Tips for Moving to Chicago: Your Complete Guide to Life in the Windy City

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Whether you're relocating for a new job, returning to the Midwest, or simply seeking a vibrant urban lifestyle, moving to Chicago is an exciting step. Chicago is a city full of iconic architecture, known as a delicious food city, and has world-class museums, lakefront scenery, and a deep cultural identity. 

As with any major move, arriving prepared makes the transition smoother, especially if you're navigating neighborhoods, weather patterns, transportation, and the everyday realities of settling into a new home.

For many new residents, River North — home to The Gallery on Wells — becomes the ideal landing spot. It’s walkable, centrally located, filled with dining and cultural options, and well positioned for both personal and professional life. Whether you're moving to River North specifically, or starting your Chicago life in a different neighborhood, this guide will help you prepare for the move and understand what to expect once you arrive.

This comprehensive relocation guide covers everything from what to know before moving to Chicago, to how to select a neighborhood, to understanding the weather, transit, cost of living, logistics, cultural highlights, and how to settle in quickly. Think of this as your step-by-step pathway to feeling at home in the Windy City.

What to Know Before Moving to Chicago

Before packing boxes or booking movers, it helps to understand the basics of living in Chicago. Relocating here may feel different depending on where you're moving from, but there are a few realities that apply to nearly everyone.

Chicago Is a City of Neighborhoods

When people picture Chicago, they often think of the skyline, but residents think in terms of neighborhoods. These communities each offer their own character, architecture, restaurants, green spaces, culture, and lifestyle. That means that choosing a neighborhood is often as important as choosing an apartment.

For example, River North is known for its galleries, restaurants, walkability, and central location, making it a popular choice for professionals and creatives. Other well-known neighborhoods include:

  • West Loop: Trendy, full of restaurants, residential lofts, and many corporate headquarters.
  • Lincoln Park: Tree-lined streets, parks, family-friendly atmosphere, lakefront paths.
  • Lakeview: Lively, diverse nightlife, Wrigleyville (read: baseball culture), easy transit.
  • South Loop: Museums, historic buildings, proximity to the lakefront and downtown.
  • Logan Square: Artistic, independent shops, local bars and cafés.

 

Before moving to Chicago, spend some time researching neighborhoods, or if possible, visiting them in person.

Chicago’s Seasons Are Part of Its Identity

If you’re moving to Chicago from a warm climate, prepare for true Midwestern weather. One that features four distinct seasons, each with its own personality. 

While winters can be cold and snowy, with temperatures dipping below freezing, summers are hot, humid, and sunny, but as it is, those features mean it’s perfect for lakefront activities. 

Keep in mind that Springs are beautiful but often unpredictable, and though Fall is similarly back and forth with how you’ll need to dress, it also is crisp, colorful, and considered many residents’ favorite season.

Your wardrobe, commute habits, and even apartment prep will change from season to season, so it helps to know what to expect.

Chicago’s Transit System Makes Urban Living Easy

The city’s public transit network includes:

  • CTA trains (“the L”): connecting much of the city and O’Hare Airport
  • CTA buses: extensive routes throughout neighborhoods
  • Metra commuter rail: ideal for suburban commuters
  • Divvy bike share: for short trips in warmer months
  • Walkability: especially in downtown neighborhoods like River North

Many residents choose to live without a car, especially if they’re in central neighborhoods. If you do bring a vehicle, ensure you understand parking rules and requirements ahead of time.

Choosing the Right Neighborhood When Moving to Chicago

From your commute to your social life to your favorite coffee shop, finding the right neighborhood can shape your daily life

Below is a detailed look at how to evaluate Chicago neighborhoods when you’re relocating.

Understand Your Priorities

Start by asking yourself:

  • Do I prefer a fast-paced or quiet environment?
  • Do I want to be near the lakefront?
  • Do I need close access to transit?
  • Am I seeking nightlife, dining, or cultural amenities?
  • How important is proximity to work?

 

Each neighborhood offers different strengths, so knowing what matters most helps narrow the options.

Why Many New Residents Choose River North

Due to the facets of the lifestyle, River North, home to The Gallery on Wells, is one of Chicago’s most desirable neighborhoods for people relocating from other cities. It offers:

Walkability & Convenience

Everything you need, such as grocery stores, gyms, pharmacies, coffee shops, and restaurants, is just steps away.

Dining & Entertainment

River North is home to some of Chicago’s most iconic restaurants, rooftop lounges, and cocktail bars.

Proximity to the Loop

If you’re working in an office downtown, your commute is easy, and especially during warmer months, often walkable.

