American Airlines has round-trip flights from Chicago (ORD) to Belize City (BZE) for $366 with a connection. Flights December to March. Departures on Monday, Tuesday, Wednesday, and Sunday. Origin/Destination reversible. No Christmas dates available.
Category: <span>Flights from Chicago / Milwaukee</span>
Image Credits: Kuyler McComas, Creative Commons 2.0 (Flickr)
Image Credits: Roman Königshofer, Creative Commons 2.0 (flickr)
American Airlines has round-trip flights from Chicago (ORD) to San Jose, Costa Rica (SJO) for $343, NONSTOP. Flights December to February. Departures on Monday, Tuesday, Wednesday, and Sunday. No Christmas dates available.
Image Credits: Kevin Bovard, Creative Commons 2.0 (flickr)
United has round-trip flights from Chicago (ORD) to Vail, Colorado (EGE) for $211-$237, NONSTOP. Flights January to February. Very few weekends available.
Image Credits: Thomas Hawk, Creative Commons 2.0 (flickr)
United, American Airlines, and JetBlue have competing round-trip fare sales from Chicago (ORD) to New York (LGA/JFK) priced at $91-$97, NONSTOP. Flights January to March. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Origin/Destination reversible.
This is a small subset of the domestic fares on sale right now, see our previous Domestic Airfare post from yesterday (link) for a list containing about 30 more destinations.
Image Credits: Steve Dunleavy, Creative Commons 2.0 (flickr)
Southwest has round-trip flights from Chicago (MDW) to Kailua-Kona, Hawaii (KOA) for $282-$319 with a connection. Flights January to May. Departures on Monday, Tuesday, Wednesday, and Sunday. Origin/Destination reversible.
United has round-trip flights from Chicago (ORD) to Honolulu (HNL) for $284-$295 with a connection. Flights January to February. Departures on Tuesday and Wednesday. Origin/Destination reversible.
Downside is a long 5-hour connection in LAX, but I think it may be worth it at this price.
Most major domestic airlines have posted a lot of discounted round-trip flights to various destinations in the USA at a discount today for $63-$199, Nonstop or with a connection. Dates vary, use the linked calendar. Cheapest fares are mostly midweek. Most fares are reversible. Expect prices to fluctuate by +/- $20 from the number listed here throughout the day.
Most destinations have flights between January to February available. The exact ranges for each destination will vary. Use the calendar links on our website to get an idea of what dates work.
Flights to smaller airports may require a long connection or two stops. When you begin your search, modify your filter to remove fares that have more than one connection, some of those smaller airports ONLY have flights with bad routing.
American, Alaska Airlines, Delta, and United almost always end up matching and in some cases, beating, these Southwest sales when they see them. It took them about 19-hours to match the previous sale.
WE EXPECT PRICES TO DROP A BIT MORE WHEN MORE AIRLINES MATCH, BUT THESE PRICES ARE GOOD, EVEN WITHOUT ANY ADDITIONAL PRICE DROP.
If you like this style of report, it’s a subset of daily Patreon recap [link]. That recap is the unfiltered list of every fare that was priced below the 6-month moving average.
Image Credits: Moyann Brenn, Creative Commons 2.0 (flickr)
Turkish Airlines via Skyscanner has round-trip flights from Chicago (ORD) to Istanbul (IST) for $650-$699, NONSTOP. Flights January to April.
Image Credits: Donaldytong, CC-BY-SA-3.0
United and Aer Lingus have round-trip flights from Chicago (ORD) to Dublin or Rome (DUB, FCO) for $419-$441, NONSTOP. Departures on Monday, Tuesday, Wednesday, and Sunday. 7-day minimum stay required. No Christmas dates available.
Dublin flights December, January, February, March, August, and September.
Rome flights December, February, March, and August.
This is a small subset of the European fares that are on sale right now. See yesterday’s post for a list of over 30 destinations (link).
Oneworld, SAS, and Icelandair have round-trip flights to various destinations in Europe at a discount today for $288-$650, mostly with a connection. Dates vary, use the linked calendar. Cheapest fares are mostly midweek. Most fares are not reversible.
