Category: <span>Milan</span>

Tap Air Portugal has round-trip flights from Chicago (ORD) to Milan (MXP) for $403 with a connection. Flights January to May.

Some small OTAs on Skyscanner have this for cheaper than the airline ($385). 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. Upgrading to a higher fare class that includes a carry-on bag for $65 may be cheaper than booking the “Discount” fare with the added $95 carry-on bag fee.

Click for more details and booking links Cheap Flights: Chicago to Milan $385-$416 r/t [January-May] – Tap Air Portugal

Airfare Deals Flights from Chicago / Milwaukee Milan TAP Air Portugal

Airfare Deals Flights from Chicago / Milwaukee Milan Star Alliance United

Tap Air Portugal has round-trip flights from Chicago (ORD) to Milan (MXP) for $384-$416 with a connection. Flights October, November, January, February, March, April, and May. 7-day minimum stay required.

This fare has a long connection in Lisbon, which makes it a good candidate for a stopover. 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.

Click for more details and booking links Cheap Flights: Chicago to Milan $384-$416 r/t (long connection in Lisbon) – Tap Air Portugal

Airfare Deals Flights from Chicago / Milwaukee Milan TAP Air Portugal

Airfare Deals Flights from Chicago / Milwaukee Milan Scandinavian Airlines

SAS has round-trip flights from Chicago (ORD) to Milan (MXP) for $450 with a connection. Flights in August, September, October, November, December, January, and February. Extended weekends available.

Carry on bag with a maximum weight of 18 lbs is allowed for free on SAS. You can avoid seat selection fees by accepting the randomly assigned seat at the gate. Upgrading to a higher fare class that includes a full-size carry-on bag for $28 may be cheaper than booking the discount fare with the added carry-on bag fee (for about $60).

Click for more details and booking links Cheap Flights: Chicago to Milan $450 r/t [Aug-Feb] – SAS

Airfare Deals Flights from Chicago / Milwaukee Milan SAS

Air France Airfare Deals Delta Flights from Denver Milan SkyTeam Star Alliance United

Airfare Deals American Airlines British Airways Delta Flights from Phoenix KLM Milan Oneworld SkyTeam

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.

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

Airfare Deals Flights from Chicago / Milwaukee Milan TAP Air Portugal

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Airfare Deals American Airlines British Airways Flights from New York Iberia JetBlue Milan Oneworld