TripVerdict

The cheapest spring break trip from Chicago is Los Cabos: about US$1,290 for 2, all-in.

Flights from Chicago, 7 nights' stay, food and getting around, for 2 adults, Mar 6–13, 2027.

All figures in US dollars (US$) · prices checked between Jul 26 and Nov 9, 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. 1Los Cabosfamily of 4: US$2,370–US$3,010 · checked Jul 26, 2026US$1,290for 2 · all-in
  2. 2Puerto Vallartafamily of 4: US$2,490–US$3,290 · checked Jul 26, 2026US$1,430for 2 · all-in
  3. 3Cancúnfamily of 4: US$2,680–US$3,600US$1,510for 2 · all-in
  4. 4Las Vegasfamily of 4: US$3,070–US$4,230US$1,710for 2 · all-in
  5. 5Punta Canafamily of 4: US$3,010–US$3,950 · checked Jul 26, 2026US$1,760for 2 · all-in
  6. 6Orlandofamily of 4: US$3,120–US$4,390 · checked Oct 6, 2026US$1,780for 2 · all-in
  7. 7Montego Bayfamily of 4: US$3,710–US$4,740 · checked Jul 26, 2026US$1,860for 2 · all-in
  8. 8Arubafamily of 4: US$3,870–US$4,980US$1,930for 2 · all-in
  9. 9Torontofamily of 4: US$3,370–US$4,650 · checked Jul 26, 2026US$1,950for 2 · all-in
  10. 10Tampafamily of 4: US$3,250–US$4,800 · checked Jul 26, 2026US$1,990for 2 · all-in

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The other 21, cheapest first

  1. 11BarbadosUS$2,170checked Jul 26, 2026
  2. 12Phoenix–ScottsdaleUS$2,220checked Jul 26, 2026
  3. 13Washington DCUS$2,250checked Jul 26, 2026
  4. 14Fort LauderdaleUS$2,260checked Jul 26, 2026
  5. 15BostonUS$2,270checked Jul 26, 2026
  6. 16New YorkUS$2,300
  7. 17Los AngelesUS$2,330checked Jul 26, 2026
  8. 18CuraçaoUS$2,350checked Jul 26, 2026
  9. 19AthensUS$2,380checked Jul 26, 2026
  10. 20Québec CityUS$2,480
  11. 21San DiegoUS$2,600checked Jul 26, 2026
  12. 22NassauUS$2,600
  13. 23LisbonUS$2,800checked Jul 26, 2026
  14. 24DublinUS$2,950checked Jul 26, 2026
  15. 25RomeUS$2,970
  16. 26BarcelonaUS$2,970checked Jul 26, 2026
  17. 27AmsterdamUS$3,260checked Jul 26, 2026
  18. 28HonoluluUS$3,260
  19. 29LondonUS$3,280
  20. 30ParisUS$3,290
  21. 31ReykjavíkUS$3,300checked Jul 26, 2026

Questions

What is the cheapest spring break trip from Chicago?
Los Cabos, at about US$1,290 all-in for 2, then Puerto Vallarta (US$1,430) and Cancún (US$1,510). Flights from Chicago, 7 nights' stay, food and getting around, for 2 adults, Mar 6–13, 2027.
How much is a spring break trip from Chicago for a family of 4?
From about US$2,370 (Los Cabos) all-in for 2 adults and 2 kids; half of the 31 places here come in under US$3,870.
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 Jul 26 and Nov 9, 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

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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).