$355 Cheap flight deals from Chicago (CHI) to Sintra (LIS)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Chicago to Sintra

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Jan 25 - Tue, Feb 10
ORD
O'Hare Intl.
LIS
Humberto Delgado
$454 Roundtrip, found 2 hours ago
$454
Roundtrip
found 2 hours ago
Select Iberia flight, departing Sun, Jan 25 from O'Hare Intl. to Humberto Delgado, returning Tue, Feb 10, priced at $454 found 2 hours ago

Airfares from $355 One Way, $397 Round Trip from Chicago to Sintra

Prices starting at $397 for return flights and $355 for one-way flights to Sintra were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Apr 8 - Sun, Apr 19
ORD
Chicago
LIS
Lisbon
$397 Roundtrip, found 1 hour ago
$397
Roundtrip
found 1 hour ago
Select Icelandair flight, departing Wed, Apr 8 from Chicago to Lisbon, returning Sun, Apr 19, priced at $397 found 1 hour ago
Tue, Feb 17 - Mon, Feb 23
ORD
Chicago
LIS
Lisbon
$448 Roundtrip, found 1 day ago
$448
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Feb 17 from Chicago to Lisbon, returning Mon, Feb 23, priced at $448 found 1 day ago
Tue, Mar 10 - Tue, Mar 17
ORD
Chicago
LIS
Lisbon
$451 Roundtrip, found 5 hours ago
$451
Roundtrip
found 5 hours ago
Select Iberia flight, departing Tue, Mar 10 from Chicago to Lisbon, returning Tue, Mar 17, priced at $451 found 5 hours ago
Tue, Mar 3 - Wed, Mar 11
ORD
Chicago
LIS
Lisbon
$457 Roundtrip, found 2 days ago
$457
Roundtrip
found 2 days ago
Select Virgin Atlantic flight, departing Tue, Mar 3 from Chicago to Lisbon, returning Wed, Mar 11, priced at $457 found 2 days ago
Mon, Feb 9 - Tue, Feb 17
ORD
Chicago
LIS
Lisbon
$459 Roundtrip, found 2 days ago
$459
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Feb 9 from Chicago to Lisbon, returning Tue, Feb 17, priced at $459 found 2 days ago

Sintra economy flight packages

Price found within the past 48 hours. Click for updated prices.
Inspira Liberdade Boutique Hotel
4.0-star property

Inspira Liberdade Boutique Hotel

9.2/10 Wonderful! (892 reviews)

Feb 20 - Feb 24

4 night stay

Chicago (CHI) to Lisbon (LIS)

American Airlines • Non-stop roundtrip • Coach
Price was $1,107, price is now $785 per person
$785
per person
found 1 day ago
This hotel was a wonderful balance between affordability, location, and quality accommodations. The breakfast buffet was delicious!

Reviewed on Feb 25, 2025

Lisbon Canaan Boutique Apartments Gaivotas
4.0-star property

Lisbon Canaan Boutique Apartments Gaivotas

8.8/10 Excellent! (71 reviews)

Feb 23 - Mar 1

6 night stay

Chicago (ORD) to Lisbon (LIS)

Air Canada • Non-stop • Coach

Lisbon (LIS) to Chicago (ORD)

Lufthansa • Non-stop • Coach
Price was $1,206, price is now $885 per person
$885
per person
found 1 day ago
Our family was pleasantly surprised with the space and comfort in our R. Gaivotas apartment. Bedrooms were large and welcoming, as was the sitting room with TV and dining. The surrounding area was mostly quiet (as long as the windows were shut) and just a 10-15 minute walk (albeit uphill) to the bustling hub of the city. Tram 28 stops just around the corner, and there were plenty of shops and restaurants nearby. We had a few minor plumbing issues (hot water heater had to be reset, drains were slow, fixtures a bit loose) but all were manageable and honestly to be expected in older European properties. A/C worked very well, and the washing/drying machine was very useful! Bring your own toiletries- only bar soap provided. Host was kind and responsive with clear instuctions. We would stay again!

Reviewed on Sep 8, 2022

Pousada de Lisboa, Praça do Comércio - Small Luxury Hotel
5.0-star property

Pousada de Lisboa, Praça do Comércio - Small Luxury Hotel

9.6/10 Exceptional! (614 reviews)

Feb 23 - Mar 1

6 night stay

Chicago (ORD) to Lisbon (LIS)

Air Canada • Non-stop • Coach

Lisbon (LIS) to Chicago (ORD)

Lufthansa • Non-stop • Coach
Price was $1,622, price is now $1,193 per person
$1,193
per person
found 1 day ago
It was the BEST place to stay. We enjoyed luxury, atmosphere, customer service and quiet when it was time for bed. The breakfast was perfect and location great! We will be back to Lisbon soon and we will be sure to book early so we can stay here again.

