How to Get to Montauk From Chicago [2026-2027 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 2026 guide.

🛫 Flights From Chicago to Montauk

Planning a trip from Chicago to Montauk requires flying into a New York City airport before making the final trek east to the Hamptons. Because Montauk does not have its own commercial airport, the fastest and most efficient travel route is to catch a direct flight from Chicago O’Hare (ORD) or Chicago Midway (MDW) to one of the major NYC hub airports, including JFK, LaGuardia (LGA), or Newark Liberty (EWR). These nonstop flights typically take between 2.5 and 3 hours, with round-trip airline tickets generally ranging from $150 to $350 depending on seasonal demand and how far in advance you book.

Once you land in the New York area, Montauk is located approx. 120 miles further east on the tip of Long Island.

Travelers can complete this final leg by renting a car and driving 2.5 to 3 hours, taking the Long Island Rail Road (LIRR) from Penn Station for a scenic 3- to 3.5-hour train ride, or booking a seat on the Hampton Jitney bus service, which takes roughly 3.5 to 4 hours. While flying and transferring is the overall fastest method to reach the East End from Chicago, it does require managing a multi-modal journey from the airport to the coast.

🚗 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 From Chicago to Montauk

Travelers can choose between two main long-distance routes to New York City before completing the final leg to the Hamptons.

For train enthusiasts, Amtrak operates a scenic route from Chicago to New York Penn Station that takes between 19 and 21 hours.

Alternatively, bus lines like Greyhound and Megabus offer long-distance routes from Chicago to NYC in roughly 15 to 17 hours. Once you arrive in Manhattan, you will need to connect to the final East End leg: either take the Long Island Rail Road (LIRR) for a direct 3- to 3.5-hour train ride straight to Montauk, or book a ride on the Hampton Jitney bus service, which typically takes 3.5 to 4 hours.

In terms of pricing, these multi-step public transit options are quite economical. Long-distance tickets from Chicago to New York generally range from $100 to $200, while the local NYC-to-Montauk segment costs an additional $30 to $60. While this combined train and bus method delivers a budget-friendly and visually stunning journey across the country, the primary drawback is the exceptionally long overall travel time.

🚖 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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Travel Cost Summary

Travel Mode	Duration	Cost (per person)	Notes
Flight (Chicago → NYC + drive/train)	6–7 hours total	$180–$400	Fastest overall; requires transfer to Montauk
Driving (Chicago → Montauk)	14–15 hours	$130–$180 + tolls	Scenic but long; flexible for road trip stops
Train (Chicago → NYC → Montauk)	22–25 hours	$150–$250	Very long but scenic; multiple connections
Bus (Chicago → NYC → Montauk)	19–21 hours	$130–$220	Budget-friendly; slowest with transfers
Local Transport in Montauk	N/A	$10–$90/day	Cars best for exploring beyond downtown

FAQs About How to Get to Montauk From Chicago

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