Category: <span>Flights from Chicago / Milwaukee</span>

Airfare Deals Austrian Flights from Chicago / Milwaukee Zagreb

Icelandair has round-trip flights from Chicago (ORD) to Helsinki or Zurich (HEL/ZRH) for $435-$487 with a connection. Flights October to April. Extended weekends available.

Note: Some small OTAs on Skyscanner have this for about -$25 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.

Click for more details and booking links Cheap Flights: Chicago to Helsinki or Zurich $452-$487 r/t [October-April] – Icelandair

Airfare Deals Flights from Chicago / Milwaukee Helsinki IcelandAir

Airfare Deals Flights from Chicago / Milwaukee Knoxville Star Alliance United

Airfare Deals Flights from Chicago / Milwaukee Palm Springs Star Alliance United

American Airlines, British Airways, and Iberia have round-trip flights from Chicago (ORD) to Barcelona (BCN) for $489, NONSTOP. Flights September to October. Departures on Monday, Tuesday, Wednesday, and Sunday. 7-day minimum stay required. Flight may operate as a Oneworld code-share.

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.

Click for more details and booking links Nonstop Flights: Chicago to Barcelona $489 r/t [September-October] – American Airlines / British Airways / Iberia

Airfare Deals American Airlines Barcelona British Airways Flights from Chicago / Milwaukee Iberia Oneworld

Air India has round-trip flights from Chicago (ORD) to New Delhi, Bengaluru, or Hyderabad (DEL, BLR, HYD) for $628-$698. Flights in September, January, February, and March. 7-day minimum stay required. Flights to/from New Delhi are NONSTOP. Other destinations have a connection in New Delhi.

Note: Some small OTAs on Skyscanner 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.

Click for more details and booking links Cheap Flights: Chicago to New Delhi, Bengaluru, or Hyderabad $628-$698 r/t [Sep, Jan-Mar] – Air India

Air India Airfare Deals Flights from Chicago / Milwaukee New Delhi

Airfare Deals Flights from Chicago / Milwaukee Nebraska Omaha Star Alliance United

Scandinavian Airlines has round-trip flights from Chicago (ORD) to Bologna (BLQ) for $409-$459 with a connection. Flights October to December. Extended weekends available.

Note: Some small OTAs on Skyscanner 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.

Click for more details and booking links Cheap Flights: Chicago to Bologna, Italy $409-$459 r/t [October-December] – Scandinavian Airlines

Airfare Deals Bologna Flights from Chicago / Milwaukee Scandinavian Airlines

American Airlines and United have round-trip flights from Chicago (ORD) to Portland, Maine or Nashville (PWM, BNA) for $118-$128, NONSTOP. Flights between August and November. 

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.

Click for more details and booking links Nonstop Flights: Chicago to Portland, Maine or Nashville $118-$128 r/t [September-October] – American Airlines / United

Airfare Deals American Airlines Flights from Chicago / Milwaukee Maine Oneworld Portland

American Airlines and United have round-trip flights from Chicago (ORD) to Pittsburgh or Columbus (PIT, CMH) for $178-$188, NONSTOP. Flights August to November. Extended weekends available. Origin/Destination reversible.

Regular Economy. Not Basic. A Carry-on bag, seat selection, and also a personal item is allowed without fees on United and American.

Click for more details and booking links Nonstop Flights: Chicago to/from Pittsburgh or Columbus, Ohio $178-$188 r/t [August-November] – American Airlines / United

Airfare Deals American Airlines Flights from Chicago / Milwaukee Oneworld Pittsburgh Star Alliance United