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

Airfare Deals Boston Delta Flights from Chicago / Milwaukee Flights from Milwaukee SkyTeam

Image Credits: Katie Haugland Bowen

Airfare Deals Flights from Chicago / Milwaukee

Airfare Deals Delta Flights from Chicago / Milwaukee Flights from New York New York/Newark SkyTeam Star Alliance United

Airfare Deals Flights from Chicago / Milwaukee Ottawa Star Alliance United

Airfare Deals Flights from Chicago / Milwaukee Rome Star Alliance United

Tap Air Portugal has round-trip flights from Chicago (ORD) to Porto (OPO) for $458-$466 with a connection. Flights October to May. Weekends available.

Carry on bag with a maximum weight of 17.6 lbs is allowed for free on TAP. You can avoid seat selection fees by accepting the randomly assigned seat at the gate. Upgrading to a higher fare class that includes a carry-on bag for $65 may be cheaper than booking the “Discount” fare with the added $95 carry-on bag fee.

Flights on TAP allow for a free stopover (up to 5-days) in their hub city. This will be useful if you want to spend time exploring Porto or Lisbon before heading to your final destination. Link: More details on the TAP stopover program.

Click for more details and booking links Cheap Flights: Chicago to Porto $458-$466 r/t [October-May] – Tap Air Portugal

Airfare Deals Flights from Chicago / Milwaukee Porto TAP Air Portugal

Royal Jordanian has round-trip flights from Chicago (ORD) to Tel Aviv-Yafo (TLV) for $625 with a connection. Flights October to December. Departures on Thursday, Saturday, and Sunday.

Some small OTAs on Skyscanner have this for cheaper than the airline, about $586. 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 Tel Aviv-Yafo $586-$625 r/t [October-December] – Royal Jordanian

Airfare Deals Flights from Chicago / Milwaukee Royal Jordanian Tel Aviv-Yafo

Airfare Deals Delta Flights from Chicago / Milwaukee Saint Croix SkyTeam

Delta, Air India, United, and Lufthansa have round-trip flights from Chicago (ORD) to Bengaluru (BLR) for $686-$693 with a connection. Flights October, November, February, March, April, and May. No Saturday departures. Extended weekends available.

Delta fares are Main Cabin. Not Basic. Carry-on, checked bag, and seat selection are allowed without additional fee.

Click for more details and booking links Cheap Flights: Chicago to Bengaluru, India $686-$693 r/t [Oct-Nov, Feb-May] – Delta / Air India / United / Lufthansa

Air India Airfare Deals Bengaluru Flights from Chicago / Milwaukee Lufthansa Star Alliance United

Airfare Deals Flights from Chicago / Milwaukee Milan Star Alliance United