$327 Cheap flight deals from Chicago (CHI) to Serra da Estrela (OPO)

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This Weekend's Flight Deals from Chicago to Serra da Estrela

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, Oct 25 - Tue, Nov 3
ORD
O'Hare Intl.
OPO
Dr. Francisco de Sa Carneiro
$684 Roundtrip, found 1 day ago
$684
Roundtrip
found 1 day ago
Select TAP Portugal flight, departing Sun, Oct 25 from O'Hare Intl. to Dr. Francisco de Sa Carneiro, returning Tue, Nov 3, priced at $684 found 1 day ago
Fri, Oct 23 - Fri, Oct 30
ORD
O'Hare Intl.
LIS
Humberto Delgado
$1,027 Roundtrip, just found
$1,027
Roundtrip
just found
Select TAP Portugal flight, departing Fri, Oct 23 from O'Hare Intl. to Humberto Delgado, returning Fri, Oct 30, priced at $1,027 just found
Fri, Oct 23 - Mon, Oct 26
MDW
Midway Intl.
LIS
Humberto Delgado
$1,793 Roundtrip, found 3 hours ago
$1,793
Roundtrip
found 3 hours ago
Select Delta flight, departing Fri, Oct 23 from Midway Intl. to Humberto Delgado, returning Mon, Oct 26, priced at $1,793 found 3 hours ago

Airfares from $327 One Way, $582 Round Trip from Chicago to Serra da Estrela

Prices starting at $582 for return flights and $327 for one-way flights to Serra da Estrela 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, Nov 4 - Wed, Nov 11
ORD
Chicago
OPO
Porto
$582 Roundtrip, found 19 hours ago
$582
Roundtrip
found 19 hours ago
Select TAP Portugal flight, departing Wed, Nov 4 from Chicago to Porto, returning Wed, Nov 11, priced at $582 found 19 hours ago
Thu, Dec 31 - Wed, Jan 6
ORD
Chicago
LIS
Lisbon
$652 Roundtrip, found 6 days ago
$652
Roundtrip
found 6 days ago
Select Scandinavian Airlines flight, departing Thu, Dec 31 from Chicago to Lisbon, returning Wed, Jan 6, priced at $652 found 6 days ago
Mon, Nov 30 - Tue, Dec 8
ORD
Chicago
LIS
Lisbon
$658 Roundtrip, found 3 days ago
$658
Roundtrip
found 3 days ago
Select Icelandair flight, departing Mon, Nov 30 from Chicago to Lisbon, returning Tue, Dec 8, priced at $658 found 3 days ago
Wed, Nov 4 - Wed, Nov 11
ORD
Chicago
LIS
Lisbon
$689 Roundtrip, just found
$689
Roundtrip
just found
Select TAP Portugal flight, departing Wed, Nov 4 from Chicago to Lisbon, returning Wed, Nov 11, priced at $689 just found
Wed, Dec 2 - Fri, Dec 11
ORD
Chicago
LIS
Lisbon
$712 Roundtrip, found 3 hours ago
$712
Roundtrip
found 3 hours ago
Select United flight, departing Wed, Dec 2 from Chicago to Lisbon, returning Fri, Dec 11, priced at $712 found 3 hours ago

Serra da Estrela economy flight packages

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

Eurostars Lisboa Baixa

9.8/10 Exceptional! (352 reviews)

Dec 5 - Dec 10

5 night stay

Chicago (CHI) to Lisbon (LIS)

TAP Portugal • Coach

Lisbon (LIS) to Chicago (CHI)

Aer Lingus • Coach
Price was $1,619, price is now $1,208 per person
$1,208
per person
found 1 day ago
Very helpful staff and front desk. Would walk you to show you directions. The room was large and modern and location cannot be beaten if you love to be in the middle of the action. Would come back thanks.

Reviewed on Oct 16, 2026

Pousada de Lisboa - Small Luxury Hotels Of The World
5.0-star property

Pousada de Lisboa - Small Luxury Hotels Of The World

9.6/10 Exceptional! (674 reviews)

Dec 5 - Dec 10

5 night stay

Chicago (CHI) to Lisbon (LIS)

TAP Portugal • Coach

Lisbon (LIS) to Chicago (CHI)

Aer Lingus • Coach
Price was $1,938, price is now $1,449 per person
$1,449
per person
found 1 day ago
This is a great hotel in a great location. Close to dining, shopping and the train station for day trips! I will definitely stay here again!

Reviewed on Oct 12, 2026

138 Liberdade Hotel
5.0-star property

138 Liberdade Hotel

9.6/10 Exceptional! (870 reviews)

Dec 5 - Dec 10

5 night stay

Chicago (CHI) to Lisbon (LIS)

TAP Portugal • Coach

Lisbon (LIS) to Chicago (CHI)

Aer Lingus • Coach
Price was $1,760, price is now $1,318 per person
$1,318
per person
found 1 day ago
The hotel is in a great location allowing one to walk to shopping and restaurants and is situated on one of Lisbon’s less steep streets. The ambiance of the hotel is lovely reminding me of an art deco style. The staff were cordial and so welcoming. The room I booked was spacious and well appointed. I also included the breakfast package with my booking and would definitely recommend as the food was fresh and included ample selections. I so enjoyed visiting Portugal and the 138 Liberdade Hotel amplified why my visit was so wonderful.

Reviewed on Oct 17, 2026

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More About Flying To Serra da Estrela from Chicago

Route Information for Flights from Chicago to Serra da Estrela

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

Chicago to Serra da Estrela

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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.