American has round-trip flights from Chicago (ORD) to New York (LGA) starting at $79, NONSTOP. $40 each-way. Flights scattered October to February. Most availability is in January. Origin/Destination reversible. Holiday blackouts apply.
Category: <span>Oneworld</span>
Image Credits: Thomas Hawk, Creative Commons 2.0 (flickr)
Image Credits: m01229, Creative Commons 2.0 (flickr)
[10/13/2017 @ 2:29 PM CT] Old post clean-up. Fare gone. Deal expired.
American has round-trip flights from Chicago (ORD) to Minneapolis (MSP) starting at $81, NONSTOP. $40 each-way. Holiday blackouts apply. Flights September to February. Origin/Destination reversible.
Note: Most return flights in September and October are early morning.
Image Credits: Katie Haugland Bowen
[10/13/2017 @ 2:29 PM CT] Old post clean-up. Fare gone. Deal expired.
American has round-trip flights from Chicago (ORD) to Dallas (DFW), Houston (IAH), Atlanta (ATL), or Denver (DEN) starting at $82, NONSTOP. $42-$50 each-way. Holiday blackouts apply. Flights scattered September to February. Origin/Destination reversible. See full post for specific date ranges.
Image Credits: paul bica, Creative Commons 2.0 (Flickr)
[08/31/2017 @ 12:12 PM CT] Fare gone. Removing from deal list.
Virgin Australia and Qantas have round-trip flights from New York (JFK) to Sydney (SYD) or Melbourne (MEL) starting at $855 with a connection. Flights February to June. 7-day minimum stay required. Holiday blackouts apply. Australian ETA (a Visa) required.
Note: Book on Priceline. Other websites have this priced at $956.
Image Credits: Bernt Rostad, Creative Commons 2.0
[08/24/2017 @ 8:00 PM CT] Fare gone. Removing from deal list.
American Airlines has round-trip flights from New York (LGA/JFK) to San Francisco (SFO) for $218 with a connection. $109 each-way. Flights from September to April. Origin/Destination reversible.
Image Credits: Alan Stark, Creative Commons 2.0 (wikipedia)
American has round-trip flights from Chicago (ORD) to Phoenix (PHX) starting at $117, NONSTOP. $59 each-way. Flights September to February. Origin/Destination reversible. Holiday blackouts.
Note: Very few flights in September and November.
Image Credits: Plashing Vole, Creative Commons 2.0 (flickr)
[09/01/2017 @ 1:34 PM CT] Mostly sold out. Removing from deal list.
American has round-trip flights from Chicago (ORD) to Austin (AUS) starting at $97, NONSTOP. $49 each-way. Flights scattered August to September. Origin/Destination reversible.
Click for more details and booking links Nonstop Flights: Chicago to/from Austin $97 r/t – American
Image Credits: Bernt Rostad, Creative Commons 2.0
American has round-trip flights from Chicago (ORD) to San Francisco (SFO) starting at $111, NONSTOP. $55 each-way. Flights scattered November to February. Origin/Destination reversible. Holiday blackouts apply.
[08/29/2017 @ 1:11 PM CT] Old post clean-up. Fare gone. Removing from deal list.
Southwest has round-trip flights from Chicago (MDW) to New Orleans (MSY) for $91 , NONSTOP. $46 each-way. Flights Tuesdays, Wednesdays, November to February. Origin/Destination reversible. Holiday blackouts apply.
Note: You can save an additional $100 if you purchase your Flight+Hotel together as a package on Southwest Vacations and use the SAVENOWUS coupon-code at checkout. Coupon expires 08/21/17. Before you commit, always compare the prices of the individual Flights and Hotel with other hotel booking sites like Hotels.com.
Image Credits: Cacophony, Creative Commons
[08/29/2017 @ 1:11 PM CT] Old post clean-up. Fare gone. Removing from deal list.
Southwest has round-trip flights from Chicago (MDW) to Portland (PDX) for $140, NONSTOP. $70 each-way. Flights Tuesdays, Wednesdays, November to February. Origin/Destination reversible. Holiday blackouts apply.
Image Credits: Ingfbruno, Creative Commons 3.0
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
Image Credits: Chris Ford, Creative Commons 2.0 (flickr)
[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
Image Credits: Ricardo Diaz, Creative Commons 2.0
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.
Image Credits: Thomas Hawk, Creative Commons 2.0 (flickr)
[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.
Image Credits: Raging Wire, Creative Commons 2.0 (flickr)
[08/17/2017 @ 10:48 PM CT] Deal is back on.
American has round-trip flights from New York (LGA) to Dallas (DFW) for $81-$111, NONSTOP. $40-$55 each-way. Flights on Tuesday, Wednesday, Saturdays, November thru February. Origin/Destination reversible. Holiday blackouts apply.
[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
Image Credits: DAVID ILIFF. License: CC-BY-SA 3.0
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.
Image Credits: Daniel Schwen, Creative Commons 4.0
[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.
Image Credits: Nrbelex, Creative Commons 2.0
[08/09/2017 @ 12:45 PM CST] Fare gone. Removing from deal list for now.
American has round-trip flights from New York (LGA) to Atlanta (ATL) starting at $93 , NONSTOP. $45-$47 each-way. Flights Tuesday, Wednesday, Saturday, January and February. Origin/Destination reversible.
Image Credits: Kuyler McComas, Creative Commons 2.0 (Flickr)
[08/08/2017 @ 2:28 AM CST] Fare gone. Removing from deal list.
American has round-trip flights from New York (EWR) to Belize (BZE) for $263, with a connection. Flights scattered from late-January to February. Availability of dates is very limited. Stick to the example dates listed in this post.