Flights from Chicago to the Caribbean for spring break
March is dry, warm and busy across the Caribbean. Punta Cana, Montego Bay and Nassau have the most nonstops and the most spring-break crowds; Aruba, Curaçao and the smaller islands are the same weather with a calmer week.
Nonstop from Chicago: Punta Cana (4h 34m), Montego Bay (4h 07m), Nassau (United, American), Aruba (5h 12m), San Juan (4h 37m), Grand Cayman Island (American, United), Saint Thomas (United, American), Sint Maarten (American, United), Curacao (American) and Saint Lucia (United). No nonstop seen to Bridgetown, Antigua, Kingston, Santo Domingo and Saint Croix on the dates searched recently. No recent searches for Providenciales.
Axel's pick: San Juan, nonstop and the lowest fare saved for these dates, $481.
Where to fly from Chicago to the Caribbean for spring break: fares for Spring break, week of March 13 (Mar 13 to 20) and Spring break, week of March 20 (Mar 20 to 27) 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.
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Saved round trips for Spring break, week of March 13 (Mar 13 – Mar 20, 2027) and Spring break, week of March 20 (Mar 20 – Mar 27, 2027).
Cheapest right now: San Juan $481 · Nassau $671 · Montego Bay $775
Fares observed October 23 – 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.
| Destination | Why go | Flights | Axel | Dates | |
|---|---|---|---|---|---|
| Punta Cana (PUJ) | Punta Cana's long white-sand beaches and all-inclusive resorts | Nonstop · 4h 34m | $1,557 (airline $1,641) · 2 adults | Mar 13–20, 2027 | Check prices |
| Montego Bay (MBJ) | Jamaica's resort coast around Montego Bay and Negril | Nonstop · 4h 07m | $775 (airline $818) | Mar 13–20, 2027 | Check prices |
| Nassau (NAS) | Nassau and Paradise Island, a short flight from the East Coast | Nonstop · United, American | $671 (airline $708) | Mar 13–20, 2027 | Check prices |
| Aruba (AUA) | Aruba's dry, sunny weather outside the hurricane belt | Nonstop · 5h 12m | $817 (airline $861) | Mar 13–20, 2027 | Check prices |
| San Juan (SJU) | Old San Juan, beaches and the rainforest, no passport needed from the US | Nonstop · 4h 37m | $481 (airline $506) | Mar 13–20, 2027 | Check prices |
| Grand Cayman Island (GCM) | Seven Mile Beach and world-class diving on Grand Cayman | Nonstop · American, United | No matching fare saved | Mar 13 – Mar 20, 2027 (suggested) | Search these dates |
| Providenciales (PLS) | Grace Bay in Turks and Caicos, one of the Caribbean's best-known beaches | No matching fare saved | Mar 13 – Mar 20, 2027 (suggested) | Search these dates | |
| Saint Thomas (STT) | St. Thomas beaches and an easy ferry to St. John, no passport needed from the US | Nonstop · United, American | No matching fare saved | Mar 13 – Mar 20, 2027 (suggested) | Search these dates |
| Sint Maarten (SXM) | St. Martin, two countries on one island with plenty of beaches | Nonstop · American, United | No matching fare saved | Mar 13 – Mar 20, 2027 (suggested) | Search these dates |
| Curacao (CUR) | Curaçao's calm coves for snorkelling and colourful Willemstad | Nonstop · American | No matching fare saved | Mar 13 – Mar 20, 2027 (suggested) | Search these dates |
| Bridgetown (BGI) | Barbados beaches on the calm west coast and surf on the east | No nonstop seen | No matching fare saved | Mar 13 – Mar 20, 2027 (suggested) | Search these dates |
| Saint Lucia (UVF) | St. Lucia's Pitons, rainforest and resort beaches | Nonstop · United | No matching fare saved | Mar 13 – Mar 20, 2027 (suggested) | Search these dates |
| Antigua (ANU) | Antigua, a beach for every day of the year | No nonstop seen | No matching fare saved | Mar 13 – Mar 20, 2027 (suggested) | Search these dates |
| Kingston (KIN) | Kingston, Jamaica's capital, with the Blue Mountains nearby | No nonstop seen | No matching fare saved | Mar 13 – Mar 20, 2027 (suggested) | Search these dates |
| Santo Domingo (SDQ) | Santo Domingo's colonial zone, the oldest city in the Americas | No nonstop seen | No matching fare saved | Mar 13 – Mar 20, 2027 (suggested) | Search these dates |
| Saint Croix (STX) | St. Croix's beaches, rum distilleries and Danish-era towns, no passport needed from the US | No nonstop seen | No matching fare saved | Mar 13 – Mar 20, 2027 (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.
Keep exploring
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 spring break. Round-trip fares from Chicago to the Caribbean for spring break: Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more, priced for Spring break, week of March 13 (Mar 13 to 20) and Spring break, week of March 20 (Mar 20 to 27). 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.