TripVerdict

The cheapest family vacation from Chicago at Christmas is Orlando: about US$2,950 for a family of 4, all-in.

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

All figures in US dollars (US$) · prices checked between Sep 28 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. 1Orlandofor 2: from US$1,680US$2,950for 4 · all-in
  2. 2Washington DCfor 2: from US$1,800US$3,030for 4 · all-in
  3. 3Tampafor 2: from US$1,940US$3,200for 4 · all-in
  4. 4Phoenix–Scottsdalefor 2: from US$2,010 · checked Sep 28, 2026US$3,390for 4 · all-in
  5. 5San Diegofor 2: from US$2,120US$3,520for 4 · all-in
  6. 6Bostonfor 2: from US$2,210 · checked Oct 1, 2026US$3,580for 4 · all-in
  7. 7Cancúnfor 2: from US$2,090US$3,830for 4 · all-in
  8. 8Los Cabosfor 2: from US$2,030US$3,870for 4 · all-in
  9. 9Puerto Vallartafor 2: from US$2,390US$4,180for 4 · all-in
  10. 10Nassaufor 2: from US$2,600 · checked Oct 9, 2026US$4,280for 4 · all-in

Your dates, your party, your city

Open any place above to change the dates and who's going, or tell us the whole trip and we'll price it live.

Price my trip →

The other 6, cheapest first

  1. 11Punta CanaUS$4,390
  2. 12ArubaUS$4,540
  3. 13BarbadosUS$4,560
  4. 14Québec CityUS$5,360
  5. 15DublinUS$6,830
  6. 16AmsterdamUS$9,120checked Oct 12, 2026

Questions

What is the cheapest family vacation from Chicago at Christmas?
Orlando, at about US$2,950 all-in for a family of 4, then Washington DC (US$3,030) and Tampa (US$3,200). Flights from Chicago, 7 nights' stay, food and getting around, for 2 adults and 2 kids, Dec 19–26, 2026.
How much is a family vacation from Chicago for 2?
From about US$1,680 (Orlando) all-in for 2 adults; half of the 16 places here come in under US$2,210.
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 Sep 28 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

More cheapest-first lists

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