Cheap Flights: Chicago to Milan $368-$431 r/t [Feb, Apr, May] (fare has high bag fees) – Tap Air Portugal

[11/19/2021 @ 12:09 PM CT] Book this fare on: Priceline, BookingBuddy, Travelocity, Tripadvisor, Skyscanner, Expedia, Orbitz, Hotwire, CheapTickets.
[12/1/2021 @ 02:36 PM CT] This deal is still available, but the original date ranges may have shifted. We have updated the example date links in this post to reflect those changes. Expect prices to fluctuate by about +/- 10%.

The details on this page were accurate when this post was last updated (see time-stamp). Deals are usually valid 24 to 72 hours after posting, but can expire at any time. This website contains cookies for personalized ads and links to companies that may compensate this site when you click on their link. By continuing to use this website, you consent to the use of ads, affiliate links, and cookies.

Tap Air Portugal has round-trip flights from Chicago (ORD) to Milan (MXP) for $382-$417 with a connection. Flights in February, April, and May.

Note: Some small OTAs on Skyscanner have this for about $368. 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.

Carry on bag with a maximum weight of 17.6 lbs is allowed for free on TAP. You can avoid seat selection fees by accepting the randomly assigned seat at the gate. Be advised that TAP charges about $95 each-way for a regular sized checked bag for their “Discount” fare class on their International flights to/from the USA. Upgrading to a higher fare class that includes a carry-on bag (for about $60 each-way) may be cheaper than booking the discount fare with the added carry-on bag fee.

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



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I was able to pull this up on Priceline. Screenshot taken when this post was initially created. See timestamps at the top of this post.

Note: OTAs such as Travelocity and Priceline allow free cancellation without penalty within 24-hours after you purchase. As deals sell-out or expire quickly, this policy will allow you to “lock-in” the cheap fare while you sort out a plan. Just keep in mind that after 24-hours, you will not be able to cancel without the regular penalty.

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