TripVerdict

13 trips from Chicago come in under US$4,000 for a family of 4 at Christmas. The cheapest is Las Vegas, at about US$2,910.

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 5, 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. 1Las VegasUS$1,090 under budgetUS$2,910for 4 · all-in
  2. 2OrlandoUS$1,050 under budgetUS$2,950for 4 · all-in
  3. 3Washington DCUS$970 under budgetUS$3,030for 4 · all-in
  4. 4TampaUS$800 under budgetUS$3,200for 4 · all-in
  5. 5MiamiUS$730 under budgetUS$3,270for 4 · all-in
  6. 6Phoenix–ScottsdaleUS$610 under budget · checked Sep 28, 2026US$3,390for 4 · all-in
  7. 7TorontoUS$550 under budgetUS$3,450for 4 · all-in
  8. 8San DiegoUS$480 under budgetUS$3,520for 4 · all-in
  9. 9BostonUS$420 under budget · checked Oct 1, 2026US$3,580for 4 · all-in
  10. 10Los AngelesUS$330 under budgetUS$3,670for 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.

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The other 3, cheapest first

  1. 11New YorkUS$3,720checked Oct 8, 2026
  2. 12CancúnUS$3,830
  3. 13Los CabosUS$3,870

How far US$4,000 reaches

The dearest trips that still fit: Los Cabos (US$3,870), Cancún (US$3,830), New York (US$3,720).

Questions

Where can I go with US$4,000 for a family of 4 from Chicago?
13 of the 32 places we price come in under US$4,000 all-in at Christmas, from Las Vegas at about US$2,910 up to Los Cabos (US$3,870), Cancún (US$3,830), New York (US$3,720). That covers flights, 7 nights' stay, food and getting around.
What is the cheapest family vacation from Chicago at Christmas?
Las Vegas, at about US$2,910 all-in for a family of 4, then Orlando (US$2,950) and Washington DC (US$3,030). 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$1,520 (Las Vegas) all-in for 2 adults; half of the 13 places here come in under US$2,010.
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 5, 2026; your own dates are priced live when you open a trip. Ranked by price alone.

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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).