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

Airfare Deals Flights from Chicago / Milwaukee IcelandAir Reykjavik

This list was updated and refreshed on December 02, 2022 @ 12:05 PM Central Time. (Most of the best deals have expired and been removed. This is the last update to this post.)

Alaska Airlines, Frontier, Southwest, United, and Delta have domestic flights on sale with a price range between $52-$218. Flight dates are mostly between January to March.

Frontier sale has been added 11/29, those fares have additional fees, and are marked on this list as “Bare Economy”.

This is a consolidated list of every fare under $218 that is also lower than the 6-month moving average. We use this to filter out deals that aren’t at a significant discount. We will update this page periodically on our website (escape.flights), so check back often.

Click for more details and booking links Updated Holiday Sale: Chicago and Milwaukee to USA Domestic (Boston, New York, Seattle, San Francisco, New Orleans, Austin, +more) $52-$218 r/t [January-March] – Alaska Airlines / Delta / Southwest / United / Frontier

Airfare Deals Flights from Chicago / Milwaukee Flights from Milwaukee

Airfare Deals ANA Flights from Chicago / Milwaukee Star Alliance Tokyo

Administrative Airfare Deals 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

Airfare Deals American Airlines Flights from Chicago / Milwaukee Flights from Milwaukee Oneworld Providenciales Turks & Caicos Islands

American Airlines and United have round-trip flights from Chicago or Milwaukee (ORD/MKE) to Honolulu or Maui (HNL, OGG) for $389-$404 with a connection. Flights January to February. No Weekends. 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.

Click for more details and booking links Cheap Flights: Chicago and Milwaukee to/from Honolulu or Maui, Hawaii $389-$404 r/t [January-February] – American Airlines / United

Airfare Deals American Airlines Flights from Chicago / Milwaukee Honolulu Oneworld

Icelandair has round-trip flights from Chicago (ORD) to Helsinki (HEL) for $366-$397 with a connection. Flights January to February. 7-day minimum stay required.

A Carry on bag (20-lbs @ 21.6 x 15.7 x 7.8 inches) and a personal item (15.7 x 11.8 x 5.9 inches) is allowed for free on Icelandair. You can avoid seat selection fees by accepting the randomly assigned seat at the gate.

Click for more details and booking links Cheap Flights: Chicago to Helsinki $366-$397 r/t [January-February] – Icelandair

Airfare Deals Flights from Chicago / Milwaukee Helsinki IcelandAir

Delta, United, and American have round-trip flights from Chicago (ORD) to New York (JFK) for $138, NONSTOP. Flights January to May. Very few weekends available. Origin/Destination reversible.

A Carry-on bag and also a personal item is allowed for free on Delta and 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/from New York $138 r/t [January-May] – Delta / United / American

Airfare Deals Delta Flights from Chicago / Milwaukee Flights from New York New York SkyTeam

Airfare Deals Flights from Chicago / Milwaukee Flights from Phoenix Phoenix Star Alliance United

Airfare Deals 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