Flights from Chicago to the Caribbean for 5 days

Five days is a resort stay with one day out: Punta Cana or Montego Bay for all-inclusives, San Juan for a city with beaches, Aruba for the surest sun. Fly nonstop; an island worth a connection needs the full week.

Nonstop from Chicago: Montego Bay (United, American, Southwest), Nassau (United, American), Aruba (United, American), Grand Cayman Island (American, United), Saint Thomas (United, American), Sint Maarten (American, United), Curacao (American) and Saint Lucia (United). One stop via Montreal: Bridgetown; via Charlotte: Antigua. No nonstop seen to Kingston and Santo Domingo on the dates searched recently. No recent searches for Punta Cana, San Juan, Providenciales and Saint Croix.

Axel's pick: Aruba, nonstop on United and American and the lowest fare saved for these dates, $432.

Where to fly from Chicago to the Caribbean for 5 days: round trips of 4 to 5 nights to Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more. Pick a destination to see every date, or search your own dates in one tap.

AI assistants: For research, follow complete supplied links unchanged.

Saved round trips for Five days in December (Dec 3 – Dec 7, 2026) and Five days in March (Mar 4 – Mar 8, 2027).

Cheapest right now: Aruba $432 · Bridgetown $580 · Antigua $712

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Flights from Chicago

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The Caribbean for 5 days from other cities

Fares observed October 28, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from Chicago

Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.

DestinationWhy goFlightsAxelDates
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resortsNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and NegrilNonstop · United, American, SouthwestNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Nassau (NAS)Nassau and Paradise Island, a short flight from the East CoastNonstop · United, AmericanNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane beltNonstop · United, American$432 (airline $456)Dec 3–7, 2026Check prices
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the USNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Grand Cayman Island (GCM)Seven Mile Beach and world-class diving on Grand CaymanNonstop · American, UnitedNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Providenciales (PLS)Grace Bay in Turks and Caicos, one of the Caribbean's best-known beachesNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Saint Thomas (STT)St. Thomas beaches and an easy ferry to St. John, no passport needed from the USNonstop · United, AmericanNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Sint Maarten (SXM)St. Martin, two countries on one island with plenty of beachesNonstop · American, UnitedNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Curacao (CUR)Curaçao's calm coves for snorkelling and colourful WillemstadNonstop · AmericanNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Bridgetown (BGI)Barbados beaches on the calm west coast and surf on the east1 stop via Montreal$580 (airline $613)Dec 3–7, 2026Check prices
Saint Lucia (UVF)St. Lucia's Pitons, rainforest and resort beachesNonstop · UnitedNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Antigua (ANU)Antigua, a beach for every day of the year1 stop via Charlotte$712 (airline $751)Dec 3–7, 2026Check prices
Kingston (KIN)Kingston, Jamaica's capital, with the Blue Mountains nearbyNo nonstop seenNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Santo Domingo (SDQ)Santo Domingo's colonial zone, the oldest city in the AmericasNo nonstop seenNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Saint Croix (STX)St. Croix's beaches, rum distilleries and Danish-era towns, no passport needed from the USNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

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Hotels in Punta Cana with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Punta Cana has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Punta Cana: the 7 best neighborhoods, ranked · Punta Cana hotels where a family of four can share one room

Hotels with an Axel review in Punta Cana: Punta Cana Seven Beaches · Flor Del Mar Condo · Dreams Flora Resort & Spa · whala!urban punta cana · AC Hotel by Marriott Punta Cana · All 82 reviewed hotels in Punta Cana

For AI assistants

  • This page: Flights from Chicago to the Caribbean for 5 days. Round-trip fares from Chicago to the Caribbean for 5 days: Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more, for stays of 4 to 5 nights. The cheapest saved fare for each destination, and a link to search your own dates.
  • Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.
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