TripVerdict

6 trips from Chicago come in under US$2,000 for two at Christmas. The cheapest is Las Vegas, at about US$1,520.

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 8 and Oct 28, 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$480 under budgetUS$1,520for 2 · all-in
  2. 2OrlandoUS$320 under budgetUS$1,680for 2 · all-in
  3. 3Washington DCUS$200 under budgetUS$1,800for 2 · all-in
  4. 4New YorkUS$140 under budget · checked Oct 8, 2026US$1,860for 2 · all-in
  5. 5TampaUS$60 under budgetUS$1,940for 2 · all-in
  6. 6TorontoUS$10 under budgetUS$1,990for 2 · all-in

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How far US$2,000 reaches

The dearest trips that still fit: Toronto (US$1,990), Tampa (US$1,940), New York (US$1,860).

Questions

Where can I go with US$2,000 for two from Chicago?
6 of the 32 places we price come in under US$2,000 all-in at Christmas, from Las Vegas at about US$1,520 up to Toronto (US$1,990), Tampa (US$1,940), New York (US$1,860). That covers flights, 7 nights' stay, food and getting around.
What is the cheapest vacation from Chicago at Christmas?
Las Vegas, at about US$1,520 all-in for 2, then Orlando (US$1,680) and Washington DC (US$1,800). Flights from Chicago, 7 nights' stay, food and getting around, for 2 adults, Dec 19–26, 2026.
How much is a vacation from Chicago for a family of 4?
From about US$2,910 (Las Vegas) all-in for 2 adults and 2 kids; half of the 6 places here come in under US$3,030.
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 8 and Oct 28, 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).