Reviewed on Sep 23, 2025

Don't see what you're looking for?
See all available trips from Chicago to Sintra
View all trips

Sintra first class flight packages

Price found within the past 48 hours. Click for updated prices.
Inspira Liberdade Boutique Hotel
4.0-star property

Inspira Liberdade Boutique Hotel

9.2/10 Wonderful! (892 reviews)

Feb 22 - Feb 28

6 night stay

Chicago (ORD) to Lisbon (LIS)

Delta • Non-stop • FirstClass

Lisbon (LIS) to Chicago (ORD)

Virgin Atlantic • Non-stop • FirstClass
Price was $4,381, price is now $3,901 per person
$3,901
per person
found 1 day ago
This hotel was a wonderful balance between affordability, location, and quality accommodations. The breakfast buffet was delicious!

Reviewed on Feb 25, 2025

Pousada de Lisboa, Praça do Comércio - Small Luxury Hotel
5.0-star property

Pousada de Lisboa, Praça do Comércio - Small Luxury Hotel

9.6/10 Exceptional! (614 reviews)

Feb 22 - Feb 28

6 night stay

Chicago (ORD) to Lisbon (LIS)

Delta • Non-stop • FirstClass

Lisbon (LIS) to Chicago (ORD)

Virgin Atlantic • Non-stop • FirstClass
Price was $4,661, price is now $4,118 per person
$4,118
per person
found 1 day ago
It was the BEST place to stay. We enjoyed luxury, atmosphere, customer service and quiet when it was time for bed. The breakfast was perfect and location great! We will be back to Lisbon soon and we will be sure to book early so we can stay here again.

Reviewed on Sep 23, 2025

Aurea Museum by Eurostars Hotel Company
5.0-star property

Aurea Museum by Eurostars Hotel Company

9.4/10 Exceptional! (1,002 reviews)

Feb 22 - Feb 28

6 night stay

Chicago (ORD) to Lisbon (LIS)

Delta • Non-stop • FirstClass

Lisbon (LIS) to Chicago (ORD)

Virgin Atlantic • Non-stop • FirstClass
Price was $4,476, price is now $3,975 per person
$3,975
per person
found 1 day ago
Fabulous hotel in a truly historic hotel! First though, I would like to mention the amazing staff at Check in.. very pleasant, informative, and welcoming. The hotel has ancient Roman ruins underneath that have been meticulously excavated. The hotel offers private tour every day at 10am for its guests. This is a great location walkable to everything, yet slightly removed from the hustle & bustle.

Reviewed on Sep 12, 2025

Don't see what you're looking for?
See all available trips from Chicago to Sintra
View all trips

More About Flying To Sintra from Chicago

Route Information for Flights from Chicago to Sintra

Origin Airport IATA Code
CHI
Destination Airport IATA Code
LIS
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Sintra

When you’re ready to take your next trip, get the most affordable prices on flights from Chicago to Sintra with Orbitz! The guaranteed low prices and cutting-edge mobile tools on Orbits make it easy for you to plan your next great vacation.

Keep Up With Sudden Flight Changes

As any traveler knows, air travel can suddenly be temporarily halted due to service disruptions. Along with offering the best fares for flights from Chicago to Sintra, Orbitz also offers free mobile phone and email alerts that help you keep up with sudden changes to your flight plans. Choose from email, text, or voice message alerts.

Get Great Prices for Chicago to Sintra Flights

Orbitz features both an Android app and an iPhone app to give you the lowest prices for Chicago to Sintra flights. Use these mobile apps to get updates on your flight, the details of your itinerary, and to learn about available hotel deals in the area.

Fly for Less and Earn Miles

Did you know you can earn miles and points for your frequent flyer program with Orbitz? To do this with specific flights from Chicago to Sintra, enter your frequent flyer account number when you book your ticket online. For even more convenience, keep a record of your loyalty travel program numbers directly with Orbitz by storing them in your account profile. This way, you can add your account numbers to your next reservation for Chicago to Sintra flights automatically without the annoying hassle of having to look them up.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.