Costa Rica is great and fits the criteria you mention. Not sure about flights from Chicago; you’d have to check on that.

St. Martin? I’m not sure if they have a direct flight from Chicago, but you probably could fly into San Juan and get a flight from there.

Cool place. I went there during Christmas week of my freshman year of college, and I had a great time.

I second Costa Rice. Close (for me) and cheep.

Puerto Rico. It has the exotic island setting, but is run under American laws so it’s much safer than Mexico is these days.

Anywhere in the Caribbean. Grand Cayman is nice,

Try Santa Barbara. It’s warm, the food is good and there are lots of things to do there. Plus, it’s beautiful there!

Cancun is beautiful.

My living room. Always a cozy 70ish degrees with wool persian rugs, cats and sunny windows. lol

Yesss! @Coloma ‘s for the winter!

@ChazMaz A little too enthusiastic aren’t you?

Palm Springs is great. but I’d go to Maui!

San Diego. I lived there for 13 years and still vacation there in the winter. Plenty to do & see, plus near L.A. Phoenix is less so, but still reliably warm. There’s always Las Vegas, especially if you don’t gamble. There are plenty of good “sunbelt” cities in southwestern U.S. that stay reasonably warm in the winter.

Puerto Rico doesn’t require passports. You could tour El Yunque rainforest which has wonderful waterfalls, swim in the biophosphoresence at Vieques with a tour, go dancing, tour the architecture or art museums or lay on the beach and bake.

Honolulu, central america, carribbean, puerto rico, south pacific. Essentially any place along or near to the equator. 3–4 days isn’t very much. Pick somewhere near with little to no time difference to minimize travel and recovery time. Maybe try Bermuda.

Turks and Caicos

Ok, so we can’t say what suggestions suck can we? ;-)

When my husband and I went to the west coast of Mexico we were in San Diego for a layover. I loved that city and want to go back when we get a chance.

A good destination for Christmas vacation is Naples, Florida. Naples is located in Southwest Florida, on the shores of the Gulf of Mexico.
Naples climate is mild year round and gets lots of sunshine hours. Although this area is very upscale, you can find quite reasonable priced accommodations too. There’s beach front resorts and lots of hotels and condos to choose from away from the beach too. Vacation rentals are also very popular in Naples.
There is plenty to do for families and couples. The gorgeous white sand beaches are the main focus of the area. There are lots of restaurants in a variety of price ranges, too.
Naples is known to be a very safe area too, which is important when travelling.