Notes: Most destinations have flights from December to May and also August and September. The exact ranges for each destination will vary. Use the Google calendar view to get an idea of what dates work.
These type of regional sales often get matched by the other major airline alliances within a day or so. If you decide to purchase, then you should continue to monitor your price afterwards, it may drop lower within the 24-hour free cancelation window allowing you to re-book a cheaper flight.
Flights to smaller airports may require a long connection or two stops. When you begin your search, modify your filter to remove fares that have more than one connection, some of those smaller airports ONLY have flights with bad routing.
If you like this style of report, it’s a subset of daily Patreon recap [link]. That recap is the unfiltered list of every fare that was priced below the 6-month moving average.
Image Credits: Furya, Creative Commons 2.0 (Wikipedia)
Scandinavian Airlines has round-trip flights from Chicago (ORD) to Copenhagen, Stockholm, or Tallinn (CPH, ARN, TLL) for $348-$446. Flights January to May. No Tuesday departures.
Copenhagen fares are NONSTOP, all other fares have a connection in Copenhagen.
Image Credits: paul bica, Creative Commons 2.0 (flickr)
Air Canada has round-trip flights from Chicago (ORD) to Toronto (YYZ) for $167-$177, NONSTOP. Flights January to April. Weekends available. Origin/Destination reversible.
Image Credits: Janel J. Díaz, Creative Commons 3.0 (wikipedia)
COPA and Avianca has round-trip flights from Chicago (ORD) to Santiago, Chile (SCL) for $624-$650 with a connection. Flights January, February, March, April, May, June, August, and September.
Nonstop Flights: Chicago to/from Nashville $97 r/t [December-February] (Christmas dates) – Southwest
Nonstop Flights: Chicago to/from Nashville $97 r/t [December-February] (Christmas dates) – Southwest
Southwest has round-trip flights from Chicago (MDW) to Nashville (BNA) for $97, NONSTOP. Flights December to February. Departures on Tuesday, Wednesday, Thursday, Saturday, and Sunday. Origin/Destination reversible. Dates over Christmas are available.
Seeing some Christmas availability for this fare, which usually prices at a hefty premium.
Image Credits: Breezy Baldwin, Creative Commons 2.0
JetBlue has round-trip flights from Chicago (ORD) to San Juan, Puerto Rico (SJU) for $150-$159 with a connection. Flights February to September. Weekends available. Origin/Destination reversible.
This is the lowest I’ve seen it since July 2023.
Image Credits: Giuseppe Milo, Released under Creative Commons 2.0 (flickr)
Icelandair has round-trip flights from Chicago (ORD) to Reykjavik, Amsterdam, Copenhagen, Helsinki, or Barcelona (KEF, AMS, CPH, HEL, BCN) for $359-$476.
Reykjavik flights are Nonstop.
All other flights have a connection in Reykjavik.
Most flights are between December and May, with limited December availability, no Christmas.
Amsterdam is the most expensive fare in this list, Barcelona is the cheapest.
Some small OTAs on Skyscanner have this for cheaper than the airline. I
Image Credits: Jay Galvin, Creative Commons 2.0 (flickr)
Fiji Airways has round-trip flights from Chicago (ORD) to Nadi, Fiji (NAN) for $818-$895 with a connection. Flights January, February, April, May, August, and September. Departures on Tuesday and Saturday. Origin/Destination reversible. 7-day minimum stay required.
Some small OTAs on Skyscanner have this for as low as $818; which is cheaper than the airline.
[11/18/2025 @ 08:36 PM] Price dropped to $334.
Delta has round-trip flights from Chicago (ORD) to Honolulu or Kona, Hawaii (HNL, KOA) for $362 with a connection. Flights January to March. Weekends available.
Image Credits: Mario Fajt, Creative Commons 2.0 (sobrecroacia.com)
Turkish Airlines has round-trip flights from Chicago (ORD) to Zagreb (ZAG) for $530-$569 with a connection. Flights January, February, March, April, May, and September. No weekend departures.
Some small OTAs on Skyscanner have this for as low as $530; which is cheaper than the airline.
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Air Canada has round-trip flights from Chicago (ORD) to Tokyo (NRT/HND) for $675-$681 with a connection. Flights November to December. Holiday blackouts.