Category: <span>Flights from Chicago / Milwaukee</span>

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Airfare Deals American Airlines Flights from Chicago / Milwaukee Key West Oneworld

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 American Airlines Flights from Chicago / Milwaukee Kahului Oneworld

Airfare Deals Flights from Chicago / Milwaukee

Airfare Deals Flights from Chicago / Milwaukee Philadelphia Star Alliance United

Airfare Deals British Airways Finnair Flights from Chicago / Milwaukee Iberia Madrid Oneworld

United, American Airlines, Iberia, British Airways and various other airlines have round-trip flights from Chicago (ORD) to Dublin (DUB) for $490, NONSTOP. Flights August, September, October, and March. No Saturday departures. Very few extended weekends available.

A Carry-on bag and also a personal item is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Click for more details and booking links Nonstop Flights: Chicago to Dublin $490 r/t [Aug-Oct, Mar] – United / American Airlines / Iberia / British Airways

Airfare Deals American Airlines British Airways Dublin Flights from Chicago / Milwaukee Iberia Oneworld Star Alliance United

American Airlines has round-trip flights from Chicago (ORD) to Sydney, Australia or Auckland (SYD, AKL) for $815-$892 with a connection. Flights in November. Departures on Thursday, Friday, and Saturday. Very few extended weekends available.

Priceline has “Express Deals” for $778-$840. With “Express Deals” the airline and exact flight are hidden until after purchase and those purchases are final. There is no 24-hour free cancellation for “Express Deals”. The flight is guaranteed to be on a major airline. Be sure to select the deal with 0 to 1 stops and a layover less than 4-hours.

A Carry-on bag, checked bag, and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Click for more details and booking links Cheap Flights: Chicago to (Sydney, Australia $778-$815) or (Auckland $840-$892) r/t [November-December] – American Airlines

Airfare Deals American Airlines Australia Flights from Chicago / Milwaukee Oneworld Sydney

Frontier and Spirit have round-trip flights from Chicago (MDW/ORD) to Dallas (DFW) for $52-$59, NONSTOP. Flights August to September. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible.

These fares do not include a free carry-on bag. Only a small personal item, like a Jansport SuperBreak backpack is free. You can avoid paying for seat selection if you accept the randomly assigned seat prior to boarding.

Click for more details and booking links Nonstop Flights: Chicago to/from Dallas $52-$59 r/t [August-September] – Frontier / Spirit

Airfare Deals Dallas Flights from Chicago / Milwaukee Frontier

Airfare Deals Flights from Chicago / Milwaukee