🌊 How to Get to Montauk From Chicago [2025–2026 Guide]

Fly Chicago to New York City in 2.5 hours ($150–$350), then take a 3-hour train, bus, or 2.5-hour drive to Montauk. Driving Chicago–Montauk takes 14–15 hours ($130–$180 fuel).

Montauk, the easternmost point of Long Island, New York, is known for its stunning beaches, state parks, and laid-back coastal vibe. Traveling from Chicago requires a combination of flight and local transport or a long scenic road trip. Here’s your complete 2025–2026 guide.

🛫 Flights From Chicago to Montauk

The fastest way is to fly to New York City, then connect to Montauk.

• Duration: Flights from Chicago O’Hare (ORD) or Midway (MDW) to New York City airports (JFK, LGA, or EWR) take 2.5–3 hours. From there, Montauk is another 120 miles east.

• Cost: Round-trip fares from Chicago to NYC range from $150–$350 depending on the season and booking time.

• Local Transfer: From NYC, you can drive (2.5–3 hours), take the Long Island Rail Road (LIRR) from Penn Station (3–3.5 hours), or ride a bus such as Hampton Jitney (3.5–4 hours).

• Pros & Cons: Fastest overall method; requires transfer from New York to Montauk.

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🚗 Driving From Chicago to Montauk

A long but flexible road trip.

• Distance & Time: About 950 miles, taking 14–15 hours without long stops.

• Route: Follow I-80 East through Indiana, Ohio, and Pennsylvania, then connect through New Jersey into Long Island.

• Cost: Fuel costs $130–$180 depending on vehicle; tolls can add $40–$60.

• Pros & Cons: Scenic Midwest and East Coast drive; flexibility with stops, but very time-consuming.

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🚆 Train + Bus Options

Public transport is possible with multiple connections.

• Train: Amtrak runs from Chicago to New York Penn Station (19–21 hours). From there, transfer to the Long Island Rail Road (LIRR) for a 3–3.5 hour ride to Montauk.

• Bus: Greyhound and Megabus operate Chicago to New York routes (15–17 hours). Once in NYC, connect with Hampton Jitney (3.5–4 hours) to Montauk.

• Cost: $100–$200 for long-distance plus $30–$60 for the NYC–Montauk segment.

• Pros & Cons: Economical and scenic; however, very long travel times.

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🚖 Local Transportation in Montauk

Once in Montauk, getting around is simple.

• Car Rentals: Available in NYC and Long Island; recommended for exploring beaches and parks.

• Taxis & Rideshares: Limited availability in Montauk; local taxis cost $10–$25 per short ride.

• Bikes: Popular way to explore town and nearby attractions; rentals average $25–$40/day.

• Walking: Downtown Montauk is compact and walkable, especially near the beach and restaurants.

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🌞 Best Time to Visit Montauk

Montauk is a seasonal destination with peak popularity in summer.

• Summer (June–August): Best for beaches, lively events, and warm weather; busiest and most expensive.

• Fall (September–October): Pleasant weather, lighter crowds, great for hiking and fishing.

• Winter (November–March): Quiet season, many businesses closed; peaceful coastal experience.

• Spring (April–May): Mild weather, blooming landscapes, fewer tourists, and lower prices.

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📝 Travel Summary Table

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❓ Frequently Asked Questions (FAQ)

Q1: How do I get to Montauk fastest from Chicago?
Fly to New York City (2.5–3 hours) and then drive, take the train, or bus 2.5–4 hours to Montauk.

Q2: Can I fly directly from Chicago to Montauk?
No, there are no direct flights. You must fly into New York City or Long Island.

Q3: How far is Montauk from New York City?
About 120 miles, or 2.5–3 hours by car.

Q4: Is it possible to drive from Chicago to Montauk?
Yes, but it’s a long trip of about 950 miles, taking 14–15 hours.

Q5: What is the best season to visit Montauk?
Summer for beaches and nightlife; fall for fewer crowds and great weather.

✅ This 2025–2026 Chicago-to-Montauk guide covers flights, train, bus, driving, and local travel tips for reaching Long Island’s famous seaside town.