TAP Air Portugal is doing return flights to Chicago for £479 per person. Departures run September through March, so you've got proper winter flexibility.
The deal
Return flights to Chicago with TAP Air Portugal from £479 per person. Travel window: September to March. Flights only — you'll sort your own accommodation.
Why we like it
Chicago's a proper destination: deep-dish pizza, the architecture, that lake. £479 return is sensible money for a transatlantic flight, especially if you're flexible on dates within that six-month window.
TAP's a solid mid-range carrier, so you won't be wedged into a tin can with zero legroom — though don't expect business-class treatment at this price. You'll likely connect through Lisbon, which adds a bit of time but keeps costs down.
The catch: TAP's baggage policy is tight on economy fares, so budget for a checked bag if you need one. Read the fine print on seat selection and carry-on limits before you book.
How to book
Head to Jack's Flight Club, where this deal was spotted. They've done the legwork finding the price; you'll book direct with TAP. Check your exact travel dates against the September–March window and compare a few departure dates to lock in the best option.
📍 Explore Chicago
Use the map to scope out neighbourhoods, transport links and walking distance to the highlights.
🎟️ Top things to do in Chicago
Skip the queues with pre-booked tickets. Compare prices across GetYourGuide and Tiqets — both offer free cancellation up to 24 hours before.
#ad — we earn a small commission at no cost to you when you book through our links.
