Image Credits: mgkm photography, creative commons 2.0 (flickr)
Published January 22, 2026 by

Nonstop Flights: Chicago to Lisbon, Portugal $383-$399 round-trip [January-February] – Tap Air Portugal

[01/22/2026 @ 10:27 AM CT] Deal time-stamp.
[2026-01-30 07:34:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

Deals are usually valid 24 to 72 hours after posting, but can expire at any time (see time-stamp).

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Tap Air Portugal has round-trip flights from Chicago (ORD) to Lisbon (LIS) for $383-$399, NONSTOP. Flights January to February. Departures on Wednesday, Friday, and Sunday. 7-day minimum stay required.

Upgrading to a higher fare class that includes a checked bag for $65 may be cheaper than booking the “Discount” fare with the added $95 checked bag fee.

Some small OTAs on Skyscanner have this for as low as $383; which is slightly cheaper than the airline. If you plan on booking there, beware of any site that charges a fee to cancel a ticket within the 24-hour “free” period. Use unknown booking sites at your own risk.

Flights on TAP allow for a free stopover (up to 5-days) in their hub city. This will be useful if you want to spend time exploring Porto or Lisbon before heading to your final destination. Link: More details on the TAP stopover program.

You can usually save more money by booking your flight+hotel together as a package instead of separately.

We post new flight deals often! You can check out our other deals by returning to the Front Page of our website: escape.flights (linked).

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Use the example date links on our website to pull up the fare.

Lisbon fares: [2026-01-30 07:34:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

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  • Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on Expedia, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.


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Ren P. Artemio

Ren P. Artemio

Ren is the Chief Director of Nap Times at Escape Houston, Escape ATX, Cheap DFW, and Escape Flights. He really likes researching airfare and the travel industry, especially when it means getting a cheap flight to anywhere (he's not picky).

Airfare Deals Flights from Chicago / Milwaukee Lisbon TAP Air Portugal