JetBlue has round-trip flights from Chicago (ORD) to Port of Spain (POS) for $284-$298 with a connection. Flights February to March. Departures on Monday, Wednesday, Thursday, and Sunday. Very few extended weekends available. Origin/Destination reversible. Most departures are early in the morning, around 5:30 am.
Category: <span>Flights from Chicago / Milwaukee</span>
Image Credits: Taran Rampersad, Creative Commons (Flickr)
Image Credits: John W, Creative Commons 2.0 (flickr)
JetBlue has round-trip flights from Chicago (ORD) to Sint Maarten or Nassau (SXM, NAS) for $210-$256 with a connection. Flights January to March. Very few weekends available. Origin/Destination reversible. Most of the cheap departures are in the early morning, around 5:30 am.
Image Credits: Breezy Baldwin, Creative Commons 2.0
JetBlue and United have round-trip flights from Chicago (ORD) to San Juan, Puerto Rico (SJU) for $159-$183 with a connection. Flights February to March. No Wednesday departures. Origin/Destination reversible. Flights are early morning, or late night Red-Eye flights.
Image Credits: Ted McGrath, Creative Commons 2.0 (flickr)
Delta has round-trip flights from Milwaukee (MKE) to Panama City, Panama (PTY) for $336 with a connection. Flights February to November. Weekends available. Origin/Destination reversible.
Image Credits: David Evers, Creative Commons 2.0
United, Finnair, Iberia, British Airways and various other airlines have round-trip flights from Chicago (ORD) to Rome (FCO) for $448-$470 with a connection. Flights January, February, March, April, May, September, October, and November. Extended weekends available. A -$50 price drop from a few days ago.
Image Credits: Daniel Mennerich, Creative Commons 2.0 (flickr)
SAS has round-trip flights from Chicago (ORD) to Berlin (BER) for $388-$413 with a connection. Flights March, April, May, August, September, and October. Departures on Tuesday, Wednesday, Thursday, and Sunday. Very few 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).
Image Credits: Akrobaten gang og sykkelbro, Creative Commons 3.0
Finnair, SAS, American Airlines, British Airways and various other airlines have round-trip flights from Chicago (ORD) to Oslo (OSL) for $442-$451 with a connection. Flights March, April, May, September, October, and November. Departures on Monday, Tuesday, Wednesday, and Sunday. 7-day minimum stay required.
Image Credits: Howard Ignatius, Creative Commons 2.0 (flickr)
Alaska Airlines has round-trip flights from Milwaukee (MKE) to Seattle (SEA) for $138, NONSTOP. Flights January to March. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Extended weekends available.
Image Credits: Ville-Matti Kaartinen, Creative Commons 2.0 (flickr)
Finnair, British Airways, Iberia, American Airlines and various other airlines have round-trip flights from Chicago (ORD) to Helsinki (HEL) for $459-$472, NONSTOP. Flights January to March. Extended weekends available.
Note: Some small OTAs on Skyscanner have this for $459. 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.
Avoid the SAS fares, those have stops and fees.
Image Credits: Nikthestoned, Creative Commons 3.0
Iberia, American Airlines, and British Airways have round-trip flights from Chicago (ORD) to Athens (ATH) for $508-$544 NONSTOP, or with a connection. Flights March to April.