How do I find cheap flights for backpacking?

Book 6-8 weeks in advance for the best prices, use open-jaw tickets (fly into one city, out of another) to avoid backtracking, and fly budget carriers for short hops. For transatlantic flights, departure city matters hugely — Boston is the closest US airport to Europe with fares from $280 to Reykjavik, while Miami is the cheapest gateway to Latin America. Set up Google Flights alerts and watch for flash sales from hub airports.

Philippe Murray-Pietsch

Discovery

Cheap Flights from Boston — The Closest US Airport to Europe

Bryan MendezJan 20266 min read

There is a reason budget transatlantic carriers keep adding Boston routes: geography. Logan is the closest major US airport to Europe. A flight to Reykjavik is 5 hours. Dublin is 6. Lisbon is 6.5. That is not much longer than flying domestic to LA. Shorter flights mean lower operating costs for airlines, which means cheaper tickets for you. PLAY regularly sells Boston to Reykjavik for under $300 round-trip. That is the price of a decent pair of hiking boots.

JetBlue's growing presence adds Caribbean muscle, and the Iceland stopover trick lets you see two destinations for the price of one flight. Boston punches way above its weight for budget international travel.

The Airport Situation

BOS (Logan) — Everything runs through here. Terminal E for international, Terminal C for JetBlue. Blue Line subway to downtown costs $2.40 and takes 15 minutes. Free shuttle between terminals. There is a water taxi option for $15 if you want to feel fancy.

Skip the Uber. The Blue Line is fast, cheap, and does not require sitting in the Ted Williams Tunnel for 45 minutes.

Worth knowing about nearby alternatives — Providence (PVD) is an hour south, Manchester (MHT) an hour north, Hartford (BDL) 1.5 hours west. All sometimes have cheaper fares on budget carriers and are worth a quick search.

Boston to Europe — Your Geographic Superpower

What You Should Expect to Pay (Round-Trip)

Reykjavik: $250-400 — PLAY / Icelandair — 5h
Dublin: $320-450 — Aer Lingus — 6h
London: $380-520 — JetBlue / Norse — 6.5h
Lisbon: $350-480 — TAP Portugal — 6.5h
Paris: $400-550 — JetBlue / Delta — 7h
Amsterdam: $420-580 — Delta / KLM — 7h

The Airlines Worth Knowing

PLAY — Ultra-low-cost to Reykjavik, often under $300 round-trip. Use Iceland as a free stopover to break up the journey. Bare-bones service, but the price is the point.

Icelandair — Slightly more polish than PLAY, same Reykjavik routing. Free stopover for up to 7 days. Better connections to Scandinavia.

TAP Portugal — Lisbon is often the cheapest European gateway from Boston. Their stopover program gives you free time in Portugal. Easy connections to everywhere via Lisbon.

JetBlue — Growing transatlantic presence. London and Paris direct. TrueBlue points are easy to earn and actually useful. Mint class is reasonable if you ever want to splurge.

Aer Lingus — Direct to Dublin with US preclearance, meaning you skip immigration when you land back home. Worth something on a red-eye return.

Norse Atlantic — Took over Norwegian's London Gatwick routes. Competitive pricing if you book early.

Sample Itineraries

Iceland + Europe (2 weeks) — BOS to Reykjavik ($280 on PLAY). Three days in Iceland. Reykjavik to London ($100 on PLAY). Train to Paris. Return from Paris on JetBlue ($450). Total flights around $700.

Portugal + Spain (2 weeks) — BOS to Lisbon ($380 on TAP with stopover). Porto, Madrid, Barcelona. Open jaw return from Barcelona ($420). Total flights around $600.

Boston to the Caribbean — JetBlue Territory

JetBlue makes Boston a legitimate Caribbean gateway:

San Juan: $180-280 — 3.5h
Cancun: $250-380 — 4.5h
Punta Cana: $300-420 — 4h
Nassau: $280-400 — 3h
Aruba: $350-480 — 5h

JetBlue's Blue Basic fares to San Juan can drop to $150 round-trip during sales. That is a long weekend in Puerto Rico for the price of a nice dinner in Back Bay.

Sample Itinerary

Caribbean Hop (10 days) — BOS to San Juan ($180 on JetBlue). Cape Air to St. Thomas ($80). Ferry to Tortola. Return from San Juan ($140). Total flights around $400.

Boston to Latin America — Connection Game

Fewer direct options, but workable:

Mexico City: $350-500 — BOS-MEX direct — 5.5h
Bogota: $400-550 — BOS-MIA-BOG — 9h
Lima: $500-700 — BOS-MIA-LIM — 12h
Sao Paulo: $650-850 — BOS-JFK-GRU — 14h

Connect through JFK or Miami for better Latin America options. The positioning flight adds time but usually saves money versus direct fares from Logan.

Boston to Asia — Through the Middle East

Boston's Asia options have improved, but they still require connections:

Tokyo: $700-900 — BOS-NRT direct (JAL) — 14h
Bangkok: $700-900 — BOS-DOH-BKK (Qatar) — 20h
Seoul: $800-1000 — BOS-ICN via Tokyo — 18h
Hong Kong: $750-950 — BOS-NRT-HKG — 19h

Japan Airlines flies Boston to Tokyo with excellent service. Qatar through Doha is the best value to Southeast Asia — the Doha hub connects to everywhere.

Sample Itinerary

Asia via Middle East (3 weeks) — BOS to Bangkok ($700 via Doha on Qatar). Thailand to Vietnam ($80 on AirAsia). Return from Ho Chi Minh City via Doha ($600). Total flights around $1,100.

Boston-Specific Moves

The Iceland stopover — PLAY and Icelandair both offer cheap Boston to Reykjavik. Use Iceland as a free multi-day stopover, then connect onward to Europe. You see two countries for the price of one flight.

TAP's Lisbon strategy — Lisbon is often cheapest European gateway from BOS. TAP's stopover program is free. Easy Ryanair or TAP connections to all of Europe from there.

Book timing — Europe cheapest January through March and October through November, book 2-4 months ahead. Caribbean cheapest May through June and September through November, book 1-2 months ahead. Asia cheapest January through March, book 3-5 months ahead.