American Airlines has round-trip flights from Chicago (ORD) to Saint Croix (STX) for $309-$319 with a connection. Flights August to October. No Wednesday departures. Very few extended weekends available. Early morning “Red-Eye” departures.
Category: <span>Flights from Chicago / Milwaukee</span>
Lufthansa has round-trip flights from Chicago (ORD) to Helsinki (HEL) for $521 with a connection. Flights October to March. 7-day minimum stay required.
Lufthansa “Light Fares” allow for a carry-on bag (17.6-lbs @ 21.6 x 15.7 x 9 inches) and also a very small personal item such as a laptop bag (11.8 x 15.7 x 3.9 inches). The weight limit will probably be the limiting factor for those of you who wish to avoid bag fees. Prioritizing heavier items in your “personal item” may be a good way to lighten your carry-on bag. You can avoid seat selection fees by accepting the randomly assigned seat at the gate.

Nonstop Flights: Chicago to/from Calgary $220-$244 r/t [August-October] – United / American Airlines
United, WestJet, Air Canada, and American Airlines have round-trip flights from Chicago (ORD) to Calgary (YYC) for $220-$244, NONSTOP. Flights August to October. Weekends available. Origin/Destination reversible.
Air India has round-trip flights from Chicago (ORD) to New Delhi (DEL) for $676, NONSTOP. Flights in October, January, February, March, and April. Departures on Monday, Tuesday, Wednesday, and Sunday.
Some small OTAs on Skyscanner and Google have this for $638; cheaper than the airline. 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.
Icelandair has round-trip flights from Chicago (ORD) to Dublin (DUB) for $466 with a connection. Flights November to March. Departures on Monday, Tuesday, Wednesday, and Sunday. No Thanksgiving dates.
Some small OTAs on Skyscanner and Crystal Travel have this for $439; cheaper than the airline. 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. We advise against booking on Crystal Travel due to bad reviews.
Chase has increased the sign-up bonus for the United℠ Explorer Card. Read the full blog post for more details.
United and American Airlines have round-trip flights from Chicago (ORD) to Punta Cana, Dominican Republic (PUJ) for $268-$307, NONSTOP or with connections. Flights in June, August, and September. Very few extended weekends available. Origin/Destination reversible.
American Airlines and United have round-trip flights from Chicago (ORD) to Santiago de Queretaro (QRO) for $354-$373 with a connection. Flights August to October. Extended weekends available. Origin/Destination reversible.
Air India has round-trip flights from Chicago (ORD) to New Delhi, Hyderabad, or Bengaluru (DEL, HYD, BLR) for $676. New Delhi fares are NONSTOP, others have a connection. Flights in October, January, February, and March. Departures on Monday, Tuesday, Wednesday, and Sunday.
Some small OTAs on Skyscanner and Google have this for $613; cheaper than the airline. 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.
American Airlines has round-trip flights from Chicago (ORD) to Houston or Phoenix (IAH, PHX) for $148-$173, NONSTOP. Flights August to November. Departures on Tuesday, Wednesday, Thursday, Saturday, and Sunday. Extended weekends available. Origin/Destination reversible. No Thanksgiving dates. Most flights are on Tuesdays, Wednesdays, or Saturdays.
Note: Houston is about $148 / Phoenix is about $168. Price range may fluctuate by +/- $10 as deal ages.