Icelandair has round-trip flights from Chicago (ORD) to Reykjavik (KEF) for $408-$429, NONSTOP. Flights January to March. Departures on Monday, Wednesday, and Saturday.
Category: <span>Flights from Chicago / Milwaukee</span>
Image Credits: Giuseppe Milo, Released under Creative Commons 2.0 (flickr)
Image Credits: Daniel Schwen, Creative Commons 4.0
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.
ANA and United have round-trip flights from Chicago (ORD) to Tokyo (NRT) for $1034, NONSTOP. Flights February, March, April, and September. Departures on Monday, Tuesday, and Wednesday. 7-day minimum stay required. Fares to Japan remain higher than their historical average. We expect prices to be lower next year as the region reopens to tourism.
Hopper is offering $35 or $100 off certain select flights. Sale ends 11/30/2022 at 2:00 AM.
You may want to use Google Flights with our consolidated list of every domestic destination that is on sale to figure out your exact dates and destination, then use Hopper for the additional discount. Book via their app (link).
Image Credits: Tobias Lindman, Creative Commons 2.0 (flickr)
American Airlines has round-trip flights from Milwaukee (MKE) to Providenciales, Turks & Caicos Islands (PLS) for $327-$337 with a connection. Flights January to March. Very few weekends available. Origin/Destination reversible.
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.
Image Credits: Ville-Matti Kaartinen, Creative Commons 2.0 (flickr)
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.
Image Credits: Thomas Hawk, Creative Commons 2.0 (flickr)
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.
Image Credits: Alan Stark, Creative Commons 2.0 (wikipedia)
United has round-trip flights from Chicago (ORD) to Phoenix (PHX) for $138-$158, NONSTOP. Flights December to March. Extended weekends available. Origin/Destination reversible.
jetBlue has a Cyber Monday coupon code for $50 off one-way flights when the flight is more than +$100. More details are on the jetBlue promo page (linked).