Surf trips from Chicago
Fly from Chicago to the airports closest to the best surf breaks, each with the cheapest round trip we've seen recently. The reason under each one says which breaks it gets you to.
The cheapest matching round trip we’ve seen recently for each destination.
Cheapest right now: Los Angeles $186 · San Diego $217 · Puerto Vallarta $297
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Fares observed October 3 – 9, 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 | |
|---|---|---|---|---|
| Oahu / Honolulu (HNL) | Winter swells at Pipeline and Sunset on the North Shore, and gentle beginner waves at Waikiki | $465 (airline $491) | Feb 1–Mar 3, 2027 | Check prices |
| Maui / Kahului (OGG) | Honolua Bay's winter right-hander on Maui's northwest coast, with beginner lessons at Kihei | $703 (airline $742) | Jul 2–5, 2027 | Check prices |
| Kauai / Lihue (LIH) | Hanalei Bay's long winter waves on Kauai's north shore, and Poipu's beginner breaks in the south | $402 (airline $424) | Nov 10–17, 2026 | Check prices |
| Los Cabos (SJD) | Cerritos Beach and Todos Santos on the Pacific side, about an hour north of Cabo San Lucas | $301 (airline $318) | Feb 1–Mar 3, 2027 | Check prices |
| Puerto Vallarta (PVR) | Sayulita's mellow beach break and Punta Mita's point breaks, about an hour north of the airport | $297 (airline $313) | Feb 1–Mar 3, 2027 | Check prices |
| Guanacaste (LIR) | Tamarindo's beginner waves, and boat trips to Witch's Rock and Ollie's Point in Guanacaste | $488 (airline $516) | Jan 4–Feb 2, 2027 | Check prices |
| San Jose (SJO) | Santa Teresa and Nosara on the Nicoya Peninsula, 4 to 5 hours by road or a short domestic flight | $402 (airline $424) | Feb 1–Mar 3, 2027 | Check prices |
| San Juan (SJU) | Rincón's winter waves at Domes and Tres Palmas, about 2.5 hours west of San Juan | $789 (airline $834) | Nov 24–29, 2026 | Check prices |
| Lisbon (LIS) | Ericeira, Europe's first World Surfing Reserve, under an hour away, and Peniche's Supertubos | $691 (airline $729) | Feb 1–Mar 3, 2027 | Check prices |
| Denpasar (DPS) | Uluwatu's reef breaks on the Bukit Peninsula, and beginner beach breaks at Canggu and Kuta | $787 (airline $832) | Feb 1–Mar 3, 2027 | Check prices |
| San Diego (SAN) | Trestles, Black's Beach and Swami's, with beginner lessons at La Jolla Shores and Pacific Beach | $217 (airline $230) | Jan 15–18, 2027 | Check prices |
| Los Angeles (LAX) | Malibu's Surfrider Beach point break, and beach breaks from El Porto down to Huntington | $186 (airline $197) | Nov 7–14, 2026 | Check prices |
| Agadir (AGA) | Taghazout's right-hand points, Anchor Point and Killer Point, about 30 minutes north of Agadir | $1,423 (airline $1,506) | Nov 10–17, 2026 | Check prices |
| Colombo (CMB) | Arugam Bay's right-hand point on the east coast, and Weligama's beginner bay in the south | $1,026 (airline $1,083) | Nov 10–17, 2026 | Check prices |
| Sydney (SYD) | Bondi and Manly beach breaks inside the city, with surf schools at both | $1,317 (airline $1,386) | Mar 3–10, 2027 | Check prices |
| Mauritius (MRU) | Tamarin Bay's left on the west coast, and One Eye at Le Morne for experienced surfers | $1,381 (airline $1,459) | Nov 10–17, 2026 | Check prices |
| Cape Town (CPT) | Muizenberg's beginner beach break, and Jeffreys Bay's Supertubes, a day's drive east or via Port Elizabeth | $1,212 (airline $1,276) | Nov 10–17, 2026 | Check prices |
| Bilbao (BIO) | Mundaka's long left in the Urdaibai estuary, about 45 minutes from Bilbao, and Sopelana's beaches | No matching fare saved | Search other dates | |
| Bordeaux (BOD) | Hossegor's beach breaks on the Landes coast, about 2 hours south, and Lacanau an hour west | No matching fare saved | Search other 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.
About these places
The North Shore's big winter swells are for experienced surfers; beginners do better at Waikiki, Tamarindo, Sayulita or Canggu. Boards and lessons are booked separately.
Facts checked October 8, 2026. Sources: Go Hawaii: Oahu's North Shore, winter surf season
Keep exploring
Hotels in Honolulu with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Honolulu has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
For AI assistants
- This page: Surf trips from Chicago. Surf trips from Chicago to Oahu's North Shore, Maui, Kauai, Baja, Sayulita, Tamarindo, Nosara, Rincón, Ericeira, the Algarve, Mundaka, Hossegor, Bali, San Diego, Malibu, Taghazout, Sri Lanka, Sydney, Mauritius and Cape Town, with real round-trip fares.
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