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

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

Air France Airfare Deals Delta Flights from Chicago / Milwaukee Luxembourg SkyTeam

Airfare Deals Delta Flights from Chicago / Milwaukee Frankfurt SkyTeam Virgin Atlantic

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.

Click for more details and booking links Cheap Flights: Chicago to Athens, Barcelona, Helsinki, Madrid, Milan, Paris, Naples, Zurich, Vienna, or Rome $367-$455 r/t [Dates vary, use example date list] – Delta / Virgin Atlantic / Air France

Air France Airfare Deals Athens Delta Flights from Chicago / Milwaukee SkyTeam Virgin Atlantic

Airfare Deals Flights from Chicago / Milwaukee Southwest St. Louis Star Alliance United

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.

Click for more details and booking links Nonstop Flights: Chicago to/from New York, Cleveland, Detroit, or Nashville $77-$117 r/t [May-October] – American Airlines / United / Southwest

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

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

Airfare Deals Flights from Chicago / Milwaukee Maine Portland Star Alliance United

Airfare Deals Flights from Chicago / Milwaukee IcelandAir Stockholm

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.

Click for more details and booking links Nonstop Flights: Chicago to/from Albuquerque, Myrtle Beach, Pensacola, or Panama City FL $135-$155 r/t [May-November] (No Thanksgiving) – United / American Airlines

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

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

Airfare Deals Bangkok Flights from Chicago / Milwaukee Star Alliance United

Airfare Deals Alaska Airlines Delta Flights from Atlanta Flights from Chicago / Milwaukee Flights from Denver Flights from Los Angeles Flights from Milwaukee Flights from New York Flights from Phoenix Flights from Portland Flights from Seattle San Francisco SkyTeam Star Alliance United

Airfare Deals Baltimore Flights from Chicago / Milwaukee Southwest

Airfare Deals Boston Flights from Chicago / Milwaukee Southwest

Airfare Deals Berlin Flights from Chicago / Milwaukee IcelandAir

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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)

Click for more details and booking links Free: Unfiltered daily Patreon recap for New York, Los Angeles + metro area, Chicago, Milwaukee, Seattle, Everett, and Portland – May 04, 2025 @ 02:38 PM CT

Airfare Deals Flights from Chicago / Milwaukee Flights from Los Angeles Flights from Milwaukee Flights from New York Flights from Portland Flights from Seattle

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

Airfare Deals American Airlines Austin Flights from Chicago / Milwaukee Oneworld Southwest

Aer Lingus Airfare Deals Flights from Chicago / Milwaukee IcelandAir Manchester