Flights from Chicago starting at USD 429

Best Flight Deals from Chicago

USD
Select travel class

Chicago (ORD)to

Madrid (MAD)
12/02/2025 - 19/02/2025
From
USD 500*
Viewed 5 hours ago
Round-trip
|
Economy

Chicago (ORD)to

Porto (OPO)
05/03/2025 - 19/03/2025
From
USD 499*
Viewed 7 hours ago
Round-trip
|
Economy

Chicago (ORD)to

London (LHR)
16/02/2025 - 27/02/2025
From
USD 588*
Viewed 17 hours ago
Round-trip
|
Economy

Chicago (ORD)to

Milan (MXP)
16/02/2025 - 23/02/2025
From
USD 580*
Viewed 4 hours ago
Round-trip
|
Economy

Chicago (ORD)to

Sevilla (SVQ)
19/01/2025 - 02/02/2025
From
USD 498*
Viewed 13 hours ago
Round-trip
|
Economy

Chicago (ORD)to

Casablanca (CMN)
02/02/2025 - 03/04/2025
From
USD 832*
Viewed 2 hours ago
Round-trip
|
Economy

Chicago (ORD)to

Malaga (AGP)
14/03/2025 - 24/03/2025
From
USD 1,290*
Viewed 9 hours ago
Round-trip
|
Economy

Chicago (ORD)to

Funchal (FNC)
07/02/2025 - 15/02/2025
From
USD 752*
Viewed 13 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

Madrid (MAD)
19/02/2025 - 23/02/2025

Round-trip

|

Business

From
USD 2,999*
Viewed 12 hours ago
Chicago (ORD) to Madrid (MAD) 19/02/2025 - 23/02/2025 Round-trip Business From USD 2,999 Viewed 12 hours ago

Chicago (ORD)to

Madrid (MAD)
12/02/2025 - 19/02/2025

Round-trip

|

Business

From
USD 2,999*
Viewed 5 hours ago
Chicago (ORD) to Madrid (MAD) 12/02/2025 - 19/02/2025 Round-trip Business From USD 2,999 Viewed 5 hours ago

Chicago (ORD)to

Porto (OPO)
22/01/2025 - 31/01/2025

Round-trip

|

Business

From
USD 2,899*
Viewed 1 hour ago
Chicago (ORD) to Porto (OPO) 22/01/2025 - 31/01/2025 Round-trip Business From USD 2,899 Viewed 1 hour ago

Chicago (ORD)to

Porto (OPO)
09/02/2025 - 15/02/2025

Round-trip

|

Business

From
USD 2,899*
Viewed 14 hours ago
Chicago (ORD) to Porto (OPO) 09/02/2025 - 15/02/2025 Round-trip Business From USD 2,899 Viewed 14 hours ago

Chicago (ORD)to

London (LHR)
16/02/2025 - 27/02/2025

Round-trip

|

Business

From
USD 2,797*
Viewed 17 hours ago
Chicago (ORD) to London (LHR) 16/02/2025 - 27/02/2025 Round-trip Business From USD 2,797 Viewed 17 hours ago

Chicago (ORD)to

London (LHR)
11/04/2025 - 20/04/2025

Round-trip

|

Business

From
USD 3,702*
Viewed 10 hours ago
Chicago (ORD) to London (LHR) 11/04/2025 - 20/04/2025 Round-trip Business From USD 3,702 Viewed 10 hours ago

Chicago (ORD)to

Milan (MXP)
16/02/2025 - 23/02/2025

Round-trip

|

Business

From
USD 2,899*
Viewed 4 hours ago
Chicago (ORD) to Milan (MXP) 16/02/2025 - 23/02/2025 Round-trip Business From USD 2,899 Viewed 4 hours ago

Chicago (ORD)to

Milan (MXP)
12/03/2025 - 21/03/2025

Round-trip

|

Business

From
USD 2,899*
Viewed 8 hours ago
Chicago (ORD) to Milan (MXP) 12/03/2025 - 21/03/2025 Round-trip Business From USD 2,899 Viewed 8 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.

Plan early and get the best prices

USD
Cash
Plan early and get the best prices
From
To
Fare Type
Dates
Price
FromChicago (ORD)ToMadrid (MAD)Round-trip
|
Economy
12/02/2025 - 19/02/2025

From

USD 500*

Viewed 5 hours ago

From Chicago To Madrid Fare Type Round-trip Economy Dates 12/02/2025 - 19/02/2025 From USD 500 Viewed 5 hours ago
FromChicago (ORD)ToMadrid (MAD)Round-trip
|
Economy
09/03/2025 - 25/04/2025

From

USD 509*

Viewed 8 hours ago

From Chicago To Madrid Fare Type Round-trip Economy Dates 09/03/2025 - 25/04/2025 From USD 509 Viewed 8 hours ago
FromChicago (ORD)ToPorto (OPO)Round-trip
|
Economy
05/03/2025 - 19/03/2025

From

USD 499*

Viewed 7 hours ago

From Chicago To Porto Fare Type Round-trip Economy Dates 05/03/2025 - 19/03/2025 From USD 499 Viewed 7 hours ago
FromChicago (ORD)ToPorto (OPO)Round-trip
|
Economy
26/04/2025 - 09/05/2025

From

USD 569*

Viewed 11 hours ago

From Chicago To Porto Fare Type Round-trip Economy Dates 26/04/2025 - 09/05/2025 From USD 569 Viewed 11 hours ago
FromChicago (ORD)ToLondon (LHR)Round-trip
|
Economy
16/02/2025 - 27/02/2025

From

USD 588*

Viewed 17 hours ago

From Chicago To London Fare Type Round-trip Economy Dates 16/02/2025 - 27/02/2025 From USD 588 Viewed 17 hours ago
FromChicago (ORD)ToLondon (LHR)Round-trip
|
Economy
30/04/2025 - 13/05/2025

From

USD 595*

Viewed 10 hours ago

From Chicago To London Fare Type Round-trip Economy Dates 30/04/2025 - 13/05/2025 From USD 595 Viewed 10 hours ago
FromChicago (ORD)ToMilan (MXP)Round-trip
|
Economy
16/02/2025 - 23/02/2025

From

USD 580*

Viewed 4 hours ago

From Chicago To Milan Fare Type Round-trip Economy Dates 16/02/2025 - 23/02/2025 From USD 580 Viewed 4 hours ago
FromChicago (ORD)ToMilan (MXP)Round-trip
|
Economy
10/03/2025 - 20/03/2025

From

USD 809*

Viewed 8 hours ago

From Chicago To Milan Fare Type Round-trip Economy Dates 10/03/2025 - 20/03/2025 From USD 809 Viewed 8 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.