131
Viewed 18 hours ago

Chicago (ORD)to

Barcelona (BCN)
27/02/2026 - 08/03/2026

Round trip

Business

From
USD 3,084
Viewed 14 hours ago

Chicago (ORD)to

Porto (OPO)
31/12/2025 - 07/01/2026

Round trip

Business

From
USD 3,850
Viewed 8 hours ago

Chicago (ORD)to

Sevilla (SVQ)
14/01/2026 - 25/01/2026

Round trip

Business

From
USD 3,727
Viewed 41 minutes 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.

Plan early and get the best prices

USD
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Plan early and get the best prices
From
To
Fare Type
Dates
Price
Chicago (ORD)Lisbon (LIS)Round trip
|
Economy
11/02/2026 - 20/02/2026

From

USD 489

Viewed 9 hours ago

Chicago (ORD)Lisbon (LIS)Round trip
|
Economy
30/01/2026 - 06/02/2026

From

USD 489

Viewed 17 hours ago

Chicago (ORD)Rome (FCO)Round trip
|
Economy
04/03/2026 - 17/03/2026

From

USD 478

Viewed 11 hours ago

Chicago (ORD)Rome (FCO)Round trip
|
Economy
04/04/2026 - 11/04/2026

From

USD 495

Viewed 10 hours ago

Chicago (ORD)Madrid (MAD)Round trip
|
Economy
30/01/2026 - 05/02/2026

From

USD 431

Viewed 18 hours ago

Chicago (ORD)Madrid (MAD)Round trip
|
Economy
22/04/2026 - 28/04/2026

From

USD 441

Viewed 6 hours ago

Chicago (ORD)Paris (ORY)Round trip
|
Economy
03/05/2026 - 10/05/2026

From

USD 389

Viewed 6 hours ago

Chicago (ORD)Paris (ORY)Round trip
|
Economy
06/05/2026 - 20/05/2026

From

USD 389

Viewed 19 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.

Top TAP Air Portugal Routes from Chicago