Beach vacations from Chicago
The best beach trips you can fly to from Chicago, each with the cheapest round trip we've seen recently. Pick one to see every date, or check your own dates in one tap.
The cheapest matching round trip we’ve seen recently for each destination.
Cheapest right now: Fort Lauderdale $169 · Miami $185 · San Juan $282
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Fares observed October 9 – 15, 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 | Axel | Dates | |
|---|---|---|---|---|
| Cancun (CUN) | Caribbean beaches and the Hotel Zone, with Tulum and Playa del Carmen an hour or two south | $286 (airline $302) | Feb 1–Mar 3, 2027 | Check prices |
| Punta Cana (PUJ) | Long white-sand beaches and easy all-inclusive resorts | $599 (airline $633) | Mar 13–20, 2027 | Check prices |
| Aruba (AUA) | Dry, sunny and outside the hurricane belt, so it is a safe bet most of the year | $670 (airline $706) | Mar 13–20, 2027 | Check prices |
| Montego Bay (MBJ) | Jamaica's resort coast around Montego Bay and Negril | from $461 (airline $486) | Oct 29–Nov 5, 2026 | Check prices |
| Nassau (NAS) | Nassau and Paradise Island, a short flight from the East Coast | $581 (airline $615) | Jan 15–18, 2027 | Check prices |
| Providenciales (PLS) | Grace Bay in Turks and Caicos, one of the Caribbean's best-known beaches | from $838 (airline $884) | Oct 27–Nov 3, 2026 | Check prices |
| Grand Cayman Island (GCM) | Seven Mile Beach and world-class diving in Grand Cayman | No matching fare saved | Search other dates | |
| San Juan (SJU) | Old San Juan, beaches and the rainforest, with no passport needed from the US | $282 (airline $297) | Oct 20–27, 2026 | Check prices |
| Saint Thomas (STT) | St. Thomas beaches and an easy ferry to St. John, no passport needed from the US | No matching fare saved | Search other dates | |
| Curacao (CUR) | Calm coves for snorkelling and a colourful capital, Willemstad | No matching fare saved | Search other dates | |
| Bridgetown (BGI) | Barbados beaches on the calm west coast and surf on the east | No matching fare saved | Search other dates | |
| Saint Lucia (UVF) | St. Lucia's Pitons, rainforest and quiet bays | $784 (airline $826) | Feb 12–15, 2027 | Check prices |
| Antigua (ANU) | Antigua, known for having a beach for every day of the year | No matching fare saved | Search other dates | |
| Sint Maarten (SXM) | St. Martin, two countries on one island with plenty of beaches | $963 (airline $1,015) · 2 adults | Jan 16–23, 2027 | Check prices |
| Puerto Vallarta (PVR) | Puerto Vallarta's Pacific beaches and a walkable old town | $297 (airline $313) | Feb 1–Mar 3, 2027 | Check prices |
| Los Cabos (SJD) | Los Cabos, desert coast, resorts and whale watching in winter | $301 (airline $318) | Feb 1–Mar 3, 2027 | Check prices |
| TULUM (TQO) | Tulum's own airport, close to the beaches and the Mayan ruins | $788 (airline $833) | Feb 12–15, 2027 | Check prices |
| Guanacaste (LIR) | Guanacaste's Pacific beaches in Costa Rica | $488 (airline $516) | Jan 4–Feb 2, 2027 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki and the North Shore on Oahu | $464 (airline $490) | Jan 4–Feb 2, 2027 | Check prices |
| Maui / Kahului (OGG) | Maui's beaches, the Road to Hana and Haleakalā | $763 (airline $804) | Aug 7–14, 2027 | Check prices |
| Big Island / Kona (KOA) | The Big Island's Kona coast, volcanoes and snorkelling | $601 (airline $636) | Jan 4–Feb 2, 2027 | Check prices |
| Kauai / Lihue (LIH) | Kauai, the Garden Isle, with the Nā Pali coast | $527 (airline $557) | Feb 12–16, 2027 | Check prices |
| Miami (MIA) | Miami Beach, warm water and a big food and nightlife scene | $185 (airline $196) | Dec 3–7, 2026 | Check prices |
| Fort Lauderdale (FLL) | Fort Lauderdale beaches and an easy base for cruises | $169 (airline $178) | Jan 8–10, 2027 | Check prices |
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 Cancun with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Cancun has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
For AI assistants
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