What’s It Like to Live in Chicago? A Lifestyle Guide

Chicago is more than just its iconic skyline — it’s a vibrant amalgamation of neighborhoods, culture, and career opportunities that make each day unique. From lakeshore strolls and rooftop brunches to bustling streets filled with local boutiques, the city offers something for every lifestyle.

The best part? Our Luxury Living agents don’t just lease apartments here — they live in the city, explore its hidden gems, and know firsthand what it’s really like to live in Chicago. Let’s take a closer look.

Thinking about making the move? — Check out our Relocation Guide for an inside look at neighborhoods, lifestyle perks, and apartment options tailored to your needs.

Neighborhoods + Featured Properties

Chicago’s neighborhoods each offer a distinct lifestyle, and the city’s luxury apartments reflect that personality. Whether you’re drawn to lakefront living, vibrant nightlife, or tree-lined streets, there’s a perfect fit for you. And our curated properties give you a front-row seat to it all.

Streeterville — The Saint Grand

Steps from Navy Pier and the Magnificent Mile in the highly coveted Streeterville neighborhood, The Saint Grand combines lakefront views with modern interiors. Spacious layouts, floor-to-ceiling windows, and private balconies (in select units) let residents soak in sunrise and sunset over Lake Michigan. Amenities here are high-end and include luxuries such as a fitness center, outdoor pool, rooftop deck, and concierge services.

Available units range from convertible spaces to two-bedroom apartments, making it ideal for professionals seeking both convenience and elevated city living.

River North — The Leo

If nightlife, dining, and Loop adjacency are top priorities, The Leo delivers. Located in the lively and sophisticated River North neighborhood, this high-rise building offers panoramic skyline views, resort-style amenities, and work-from-home-friendly spaces that put the best of Chicago at your doorstep. Units currently available include one-bedroom layouts.

Fulton Market/West Loop — Maeve on Ashland and Monroe Laflin

For food lovers and culture seekers, these buildings place you in the heart of Chicago’s culinary capital: West Loop. Maeve on Ashland offers contemporary interiors, rooftop terraces, and designer finishes, while Monroe Laflin pairs boutique charm with spacious layouts and skyline-facing balconies (again, in select units). Both are steps from Fulton Market dining, Greektown, and entertainment at the United Center. 

Get in touch with our team today to inquire about available units.

Lincoln Park — No. 508 and Norweta

Perfect for families or those seeking green space, the Lincoln Park area blends tree-lined streets with boutique shopping and easy access to DePaul University. As far as buildings go, No. 508 features modern layouts and private balconies, while Norweta provides resort-style amenities and expansive floor plans.

Available units include three-bedroom penthouses at No. 508 and three-bedroom apartments at Norweta.

River West/Wicker Park — Seven 10 West and Wicker Park Connection

Eclectic, artsy, and full of character, River West and Wicker Park are two neighborhoods that attract those who value proximity to shopping, nightlife, and cultural vibrancy. 

Seven 10 West, one of River West’s premier buildings, offers contemporary apartments with skyline views, while Wicker Park Connection in Wicker Park delivers modern finishes with a neighborhood that buzzes with creativity. 

Units range from one-bedroom layouts at Seven 10 West, to one- and two-bedroom apartments at Wicker Park Connection.

Thinking about which neighborhood fits your lifestyle best? — Take our “Where to Live in Chicago Quiz” to discover neighborhoods that match your vibe, commute, and city priorities.

Lifestyle in Chicago: Day-to-Day Living

Living in Chicago means being immersed in a city that blends convenience, culture, and energy. Here’s what a typical day-to-day lifestyle offers:

• Walkable neighborhoods and transit: Living steps from shops, coffee spots, and offices, with CTA lines, Divvy bikes, and the Lakefront Trail makes getting around easy.
• Foodie haven: From deep-dish pizza to Michelin-starred dining, neighborhoods like West Loop, River North, and Lincoln Park deliver endless culinary options.
• Culture and entertainment: Live music, theater, museums, and seasonal festivals bring the city’s arts scene to your doorstep.
• Sports and fan energy: Iconic teams like the Cubs, Bulls, Blackhawks, and White Sox infuse the city with excitement and community spirit.
  

For young professionals planning their next move, our guide on Best Chicago Neighborhoods for Young Professionals is an essential resource to match lifestyle with location.

The Honest Pros and Cons of Living in Chicago

Pros:

Chicago is a city that effortlessly blends energy, culture, and convenience. Food lovers can indulge in everything from Michelin-starred restaurants to local deep-dish and global cuisine hidden throughout its neighborhoods. Sports fans and culture seekers have no shortage of options, with iconic teams, live music, theater, museums, and festivals keeping the city vibrant year-round.

Getting around is easy thanks to walkable streets and a robust public transit system, and luxury apartments here often offer better value than similar options in New York or Los Angeles. With a friendly, welcoming vibe and strong career opportunities spanning tech, finance, creative industries, and more, Chicago has a lot to offer newcomers and longtime residents alike.

Cons:

Full honesty: Chicago’s winters are famously long and cold, and adjusting to lake-effect snow can be a challenge for those moving from warmer climates. Parking and traffic in busy areas can also test your patience, and property taxes are typically higher than in many other states.

That said, most residents agree that the city’s culture, career opportunities, and unbeatable lifestyle more than make up for these drawbacks — which is why so many people choose to call Chicago home despite the chilly weather.

For a deeper look, check out our guide: Is Chicago a Good Place to Live? Top Things a Newcomer Needs to Know.

Career and Company Opportunities

Chicago is a thriving hub for professionals, home to Fortune 500 headquarters, major consulting firms, finance leaders, and top healthcare networks. Whether you’re seeking corporate growth, investment opportunities, or creative roles, the city offers a diverse career landscape. For more insight, see our guides to Top Companies in Chicago and Investment Firms in Chicago.

Cost of Living in Chicago

Compared with New York or Los Angeles, Chicago offers strong value for luxury living. From upscale apartments to curated dining and cultural experiences, the city balances high-end amenities with affordability. For a detailed comparison, check out our Comprehensive Guide to the Average Cost of Living in Chicago.

Moving from Other States to Chicago?

Planning a relocation? Explore our relocation resources to start planning your Chicago life:

• Moving from Los Angeles to Chicago
• Moving from Texas to Chicago
• Moving from Florida to Chicago
• Moving from NYC to Chicago
• Moving from Arizona to Chicago 

Find Your Ideal Chicago Apartment with Local Experts

Chicago offers neighborhoods and lifestyles to fit nearly every personality, whether you crave lakeside calm, bustling nightlife, or a foodie-focused daily routine. At Luxury Living, we make the transition seamless with our complimentary, concierge-level services. From personalized tours to curated apartment options and guidance through lease signing, our team knows the city inside and out and will help you find a home that matches your style, schedule, and priorities.

Ready to Start Your Search?

Whether it’s a high-rise with skyline views, a boutique loft, or a family-friendly Lincoln Park apartment, Luxury Living’s experts are here to guide you every step of the way. Connect with us today to discover your perfect Chicago apartment.