TripVerdict

27 trips from Chicago come in under US$4,000 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 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. 1Las VegasUS$2,480 under budgetUS$1,520for 2 · all-in
  2. 2OrlandoUS$2,320 under budgetUS$1,680for 2 · all-in
  3. 3Washington DCUS$2,200 under budgetUS$1,800for 2 · all-in
  4. 4New YorkUS$2,140 under budget · checked Oct 8, 2026US$1,860for 2 · all-in
  5. 5TampaUS$2,060 under budgetUS$1,940for 2 · all-in
  6. 6TorontoUS$2,010 under budgetUS$1,990for 2 · all-in
  7. 7Phoenix–ScottsdaleUS$1,990 under budget · checked Sep 28, 2026US$2,010for 2 · all-in
  8. 8Los CabosUS$1,970 under budgetUS$2,030for 2 · all-in
  9. 9MiamiUS$1,920 under budgetUS$2,080for 2 · all-in
  10. 10CancúnUS$1,910 under budgetUS$2,090for 2 · all-in

Your dates, your party, your city

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The other 17, cheapest first

  1. 11Montego BayUS$2,100
  2. 12San DiegoUS$2,120
  3. 13BostonUS$2,210checked Oct 1, 2026
  4. 14ArubaUS$2,270
  5. 15Los AngelesUS$2,280
  6. 16BarbadosUS$2,280
  7. 17Mexico CityUS$2,300
  8. 18Puerto VallartaUS$2,390
  9. 19Punta CanaUS$2,440
  10. 20NassauUS$2,600checked Oct 9, 2026
  11. 21Québec CityUS$2,990
  12. 22CuraçaoUS$3,040
  13. 23LisbonUS$3,710
  14. 24HonoluluUS$3,760
  15. 25DublinUS$3,850
  16. 26ReykjavíkUS$3,910
  17. 27ParisUS$3,990

How far US$4,000 reaches

The dearest trips that still fit: Paris (US$3,990), Reykjavík (US$3,910), Dublin (US$3,850).

Questions

Where can I go with US$4,000 for two from Chicago?
27 of the 32 places we price come in under US$4,000 all-in at Christmas, from Las Vegas at about US$1,520 up to Paris (US$3,990), Reykjavík (US$3,910), Dublin (US$3,850). 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 27 places here come in under US$4,180.
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).