United has round-trip flights from Chicago (ORD) to Punta Cana, Dominican Republic (PUJ) for $340-$353, NONSTOP. Flights March to May. Very few extended weekends available.
Category: <span>Flights from Chicago / Milwaukee</span>
Aeromexico and United have round-trip flights from Chicago (ORD) to Mexico City (MEX) for $281-$294, NONSTOP. Flights February to September. Weekends available.
Some small OTAs on Skyscanner have this for as low as $276; which is cheaper than the airline.
American Airlines has round-trip flights from Milwaukee (MKE) to Salt Lake City (SLC) for $191 with a connection. Flights March, April, May, July, August, September, and October. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available.
American Airlines and Qantas have round-trip flights from Chicago (ORD) to Sydney, Australia (SYD) for $836-$846 with a connection. Flights February to December. Extended weekends available. No Christmas dates available.
Some small OTAs on Skyscanner have this for as low as $809; which is 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.
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.
Various carriers have round-trip flights to/from Europe at a discount today for $388-$660, NONSTOP or with a connection (see list on our website). Dates vary, use the calendar link in the post.
This list EXCLUDES most LCCs or restricted fares like TAP, SAS, Norse, French Bee, etc…
Flights to/from smaller airports may require a long connection or two stops. When you begin your search, modify your filter to remove fares that have more than one connection, some of those smaller airports ONLY have flights with bad routing.
Some small OTAs on Skyscanner and Google have this for 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.
There is a good chance that prices continue to drop if more carriers join this sale.
WestJet has round-trip flights from Chicago (ORD) to Calgary (YYC) for $159, NONSTOP. Flights February to March. Departures on Monday, Thursday, and Sunday. Extended weekends available.
Air Canada has round-trip flights from Chicago (ORD) to Toronto (YYZ) for $226-$241, NONSTOP. Flights February to June. Weekends available. Origin/Destination reversible.
American Airlines has round-trip flights from Milwaukee (MKE) to Seoul (ICN) for $809 with a connection. Flights February to March. Departures on Monday, Tuesday, Wednesday, Thursday, and Sunday. No Fridays or Saturdays. Very few extended weekends available.
A Carry-on 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.
Air Canada and United have round-trip flights from Chicago (ORD) to Tokyo (NRT/HND) for $733-$744 with a connection. Flights in February, April, September, October, November, and December. Departures on Monday, Tuesday, Wednesday, and Sunday. Holiday blackouts.
United has round-trip flights from Chicago (ORD) to Monterrey, Mexico (MTY) for $235, NONSTOP. Flights February to September. Very few weekends available.
United’s “Basic Economy” fares do not allow for a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding.
The personal item size on United is smaller (9 x 10 x 17 inches) than Frontier or Spirit (8 x 13 x 18 inches).
American Airlines, British Airways, and Iberia have round-trip flights from Chicago (ORD) to Rome (FCO) for $517-$527, NONSTOP. Flights March, April, October, and November. Extended weekends available. No Thanksgiving dates.
A Carry-on 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.
United has round-trip flights from Chicago (ORD) to Tulum (TQO) for $234-$254, NONSTOP. Flights February to March. Departures on Monday, Tuesday, Wednesday, Saturday, and Sunday.
United, Swiss, Austrian, Air Canada and various other airlines have round-trip flights from Chicago (ORD) to Athens (ATH) for $518-$545 with a connection. Flights February, March, April, October, November, and December. Very few extended weekends available. Holiday blackouts.
American Airlines and United have round-trip flights from Chicago (ORD) to Pittsburgh, Grand Rapids, or Detroit (PIT, GRR, DTW) for $137, NONSTOP. Flights February to May. No Weekends. Departures on Monday, Tuesday, Wednesday, and Thursday. Origin/Destination reversible.
A Carry-on 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.
American Airlines and Fiji Airways have round-trip flights from Chicago (ORD) to Nadi (NAN) for $897-$910 with a connection. Flights January, February, March, April, May, June, August, September, October, and November. Departures on Tuesday, Thursday, and Saturday. Extended weekends available. Dates over Thanksgiving are available.
Some small OTAs on Kayak have this for as low as $835; which is 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.
A Carry-on 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.
American Airlines has round-trip flights from Chicago (ORD) to Sydney or Melbourne, Australia (SYD, MEL) for $826-$884 with a connection. Flights January to December. Extended weekends available. No Christmas dates available.
A Carry-on 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.
United, Southwest, and American Airlines have round-trip flights from Chicago (ORD) to Austin (AUS) for $177, NONSTOP. Flights February to May. No Weekends. Departures on Monday, Tuesday, Wednesday, and Thursday. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on Southwest and American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Delta, Aeromexico, and United have round-trip flights from Chicago (ORD) to Mexico City (MEX) for $281-$295, NONSTOP. Flights February to September. Weekends available.
Flight may operate as an Aeromexico / Delta code-share.
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.
United’s “Basic Economy” fares do not allow for a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding.
The personal item size on United is smaller (9 x 10 x 17 inches) than Frontier or Spirit (8 x 13 x 18 inches).
United has round-trip flights from Chicago (ORD) to Athens (ATH) for $587, NONSTOP. Flights in May. Departures on Sunday. 9-day minimum stay required. Very limited set of dates available.
We recently posted Chicago – Athens for $536-$553 round-trip, WITH a connection. That deal has more availability (Jan-May, Sep-Nov). This post focuses on NONSTOP fares with limited availability.
Hawaiian and Alaska Airlines have round-trip flights from Milwaukee (MKE) to Kailua (KOA) for $381-$407 with a connection. Flights January, February, March, May, August, September, October, and November. No Saturday departures. Very few extended weekends available. No Thanksgiving dates.
Some small OTAs on Skyscanner have this for as low as $364 which is 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.