American Airlines has round-trip flights from Chicago (ORD) to Key West (EYW) for $208, NONSTOP. Flights January to March. No Saturday departures. Extended weekends available.
Category: <span>Flights from Chicago / Milwaukee</span>
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Image Credits: Chris Yunker, Creative Commons 2.0
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.
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American Airlines has round-trip flights from Chicago (ORD) to Kahului (OGG) for $343 with a connection. Flights January to February. No Weekends. Departures on Monday, Tuesday, Wednesday, and Thursday. Origin/Destination reversible.
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Southwest has round-trip flights from Chicago (MDW) to San Francisco or Los Angeles (SFO, LAX) for $132-$198. $66-$99 each-way. Flights August to November. Limited availability. Origin/Destination reversible.
San Francisco flights have a connection. Los Angeles flights are NONSTOP.
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United and Southwest have round-trip flights from Chicago (ORD/MDW) to Philadelphia (PHL) for $138-$158, NONSTOP. Flights August to November. Very few weekends available. Origin/Destination reversible.
Southwest allows for 2 bags without fee.
United’s “Basic Economy” fares do not allow for a free carry-on bag.
Image Credits: Rambla, Creative Commons 2.0 (wikipedia)
Iberia, Finnair, and British Airways have round-trip flights from Chicago (ORD) to Barcelona or Madrid (BCN, MAD) for $489-$507, NONSTOP. Flights October to March. Departures on Monday, Tuesday, Wednesday, and Sunday. 7-day minimum stay required.
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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.
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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.
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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.
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Southwest has round-trip flights from Chicago (MDW) to Dallas (DAL) for $138-$158, NONSTOP. $69-$79 each-way. Flights September to November. Weekends available. Origin/Destination reversible. Midweek flights are the cheapest.
A Carry-on bag, two checked bags, and also a personal item is allowed for free on Southwest.