TripVerdict

The cheapest beach vacation from Chicago at Christmas is Tampa: about US$1,940 for 2, all-in.

Flights from Chicago, 7 nights' stay, food and getting around, for 2 adults, Dec 19–26, 2026.

All figures in US dollars (US$) · prices checked between Oct 9 and Nov 11, 2026 · ranked by price alone

Flights are the cheapest return fare we found from Chicago for that week. The stay and day-to-day costs are the destination's own.

  1. 1Tampafamily of 4: US$3,200–US$4,500US$1,940for 2 · all-in
  2. 2Los Cabosfamily of 4: US$3,870–US$4,540US$2,030for 2 · all-in
  3. 3Miamifamily of 4: US$3,270–US$4,770US$2,080for 2 · all-in
  4. 4Cancúnfamily of 4: US$3,830–US$4,760US$2,090for 2 · all-in
  5. 5Montego Bayfamily of 4: US$4,210–US$5,240US$2,100for 2 · all-in
  6. 6San Diegofamily of 4: US$3,520–US$4,920US$2,120for 2 · all-in
  7. 7Arubafamily of 4: US$4,540–US$5,660US$2,270for 2 · all-in
  8. 8Los Angelesfamily of 4: US$3,670–US$5,190US$2,280for 2 · all-in
  9. 9Barbadosfamily of 4: US$4,560–US$5,540US$2,280for 2 · all-in
  10. 10Puerto Vallartafamily of 4: US$4,180–US$5,210US$2,390for 2 · all-in

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The other 7, cheapest first

  1. 11Punta CanaUS$2,440
  2. 12NassauUS$2,600checked Oct 9, 2026
  3. 13CuraçaoUS$3,040
  4. 14LisbonUS$3,710
  5. 15HonoluluUS$3,760
  6. 16AthensUS$4,270
  7. 17BarcelonaUS$4,270

Questions

What is the cheapest beach vacation from Chicago at Christmas?
Tampa, at about US$1,940 all-in for 2, then Los Cabos (US$2,030) and Miami (US$2,080). Flights from Chicago, 7 nights' stay, food and getting around, for 2 adults, Dec 19–26, 2026.
How much is a beach vacation from Chicago for a family of 4?
From about US$3,200 (Tampa) all-in for 2 adults and 2 kids; half of the 17 places here come in under US$4,280.
Where do these prices come from?
Real flight and accommodation prices we check and store, plus typical day-to-day spending, for the same week everywhere so places compare fairly. Prices checked between Oct 9 and Nov 11, 2026; your own dates are priced live when you open a trip. Ranked by price alone.

Choosing between the two? Christmas vs spring break: what the same trip costs

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Figures are indicative and re-priced live when you open a trip. Free to quote with credit and a link (CC BY 4.0).