$352 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.

Sat, Jul 25 - Sun, Aug 2
ORD
O'Hare Intl.
LIS
Humberto Delgado
$1,085 Roundtrip, found 9 hours ago
$1,085
Roundtrip
found 9 hours ago
Select Icelandair flight, departing Sat, Jul 25 from O'Hare Intl. to Humberto Delgado, returning Sun, Aug 2, priced at $1,085 found 9 hours ago
Sat, Jul 25 - Sat, Aug 1
MDW
Midway Intl.
LIS
Humberto Delgado
$1,405 Roundtrip, found 6 days ago
$1,405
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Jul 25 from Midway Intl. to Humberto Delgado, returning Sat, Aug 1, priced at $1,405 found 6 days ago

Airfares from $352 One Way, $471 Round Trip from Chicago to Cascais

Prices starting at $471 for return flights and $352 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.

Sat, Oct 3 - Sun, Oct 18
ORD
Chicago
LIS
Lisbon
$471 Roundtrip, found 4 days ago
$471
Roundtrip
found 4 days ago
Select Icelandair flight, departing Sat, Oct 3 from Chicago to Lisbon, returning Sun, Oct 18, priced at $471 found 4 days ago
Fri, Oct 9 - Fri, Oct 23
ORD
Chicago
LIS
Lisbon
$648 Roundtrip, just found
$648
Roundtrip
just found
Select TAP Portugal flight, departing Fri, Oct 9 from Chicago to Lisbon, returning Fri, Oct 23, priced at $648 just found
Mon, Oct 19 - Tue, Nov 3
ORD
Chicago
LIS
Lisbon
$718 Roundtrip, found 5 days ago
$718
Roundtrip
found 5 days ago
Select Air Canada flight, departing Mon, Oct 19 from Chicago to Lisbon, returning Tue, Nov 3, priced at $718 found 5 days ago
Sun, Nov 1 - Wed, Nov 18
ORD
Chicago
LIS
Lisbon
$726 Roundtrip, found 4 days ago
$726
Roundtrip
found 4 days ago
Select Lufthansa flight, departing Sun, Nov 1 from Chicago to Lisbon, returning Wed, Nov 18, priced at $726 found 4 days ago
Mon, Nov 2 - Wed, Nov 11
ORD
Chicago
LIS
Lisbon
$729 Roundtrip, found 17 hours ago
$729
Roundtrip
found 17 hours ago
Select Iberia flight, departing Mon, Nov 2 from Chicago to Lisbon, returning Wed, Nov 11, priced at $729 found 17 hours ago

Cascais economy flight packages

Price found within the past 48 hours. Click for updated prices.
EPIC SANA Marques Hotel
5.0-star property

EPIC SANA Marques Hotel

9.6/10 Exceptional! (1,419 reviews)

Sep 6 - Sep 11

5 night stay

Chicago (CHI) to Lisbon (LIS)

TAP Portugal • Roundtrip • Coach
Price was $1,896, price is now $1,546 per person
$1,546
per person
found 8 hours ago
No faults amazing place

Reviewed on Jul 19, 2026

Eurostars Universal Lisboa
5.0-star property

Eurostars Universal Lisboa

9.2/10 Wonderful! (1,303 reviews)

Sep 12 - Sep 15

3 night stay

Chicago (CHI) to Lisbon (LIS)

American Airlines • Non-stop roundtrip • Coach
Price was $2,030, price is now $1,630 per person
$1,630
per person
found 1 day ago
breakfast very basic, very slow drinks service Waited 25 mins for coffee and in the end collected it myslef !

Reviewed on Jul 20, 2026

Hotel Hotel Avenida da Liberdade, a Member of Design Hotel
4.0-star property

Hotel Hotel Avenida da Liberdade, a Member of Design Hotel

9.8/10 Exceptional! (362 reviews)

Aug 27 - Sep 2

6 night stay

Chicago (ORD) to Lisbon (LIS)

TAP Portugal • Roundtrip • Coach
Price was $2,065, price is now $1,660 per person
$1,660
per person
found 19 hours ago
Everything about our stay was excellent Great location, lovely staff, fabulous food and very comfortable. Would highly recommend.

Reviewed on Jul 9, 2026

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Cascais packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
AlmaLusa Alfama
4.0-star property

AlmaLusa Alfama

9.8/10 Exceptional! (207 reviews)

Sep 16 - Sep 19

3 night stay

Chicago (ORD) to Lisbon (LIS)

SAS • Non-stop roundtrip • PremiumEconomy
Price was $2,361, price is now $2,051 per person
$2,051
per person
found 1 day ago
Great location, staff, rooms

Reviewed on Jul 17, 2026

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

9.4/10 Exceptional! (909 reviews)

Sep 16 - Sep 19

3 night stay

Chicago (ORD) to Lisbon (LIS)

SAS • Non-stop roundtrip • PremiumEconomy
Price was $2,654, price is now $2,161 per person
$2,161
per person
found 1 day ago
Everything

Reviewed on Jul 18, 2026

MACAM Hotel
5.0-star property

MACAM Hotel

9.8/10 Exceptional! (58 reviews)

Sep 16 - Sep 19

3 night stay

Chicago (ORD) to Lisbon (LIS)

SAS • Non-stop roundtrip • PremiumEconomy
Price was $2,413, price is now $2,112 per person
$2,112
per person
found 1 day ago
Very unique place!

Reviewed on Jul 12, 2026

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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.