$394 Cheap flight deals from Chicago (CHI) to Cascais (LIS)

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This Weekend's Flight Deals from Chicago to Cascais

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, Nov 16 - Wed, Dec 3
ORD
O'Hare Intl.
LIS
Humberto Delgado
$456 Roundtrip, found 11 hours ago
$456
Roundtrip
found 11 hours ago
Select Iberia flight, departing Sun, Nov 16 from O'Hare Intl. to Humberto Delgado, returning Wed, Dec 3, priced at $456 found 11 hours ago
Sat, Nov 15 - Sat, Dec 20
MDW
Midway Intl.
LIS
Humberto Delgado
$1,145 Roundtrip, found 4 days ago
$1,145
Roundtrip
found 4 days ago
Select Virgin Atlantic flight, departing Sat, Nov 15 from Midway Intl. to Humberto Delgado, returning Sat, Dec 20, priced at $1,145 found 4 days ago

Airfares from $394 One Way, $396 Round Trip from Chicago to Cascais

Prices starting at $396 for return flights and $394 for one-way flights to Cascais 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, Feb 4 - Sun, Feb 8
ORD
Chicago
LIS
Lisbon
$396 Roundtrip, found 2 hours ago
$396
Roundtrip
found 2 hours ago
Select Icelandair flight, departing Wed, Feb 4 from Chicago to Lisbon, returning Sun, Feb 8, priced at $396 found 2 hours ago
Tue, Mar 3 - Wed, Mar 11
ORD
Chicago
LIS
Lisbon
$440 Roundtrip, found 5 days ago
$440
Roundtrip
found 5 days ago
Select Lufthansa flight, departing Tue, Mar 3 from Chicago to Lisbon, returning Wed, Mar 11, priced at $440 found 5 days ago
Wed, Jan 21 - Tue, Jan 27
ORD
Chicago
LIS
Lisbon
$444 Roundtrip, found 3 days ago
$444
Roundtrip
found 3 days ago
Select Iberia flight, departing Wed, Jan 21 from Chicago to Lisbon, returning Tue, Jan 27, priced at $444 found 3 days ago
Wed, Jan 21 - Wed, Jan 28
ORD
Chicago
LIS
Lisbon
$448 Roundtrip, found 4 days ago
$448
Roundtrip
found 4 days ago
Select British Airways flight, departing Wed, Jan 21 from Chicago to Lisbon, returning Wed, Jan 28, priced at $448 found 4 days ago
Wed, Dec 31 - Tue, Jan 13
ORD
Chicago
LIS
Lisbon
$459 Roundtrip, found 4 days ago
$459
Roundtrip
found 4 days ago
Select Aer Lingus flight, departing Wed, Dec 31 from Chicago to Lisbon, returning Tue, Jan 13, priced at $459 found 4 days ago

Cascais economy flight packages

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

Eurostars Das Letras

9/10 Wonderful! (1,005 reviews)

Dec 27 - Jan 3

7 night stay

Chicago (CHI) to Lisbon (LIS)

KLM • Non-stop • Coach

Lisbon (LIS) to Chicago (CHI)

Delta • Non-stop • Coach
Price was $3,473, price is now $2,662 per person
$2,662
per person
found 1 day ago
Not a five star. More like 3.5 stars

Reviewed on Aug 3, 2025

Eurostars Lisboa Baixa
4.0-star property

Eurostars Lisboa Baixa

9.8/10 Exceptional! (209 reviews)

Dec 27 - Jan 3

7 night stay

Chicago (CHI) to Lisbon (LIS)

KLM • Non-stop • Coach

Lisbon (LIS) to Chicago (CHI)

Delta • Non-stop • Coach
Price was $3,849, price is now $2,898 per person
$2,898
per person
found 1 day ago
Great staff and excellent location.

Reviewed on Jun 9, 2025

Aurea Museum by Eurostars Hotel Company
5.0-star property

Aurea Museum by Eurostars Hotel Company

9.4/10 Exceptional! (1,013 reviews)

Dec 27 - Jan 3

7 night stay

Chicago (CHI) to Lisbon (LIS)

KLM • Non-stop • Coach

Lisbon (LIS) to Chicago (CHI)

Delta • Non-stop • Coach
Price was $3,762, price is now $2,857 per person
$2,857
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

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More About Flying To Cascais from Chicago

Route Information for Flights from Chicago to Cascais

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

Chicago to Cascais

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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.