TripVerdict

The cheapest Christmas trip from Chicago is Las Vegas: about US$1,520 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 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 Vegasfamily of 4: US$2,910–US$3,860US$1,520for 2 · all-in
  2. 2Orlandofamily of 4: US$2,950–US$4,180US$1,680for 2 · all-in
  3. 3Washington DCfamily of 4: US$3,030–US$4,130US$1,800for 2 · all-in
  4. 4New Yorkfamily of 4: US$3,720–US$5,380 · checked Oct 8, 2026US$1,860for 2 · all-in
  5. 5Tampafamily of 4: US$3,200–US$4,500US$1,940for 2 · all-in
  6. 6Torontofamily of 4: US$3,450–US$4,730US$1,990for 2 · all-in
  7. 7Phoenix–Scottsdalefamily of 4: US$3,390–US$4,670 · checked Sep 28, 2026US$2,010for 2 · all-in
  8. 8Los Cabosfamily of 4: US$3,870–US$4,540US$2,030for 2 · all-in
  9. 9Miamifamily of 4: US$3,270–US$4,770US$2,080for 2 · all-in
  10. 10Cancúnfamily of 4: US$3,830–US$4,760US$2,090for 2 · all-in

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The other 22, 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
  18. 28LondonUS$4,200
  19. 29RomeUS$4,260
  20. 30AthensUS$4,270
  21. 31BarcelonaUS$4,270
  22. 32AmsterdamUS$4,560checked Oct 12, 2026

Questions

What is the cheapest Christmas trip from Chicago?
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 Christmas trip 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 32 places here come in under US$4,240.
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.

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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).