United has round-trip flights from Chicago (ORD) to Punta Cana (PUJ) for $224-$235, NONSTOP. Flights October, November, January, and February. Departures on Monday, Tuesday, and Sunday. United charges about $35 each-way for a checked-bag.
Category: <span>Flights from Chicago / Milwaukee</span>
Image Credits: Niedźwiadek78, Creative Commons
American Airlines and United have round-trip flights from Chicago (ORD) to Las Vegas (LAS) for $97, NONSTOP. Flights October to December. Departures on Monday, Tuesday, Wednesday, Saturday, and Sunday. Very few extended weekends available. Origin/Destination reversible.
Carry-on bag is allowed for free on American. United charges a $35 fee for checked-bags each-way. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Image Credits: Atilin, Creative Commons 3.0
JetBlue has round-trip flights from Chicago (ORD) to Aruba (AUA) for $266 with a connection. Flights in October. No Saturday departures. Very few extended weekends available.
SAS and United have round-trip flights from Chicago (ORD) to Amsterdam (AMS) for $373 with a connection on SAS or $477 NONSTOP on United. Flights October to June. Extended weekends available.
Carry on bag with a maximum weight of 18 lbs is allowed for free on SAS. United flights are NONSTOP and allow for a regular weight carry-on bag. You can avoid seat selection fees by accepting the randomly assigned seat at the gate.
Note that TAP has flights available for “$316” but those don’t include a carry-on bag. TAP charges $95! (each-way!) to check a regular sized bag. You should avoid the TAP fares because they will cost more than the NONSTOP UA flight once you add in the fees.
Image Credits: Roman Königshofer, Creative Commons 2.0 (flickr)
American Airlines has round-trip flights from Milwaukee (MKE) to San Jose, Costa Rica (SJO) for $238-$241 with a connection. Flights October, November, December, February, March, April, May, July, and August. Weekends available. Origin/Destination reversible.
Image Credits: Kuyler McComas, Creative Commons 2.0 (Flickr)
American Airlines has round-trip flights from Milwaukee (MKE) to Belize City (BZE) for $289-$292 with a connection. Flights October to August. Weekends available. Origin/Destination reversible.
Image Credits: js hsu, Creative Commons 2.0 (flickr)
Delta has round-trip flights from Chicago (ORD) to Anchorage or Fairbanks (ANC, FAI) for $191-$202 with a connection. Flights October to December. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible.
Carry-on bag is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Image Credits: Howard Ignatius, Creative Commons 2.0 (flickr)
United has round-trip flights from Chicago (ORD) to San Francisco, Seattle, or Portland Oregon (SFO, SEA, PDX) for $103-$134, NONSTOP. Flights October to December. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible.
Image Credits: scarhead101, Creative Commons 2.0 (flickr)
American Airlines and United have round-trip flights from Chicago (ORD) to Cozumel (CZM) for $167-$217, NONSTOP or with connections. Flights September to February. Weekends available. Origin/Destination reversible.
Image Credits: Rdsmith4, Creative Commons 2.5 (wikipedia)
American Airlines and United have round-trip flights from Chicago (ORD) to Philadelphia (PHL) for $97, NONSTOP. Flights September to November. No Sunday departures. Very few weekends available. Origin/Destination reversible.
Carry-on bag is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.