$352 Cheap flight deals from Chicago (CHI) to Sintra (LIS)

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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 - Sun, Feb 1
ORD
O'Hare Intl.
LIS
Humberto Delgado
$399 Roundtrip, found 6 hours ago
$399
Roundtrip
found 6 hours ago
Select TAP Portugal flight, departing Sun, Jan 25 from O'Hare Intl. to Humberto Delgado, returning Sun, Feb 1, priced at $399 found 6 hours ago

Airfares from $352 One Way, $398 Round Trip from Chicago to Sintra

Prices starting at $398 for return flights and $352 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
$398 Roundtrip, found 13 hours ago
$398
Roundtrip
found 13 hours ago
Select Icelandair flight, departing Wed, Apr 8 from Chicago to Lisbon, returning Sun, Apr 19, priced at $398 found 13 hours ago
Wed, Feb 11 - Sun, Feb 15
ORD
Chicago
LIS
Lisbon
$399 Roundtrip, found 1 hour ago
$399
Roundtrip
found 1 hour ago
Select TAP Portugal flight, departing Wed, Feb 11 from Chicago to Lisbon, returning Sun, Feb 15, priced at $399 found 1 hour ago
Mon, Feb 2 - Mon, Feb 9
ORD
Chicago
LIS
Lisbon
$448 Roundtrip, found 2 days ago
$448
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Feb 2 from Chicago to Lisbon, returning Mon, Feb 9, priced at $448 found 2 days ago
Tue, Mar 10 - Tue, Mar 17
ORD
Chicago
LIS
Lisbon
$451 Roundtrip, found 3 days ago
$451
Roundtrip
found 3 days ago
Select Iberia flight, departing Tue, Mar 10 from Chicago to Lisbon, returning Tue, Mar 17, priced at $451 found 3 days ago
Tue, Apr 14 - Wed, Apr 29
ORD
Chicago
LIS
Lisbon
$460 Roundtrip, found 1 hour ago
$460
Roundtrip
found 1 hour ago
Select British Airways flight, departing Tue, Apr 14 from Chicago to Lisbon, returning Wed, Apr 29, priced at $460 found 1 hour ago

Sintra economy flight packages

Price found within the past 48 hours. Click for updated prices.
Eurostars Universal Lisboa
5.0-star property

Eurostars Universal Lisboa

9.2/10 Wonderful! (1,092 reviews)

Mar 19 - Mar 23

4 night stay

Chicago (CHI) to Lisbon (LIS)

Lufthansa • Non-stop roundtrip • Coach
Price was $1,205, price is now $859 per person
$859
per person
found 1 day ago
Everything is excellent, room, staff, breakfast, location close to big market and walking distance restaurants. We will return

Reviewed on Dec 10, 2025

Lisbon Canaan Boutique Apartments Gaivotas
4.0-star property

Lisbon Canaan Boutique Apartments Gaivotas

8.8/10 Excellent! (71 reviews)

Feb 22 - Feb 28

6 night stay

Chicago (ORD) to Lisbon (LIS)

United • Non-stop • Coach

Lisbon (LIS) to Chicago (ORD)

Lufthansa • Non-stop • Coach
Price was $1,232, price is now $920 per person
$920
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

Pestana Palace Lisboa Hotel & National Monument - The Leading Hotels of the World
5.0-star property

Pestana Palace Lisboa Hotel & National Monument - The Leading Hotels of the World

9.2/10 Wonderful! (815 reviews)

Feb 25 - Mar 1

4 night stay

Chicago (CHI) to Lisbon (LIS)

United • Non-stop • Coach

Lisbon (LIS) to Chicago (CHI)

Lufthansa • Non-stop • Coach
Price was $1,161, price is now $892 per person
$892
per person
found 11 hours ago
Absolutely beautiful hotel! Excellent staff, lovely room, fabulous breakfasts! Enjoyed the pools and steam room. Would highly recommend!

Reviewed on Oct 16, 2023

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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

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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.