[08/22/2017 @ 1:40 PM CT] Mostly sold out. A few scraps left.
JetBlue has round-trip flights from Chicago (ORD) to The Turks & Caicos Islands (PLS) starting at $266 with a connection. Flights very limited, midweek, late-October to Noember. No Thanksgiving/Christmas.
United and Alliance partners have round-trip flights from Chicago (ORD) to Prague (PRG), Budapest (BUD), Warsaw (WAW), Hamburg (HAM), or Berlin (TXL) for $415-$472 with a connection. Flights August to October. May operate as a Star Alliance codeshare. 7-day minimum stay required. Holiday blackouts apply.
[08/18/2017 @ 5:02 PM CT] Fare gone. Removing from deal list.
Delta has round-trip flights from Chicago (ORD/MDW) to Frankfurt (FRA) or Munich (MUC) for $428 with a connection. Flights October to March. Flight may operate as a KLM/Air France codeshare. 7-day minimum stay required. Holiday blackouts apply.
Note: Stick to the example dates listed in this post, dates not listed here may have very long connection times.
Air Canada has round-trip flights from Chicago (ORD) to Taipei, Taiwan (TPE) for $583 with a connection. Flights September to October 2017.
Note: Book on Travelocity or Priceline, other sites have the same fare for +$100 more at the moment.
JetBlue has round-trip flights from Chicago (ORD) to Fort Lauderdale (FLL) for $89, NONSTOP. $45 each-way. Flights Tuesdays and Wednesdays, September to December. Christmas and Thanksgiving blackouts. Origin/Destination reversible.
Icelandair has round-trip flights from Chicago (ORD) to Paris (ORY) for $450 with a connection. Flights January to March 2018. Holiday Blackouts apply. No Tuesdays.
Note: United is currently matching with NONSTOP fights for $532.
Click for more details and booking links Cheap Flights: Chicago to Paris $450 r/t – Icelandair
Southwest has round-trip flights from Chicago (MDW) to Boston (BOS) for $90, NONSTOP. $45 each-way. Flights September to December. Origin/Destination reversible. Holiday blackouts apply.
Click for more details and booking links Nonstop Flights: Chicago to/from Boston $90 r/t – Southwest
[08/16/2017 @ 3:51 PM CT] Fare gone. Removing from deal list.
American has round-trip flights from Chicago (ORD) to Apsen (ASE) starting at $345, NONSTOP. Flights scattered January to February. Weekends available.
Click for more details and booking links Nonstop Flights: Chicago to Aspen $345-$385 r/t – American
Southwest has round-trip flights from Chicago (MDW) to Cancun (CUN) for $226, NONSTOP. $110-$118 each-way. Flights depart SUN-TUE and return TUE-FRI November to January. No Saturdays.
Note: You can save an additional $200 if you purchase your Flight+Hotel together as a package on Southwest Vacations and use the SAVENOWINT coupon-code at checkout.
[08/17/2017 @ 10:48 PM CT] Deal is back on.
American has round-trip flights from Chicago (ORD) to New York (LGA) or Baltimore (DCA/BWI) starting at $83, NONSTOP. $42-$49 each-way. Flights scattered November to February. Origin/Destination reversible. Holiday blackouts apply.
Note: Flights departing from New York and arriving in Chicago are also available due to the reversibility of the fare.
[08/15/2017 @ 3:59 PM CT] Fare gone. Removing from deal list.
Oneworld (AA/BA/Etc…) has round-trip flights from Chicago (ORD) to Brussels (BRU), Vienna (VIE), or Zurich (ZRH) starting at $464 with a connection. Flights September 2017 to May 2018. Holiday Blackouts apply. 7-day minimum stay required.
Price targets = Zurich $464 / Vienna $500 / Brussels $478
Icelandair has round-trip flights from Chicago (ORD) to Oslo (OSL) for $434 with a connection. Flights October 2017 to March 2018. Holiday Blackouts apply. No Tuesdays.
Click for more details and booking links Cheap Flights: Chicago to Oslo $434 r/t – Icelandair
American has round-trip flights from Chicago (ORD) to Los Angeles (LAX) starting at $99, NONSTOP. $50 each-way. Flights scattered November to February. Origin/Destination reversible. Holiday blackouts apply.
Note: Most departures are late-night.
[08/24/2017 @ 12:30 PM CT] Fare gone. Removing from deal list.
Icelandair has round-trip flights from Chicago (ORD) to Frankfurt (FRA) for $420 with a connection. Flights January and February 2018.
Click for more details and booking links Cheap Flights: Chicago to Frankfurt $420 r/t – Icelandair
[08/16/2017 @ 1:43 AM CT] Deal is currently offline.
SAS has round-trip flights from Chicago (ORD) to Berlin (TXL) starting at $516 with a connection. Flights scattered September to December 2017 and also February to June 2018. Holiday blackouts apply.
Click for more details and booking links Cheap Flights: Chicago to Berlin $516-$533 r/t – SAS
We have now started up our coverage of Chicago / Milwaukee airfare deals. This post covers where to find them on the site.
[11/04/2017 @ 10:15 PM CT] Old post clean-up. Fare gone. Removing from deal list.
Southwest has round-trip flights from New York (LGA) to Chicago (MDW) for $90 with a connection. $45 each-way. Flights Tuesdays and Wednesdays from September to December.
American Airlines also has a few flights scattered about, but with very low availability.
