What Should I Know Before Moving From Long Island to Chicago, Illinois?

Moving from Long Island to Chicago means trading suburban sprawl and coastal living for a dense, urban city built around neighborhoods, architecture, and a true four-season lifestyle. Chicago offers strong career opportunities, cultural depth, and relative affordability compared to New York—but winters, property taxes, and city-style living require a mindset shift for many Long Islanders.

Cost of Living & Lifestyle Comparison

Chicago is more affordable than Long Island in many respects, though costs vary significantly by neighborhood.

Here’s how the shift typically looks:

  • Home prices are lower than most Nassau County neighborhoods, especially outside prime areas

  • Property taxes can be high, particularly in certain suburbs

  • Illinois has a state income tax, but at a flat rate

  • Utilities are moderate, with higher heating costs in winter

  • Dining, entertainment, and parking are generally more affordable

Lifestyle differences are noticeable:

  • True city living with walkable neighborhoods

  • Shorter commutes for many professionals

  • Strong neighborhood identity over town boundaries

  • A vibrant cultural and food scene

  • Cold winters balanced by active summers

For many movers, Chicago offers big-city energy at a lower cost than New York.

Employment & Opportunities

Chicago has one of the most diversified economies in the country, appealing to professionals across industries.

Key industries include:

  • Finance and trading

  • Technology and startups

  • Healthcare and life sciences

  • Consulting and professional services

  • Manufacturing and logistics

Major employers and anchors include McDonald's, United Airlines, Boeing, Northwestern Medicine, and University of Chicago.

Chicago is also attractive to remote workers who want city amenities without coastal pricing.

Education & Schools

School quality varies widely by neighborhood and suburb, making location choice critical for families relocating from Long Island.

Well-regarded options include:

  • Select Chicago Public School magnets

  • New Trier Township High School District

  • Evanston Township High School

  • Hinsdale Central High School

Private schools are common and often part of relocation decisions.

Higher education institutions anchor many neighborhoods and drive local economies.

Real Estate Practices: What’s Different?

Illinois real estate practices differ from New York in a few important ways.

Key differences include:

  • Attorneys are typically involved, but the process is faster

  • Property taxes play a larger role in long-term cost planning

  • Condos and multi-unit buildings are common

  • HOA associations are frequent in urban areas

  • More inventory compared to coastal markets

Homes often emphasize location, walkability, and architectural character over lot size.

Eric Berman REALTOR® can connect you with trusted Chicago-area agents who understand relocation needs and neighborhood dynamics.

Logistics of the Move

Relocating from Long Island to Chicago is a major move, but daily life often feels simpler once settled.

Be prepared for:

  • A less car-dependent lifestyle in the city

  • Extensive public transportation options

  • O’Hare and Midway airports with nonstop NYC flights

  • Cold winters and hot summers

  • Predictable commute patterns

Winter weather is the biggest adjustment for many New Yorkers.

Community & Quality of Life

Chicago is a city of neighborhoods, each with a distinct identity.

Popular areas include:

  • Lincoln Park: Family-friendly, green space, and walkability

  • Lakeview: Active, dense, and close to the lake

  • Evanston: Suburban feel with strong schools

  • Naperville: Family-oriented suburb with amenities

  • West Loop: Modern, urban, and dining-focused

Lifestyle highlights include:

  • Lakefront access and outdoor space

  • World-class dining and cultural institutions

  • Strong neighborhood pride

  • Professional sports and entertainment

  • A balance of affordability and urban energy

Chicago appeals to those who want culture, opportunity, and city living without coastal pricing.

Tips for a Smooth Transition

  • Understand property tax differences by area

  • Visit during winter to experience the climate

  • Explore neighborhoods carefully—vibe varies block by block

  • Consider public transit access when choosing location

  • Work with Eric Berman REALTOR® to connect with vetted local professionals

Your Move to Chicago

Relocating from Long Island to Chicago offers a shift toward density, culture, and affordability. While winters and taxes require planning, many Long Islanders find Chicago’s livability and depth a compelling alternative to coastal markets.

With Eric Berman REALTOR® guiding your relocation, you gain trusted insight, strong connections, and a clear plan to move with confidence.

FAQs

Is Chicago more affordable than Long Island?
Yes. Housing and daily expenses are generally lower, though property taxes can be higher in some areas. For a personalized comparison, visit 👉 https://www.theericbermanteam.com/contact-us

Which Chicago neighborhoods are best for families moving from New York?
Lincoln Park, Evanston, Naperville, and Hinsdale are popular for schools and community. Learn more at 👉 https://www.theericbermanteam.com/contact-us

How does buying a home in Illinois differ from New York?
Attorneys are involved, but closings are often faster and less complex. Get guidance at 👉 https://www.theericbermanteam.com/contact-us

What is the biggest adjustment for Long Islanders moving to Chicago?
Winter weather and urban density are the biggest changes. For relocation prep, reach out via 👉 https://www.theericbermanteam.com/contact-us

Is Chicago a good long-term place to buy a home?
Yes. Diverse employment and relative affordability support long-term demand. For market insight, contact 👉 https://www.theericbermanteam.com/contact-us

Eric Berman, REALTOR®
Compass Greater NY
917-225-8596
eric@ericbermanre.com
www.theericbermanteam.com