$334 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, Oct 11 - Sat, Oct 17
ORD
O'Hare Intl.
LIS
Humberto Delgado
$1,119 Roundtrip, just found
$1,119
Roundtrip
just found
Select Air Canada flight, departing Sun, Oct 11 from O'Hare Intl. to Humberto Delgado, returning Sat, Oct 17, priced at $1,119 just found

Airfares from $334 One Way, $689 Round Trip from Chicago to Cascais

Prices starting at $689 for return flights and $334 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, Nov 18 - Wed, Nov 25
ORD
Chicago
LIS
Lisbon
$689 Roundtrip, just found
$689
Roundtrip
just found
Select TAP Portugal flight, departing Wed, Nov 18 from Chicago to Lisbon, returning Wed, Nov 25, priced at $689 just found
Sat, Dec 5 - Tue, Dec 15
ORD
Chicago
LIS
Lisbon
$712 Roundtrip, found 6 days ago
$712
Roundtrip
found 6 days ago
Select Icelandair flight, departing Sat, Dec 5 from Chicago to Lisbon, returning Tue, Dec 15, priced at $712 found 6 days ago
Tue, Nov 17 - Wed, Nov 25
ORD
Chicago
LIS
Lisbon
$726 Roundtrip, found 5 hours ago
$726
Roundtrip
found 5 hours ago
Select Scandinavian Airlines flight, departing Tue, Nov 17 from Chicago to Lisbon, returning Wed, Nov 25, priced at $726 found 5 hours ago
Wed, Mar 17 - Wed, Mar 31
ORD
Chicago
LIS
Lisbon
$730 Roundtrip, found 2 days ago
$730
Roundtrip
found 2 days ago
Select United flight, departing Wed, Mar 17 from Chicago to Lisbon, returning Wed, Mar 31, priced at $730 found 2 days ago
Tue, Jan 19 - Thu, Jan 28
ORD
Chicago
LIS
Lisbon
$731 Roundtrip, found 12 hours ago
$731
Roundtrip
found 12 hours ago
Select Finnair flight, departing Tue, Jan 19 from Chicago to Lisbon, returning Thu, Jan 28, priced at $731 found 12 hours ago

Cascais economy flight packages

Price found within the past 48 hours. Click for updated prices.
Masa Hotel 5 de Outubro
3.0-star property

Masa Hotel 5 de Outubro

8.8/10 Excellent! (198 reviews)

Nov 11 - Nov 18

7 night stay

Chicago (ORD) to Lisbon (LIS)

American Airlines • Non-stop roundtrip • Coach
Price was $1,613, price is now $1,180 per person
$1,180
per person
found 22 hours ago
Comfortable bed, air conditioner turned off and it was a bit of a challenge to get it working again. Good for one night before flight the next day.

Reviewed on Oct 1, 2026

138 Liberdade Hotel
5.0-star property

138 Liberdade Hotel

9.6/10 Exceptional! (870 reviews)

Nov 14 - Nov 20

6 night stay

Chicago (CHI) to Lisbon (LIS)

TAP Portugal • Roundtrip • Coach
Price was $1,734, price is now $1,202 per person
$1,202
per person
found 1 day ago
Bed

Reviewed on Oct 5, 2026

The Emerald House Lisbon, Curio Collection By Hilton
4.0-star property

The Emerald House Lisbon, Curio Collection By Hilton

9.6/10 Exceptional! (605 reviews)

Nov 8 - Nov 14

6 night stay

Chicago (ORD) to Lisbon (LIS)

British Airways • Non-stop • Coach

Lisbon (LIS) to Chicago (ORD)

Iberia • Non-stop • Coach
Price was $1,976, price is now $1,370 per person
$1,370
per person
found 1 day ago

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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.