American Airlines has round-trip flights from Portland (PDX) to Chicago (ORD) for $179, NONSTOP. Flights in May. Very few weekends available. Origin/Destination reversible.
Category: <span>Flights from Chicago / Milwaukee</span>
Image Credits: Daniel Schwen, Creative Commons 4.0
Image Credits: Benh LIEU SONG, Creative Commons 3.0 (Wikipedia)
Air France, KLM, and Delta have round-trip flights from Chicago (ORD) to Luxembourg (LUX) for $385-$411 with a connection. Flights August to March. Departures on Monday, Tuesday, Wednesday, and Sunday. 7-day minimum stay required.
Image Credits: Mylius, Creative Commons 3.0
Delta and Virgin Atlantic have round-trip flights from Chicago (MDW/ORD) to Frankfurt or Munich (FRA, MUC) for $462-$496 with a connection. Flights in August, October, November, December, January, February, and March. 7-day minimum stay required. Holiday blackouts.
Image Credits: Nikthestoned, Creative Commons 3.0
Delta, Virgin Atlantic, and Air France have round-trip flights from Chicago (ORD) to Athens, Barcelona, Helsinki, Madrid, Milan, Paris, Naples, Zurich, Vienna, or Rome (ATH, BCN, HEL, MAD, MXP, CDG, NAP, ZRH, VIE, FCO) for $367-$455 with a connection. Dates vary depending on destination, use the example date list for exact dates. Holiday blackouts.
Flights to Paris are NONSTOP.
Image Credits: Philip Leara (Public Domain)
Southwest and United have round-trip flights from Chicago (MDW/ORD) to St. Louis or Pittsburgh (STL, PIT) for $77-$138, NONSTOP. Flights June to October. Extended weekends available. Origin/Destination reversible.
Image Credits: Thomas Hawk, Creative Commons 2.0 (flickr)
American Airlines, Southwest, and United have round-trip flights from Chicago (ORD/MDW) to New York, Cleveland, Detroit, or Nashville (LGA, CLE, DTW, BNA) for $77-$117, NONSTOP. Flights are between May to October. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on AA. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Image Credits: Jasen Miller, Creative Commons 2.0 (flickr)
United has round-trip flights from Chicago (ORD) to Colorado Springs or Fort Myers (COS, RSW) for $135-$144, NONSTOP. Flights June to November. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible. No Thanksgiving dates.
Image Credits: Captured Visuals, Creative Commons 2.0 (flickr)
United has round-trip flights from Chicago (ORD) to Portland, Maine (PWM) for $135, NONSTOP. Flights May to November. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible. No Thanksgiving dates.
Image Credits: Pedro Szekely, creative commons 2.0 (flickr)
Icelandair has round-trip flights from Chicago (ORD) to Stockholm or Helsinki (ARN, HEL) for $393-$421 with a connection. Flights August to March. Extended weekends available.
Some small OTAs on Skyscanner have this for as low as $365; which is cheaper than the airline.
Image Credits: Dan J, creative commons 2.0 (flickr)
United and American Airlines have round-trip flights from Chicago (ORD) to Albuquerque, Myrtle Beach, Pensacola, or Panama City FL (ABQ, MYR, PNS, ECP) for $135-$155, NONSTOP. Flights May to November. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible. No Thanksgiving dates.
Image Credits: Ville-Matti Kaartinen, Creative Commons 2.0 (flickr)
American Airlines and British Airways have round-trip flights from Chicago (ORD) to Helsinki (HEL) for $481-$495 with a connection. Flights October to March. Departures on Monday, Tuesday, Wednesday, and Sunday. 7-day minimum stay required.
Image Credits: Kevin Poh, Creative Commons 2.0
United has round-trip flights from Chicago (ORD) to Bangkok (BKK) for $737-$805 with a connection. Flights August to November. Departures on Monday, Tuesday, Wednesday, Thursday, and Sunday. No Fridays or Saturdays. Origin/Destination reversible. No Thanksgiving dates.
Southwest, American, and Delta have round-trip flights to/from various destinations in the USA at a discount today for $97-$189, NONSTOP or with a connection. Dates vary, use the linked calendar. Flights are mostly on Tuesdays, Wednesdays, and Saturdays. Origin/Destination reversible.
Image Credits: Raging Wire, Creative Commons 2.0 (flickr)
Southwest has round-trip flights from Chicago (MDW) to Baltimore or Dallas (BWI, DAL) for $145-$171, NONSTOP. Flights May to August. No Sunday departures. Some weekends available. Origin/Destination reversible.
Image Credits: Ingfbruno, Creative Commons 3.0
Southwest has round-trip flights from Chicago (MDW) to Boston (BOS) for $92-$105, NONSTOP. Flights May to August. Extended weekends available. Origin/Destination reversible.
Image Credits: Daniel Mennerich, Creative Commons 2.0 (flickr)
Icelandair has round-trip flights from Chicago (ORD) to Berlin (BER) for $508-$522 with a connection. Flights July to March. Extended weekends available.
Some small OTAs on Skyscanner have this for as low as $480; which is cheaper than the airline.
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This post is the unfiltered daily Patreon recap of New York, Los Angeles + metro area, Chicago, Milwaukee, Seattle, Everett, and Portland airfare as of May 04, 2025 @ 02:38 PM Central Time. There are currently (1252) fares that are below (or near) their 6-month moving average.
The (1252) fares found today are more than the 30-day average of (1167) per day. This means that deal availability is trending up.
The airfare count per region is as follows:
New York/Newark (291)
Los Angeles area (360)
Chicago/Milwaukee (219)
Seattle/Everett (195)
Portland (187)
Image Credits: Benh LIEU SONG, Creative Commons 3.0 (Wikipedia)
American Airlines and British Airways have round-trip flights from Chicago (ORD) to Luxembourg (LUX) for $586 with a connection. Flights October to March. Departures on Monday, Tuesday, Wednesday, and Sunday. 7-day minimum stay required.
Image Credits: Plashing Vole, Creative Commons 2.0 (flickr)
Southwest and American Airlines have round-trip flights from Chicago (ORD/MDW) to Austin (AUS) for $159, NONSTOP. Flights June to August. Departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible.
Image Credits: Stephen - Creative Commons 2.0 (flickr)
Icelandair and Aer Lingus have round-trip flights from Chicago (ORD) to Manchester (MAN) for $522-$563 with a connection. Flights August to March. Extended weekends available.
Some small OTAs on Skyscanner have this for as low as $495; which is cheaper than the airline.