Delta has round-trip flights from Houston (HOU/IAH) to Tokyo (HND) for $898-$904 with a connection. Flights January to February. Departures on Monday, Tuesday, Wednesday, Saturday, and Sunday. 7-day minimum stay required.
Downside: Tokyo winters are very cold.
Upside: A round-trip ticket from Tokyo to Okinawa is about $120-$170 on JetStar and ANA.
JetBlue has round-trip flights from Houston (IAH) to Nassau, Bahamas (NAS) for $329-$334 with a connection. Flights August, September, October, and December. Departures on Monday, Tuesday, Wednesday, Saturday, and Sunday. Origin/Destination reversible. No Christmas dates available.
United has round-trip flights from Houston (IAH) to Liberia, Costa Rica (LIR) for $366, NONSTOP. Flights August to December. Departures on Monday, Tuesday, Wednesday, and Sunday. Origin/Destination reversible. No Christmas dates available.
Southwest and United have round-trip flights from Houston (HOU/IAH) to San Francisco, Pensacola, or Panama City Florida (SFO, ECP, PNS) for $166-$245, NONSTOP. Flights August to December. No Sunday departures. A few weekends available (mostly Saturdays). Origin/Destination reversible. No Christmas dates available.
American and Delta have beaten the Southwest Hawaii fare sale to Kona and Maui.
Round-trip flights from Houston (IAH) to Kailua-Kona or Maui, Hawaii (KOA, OGG) are now $344-$380 with a connection. Flights in August, November, and December. Departures on Monday, Tuesday, Wednesday, and Sunday. Origin/Destination reversible. Holiday blackouts.
Southwest has round-trip flights from Houston (HOU) to Colorado Springs (COS) for $179-$218, NONSTOP. Flights August to December. No weekend departures. Origin/Destination reversible. No Christmas dates available.
Southwest has round-trip flights from Houston (HOU) to San Jose, Costa Rica (SJO) for $379, NONSTOP. Flights August to December. Departures on Monday, Tuesday, Wednesday, and Sunday. Origin/Destination reversible. No Christmas dates available.
JetBlue and Southwest have round-trip flights from Houston (IAH) to Sint Maarten (SXM) for $365-$389 with a connection. Flights August to October. Very few weekends available. Origin/Destination reversible.
Most availability is in September.
Updated: [06/08/2026 @ 12:12 PM CT] American has beaten the Southwest sale with $344-$380 round-trip flights to Maui/Kona.
Southwest and American have round-trip flights from Houston (HOU) to Honolulu, Maui, Kauai-Lihue, or Kona, Hawaii (HNL, OGG, LIH, KOA) for $344-$404 with a connection. Origin/Destination reversible. No Thanksgiving dates.
Honolulu flights September and November. Very limited.
Maui flights August, October, November, and December. Lots of availability.
Kauai flights August to December.
Kona flights October to November. Very limited. Use link list.
JetBlue has round-trip flights from Houston (IAH) to Montego Bay (MBJ) for $303-$322 with a connection. Flights in September, November, and December. Origin/Destination reversible. Holiday blackouts.
American Airlines and United have round-trip flights from Houston (IAH) to Kailua-Kona or Lihue, Hawaii (KOA, LIH) for $344-$380 with a connection. Flights August to September. Origin/Destination reversible.
Delta has round-trip flights from Houston (IAH) to Kahului-Maui, Hawaii (OGG) for $344 with a connection. Flights August to September. Departures on Wednesday and Sunday. Origin/Destination reversible.
Limited calendar availability. See updated link list on our website for a list of every date that we’ve found to work with this, so far.
Delta has round-trip flights from Houston (HOU/IAH) to Destin, Florida (VPS) for $191-$216 with a connection. Flights August to September. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Origin/Destination reversible.
ZIPAIR Tokyo has round-trip flights from Houston (IAH) to Tokyo (NRT) for $607-$648, NONSTOP. Flights August to September.
United and Southwest have round-trip flights from Houston (IAH/HOU) to Nashville (BNA) for $189, NONSTOP. Flights May to November. Departures on Tuesday and Wednesday. Origin/Destination reversible. No Thanksgiving dates.
Delta has round-trip flights from Houston (IAH) to Atlanta (ATL) for $117, NONSTOP. Flights June to August. Departures on Tuesday, Wednesday, and Saturday. Origin/Destination reversible.
WestJet has round-trip flights from Houston (IAH) to Vancouver or Edmonton (YVR, YEG) for $299-$329 with a connection. Vancouver flights July to December. Edmonton flights October to November. Weekends available. Origin/Destination reversible. No Christmas dates available.
Delta has round-trip flights from Houston (HOU/IAH) to Saint Thomas (STT) for $250 with a connection. Flights August, September, December, January, and February. Departures on Monday, Tuesday, Thursday, Saturday, and Sunday. Origin/Destination reversible. No Christmas dates available.
American Airlines has round-trip flights from Houston (IAH/HOU) to San Francisco (SFO) for $221-$241 with a connection. Flights July to December. No discounted Monday departures. Cheapest departures are on Tuesdays, Wednesdays, and Saturdays. Origin/Destination reversible. No Christmas dates available.
There is only one Friday departure date; Sep – 11.
JetBlue has round-trip flights from Houston (IAH) to Medellin, Colombia (MDE) for $380-$499 with a connection. Flights July to August. Origin/Destination reversible.
Cheapest date found was only on this date pair: Aug 16 – Aug 22. Other dates are more expensive in the price range.