Artistic Identity

River North’s gallery district brings creativity into the urban landscape that delights not just tourists but residents, too.

Transit Access

Two major CTA lines, multiple bus routes, and easy expressway access are all at your fingertips in River North.

For people moving to Chicago without knowing exactly where they want to land, River North is a natural and practical starting point.

A Look at Other Popular Neighborhoods for Newcomers

West Loop

Perfect for food lovers, young professionals, and those who enjoy modern apartments, rooftop pools, and proximity to corporate offices like Google and McDonald’s.

South Loop

Walkable, close to lakefront parks, museums, and an increasing number of new residential developments.

Lincoln Park

More residential, with beautiful historic homes, boutique shopping, and access to the greenspace (and the zoo) at Lincoln Park.

Wicker Park, Bucktown, & Logan Square

Trendy, artistic, you’ll find local coffee shops and independent boutiques in the areas surrounding the CTA Blue Line.

Lakeview

Youthful, energetic, perfect for renters seeking a vibrant nightlife scene, ample public transit, and a nearby home to Wrigley Field.

Exploring these neighborhoods (in person or virtually) is a foundational step for anyone moving to Chicago.

What to Expect When Moving to Chicago

Cost of Living

Chicago is more affordable than New York, San Francisco, Boston, or Washington, D.C., but more expensive than many Midwestern cities.

Your cost of living will depend on:

  • Neighborhood
  • Housing type
  • Parking needs
  • Transit decisions
  • Lifestyle preferences

 

River North and West Loop tend to be on the higher end, while neighborhoods located farther from downtown usually offer more budget-friendly options.

Weather Preparation

Unless you’re from a nearby (possibly even more northern state like Wisconsin, Minnesota, or Michigan) you will hear this multiple times: preparation for winter is essential. Items you’ll want include:

  • A heavy winter coat
  • Waterproof boots
  • Layering sweaters
  • Gloves, scarves, and hats
  • An umbrella for fall and spring
  • A compact snow brush for your car (if you have a car)

 

Inside your apartment, many residents also invest in:

  • Humidifiers
  • Weatherproofing for drafty windows
  • Cozy bedding and soft lighting

 

Summer requires far less gear, but you’ll want:

  • Lightweight clothing
  • Sunscreen
  • Comfortable walking shoes
  • A reusable water bottle for long walks or bike rides

 

Transportation & Commuting

Chicago is highly connected by transit. Your commuting options include walking (common in River North, the Loop, and West Loop), CTA trains and buses (most efficient option for daily travel), biking (which is easy with dedicated bike lanes), driving and ride shares.

Chicago also has two airports with O’Hare (ORD) being the larger one found on the northwest side of the city and is the home of United Airlines, in addition to being a choice airport for global travel connections. Midway (MDW) is found on the Orange Line (ORD is on the Blue Line) and is used primarily for domestic flights, some international flights (mainly for flights to and from Mexico), and is a Southwest Airlines hub.

Safety & City Awareness

As in any major city, awareness matters.

Follow basic precautions like:

  • Stay aware of your environment
  • Avoid late-night travel through unfamiliar areas
  • Keep valuables stored in zipped bags
  • Pay attention to transit times and routes
  • Use well-lit streets and main pedestrian pathways

Chicago is welcoming and full of vibrant communities, but smart city habits help ensure comfort and confidence.

Logistics of Moving to Chicago

Decide Whether to Bring a Car

Many people moving to Chicago debate whether to bring a car. Consider the pros and cons of both, and use our lists below to facilitate factoring in whether you should bring a car or leave a car.

Bring a Car If:

  • You travel outside Chicago regularly
  • You work in a suburb
  • You need weekend accessibility to drives outside the city

Leave the Car If:

  • You live in a walkable neighborhood like River North
  • You work downtown
  • You want to avoid the cost of parking
  • You prefer transit or walking

Parking in Chicago can be expensive, and winter makes street parking less convenient. Many urban residents choose to go car-free.

Hire a Moving Company Familiar with Chicago

Urban moves are different from suburban ones. Look for movers who understand:

  • Loading dock coordination
  • High-rise move-in protocols
  • Service elevator scheduling
  • Parking permit zones
  • Downtown traffic timing

If you're moving into The Gallery on Wells, the Management Office can help explain:

  • Approved elevator usage
  • Move-in hours and restrictions
  • Loading dock location
  • Required insurance documents from your moving company

Getting these details right will save time and prevent delays.

Understand Utility Setup

When moving to any Chicago apartment, plan for:

  • Electricity (ComEd)
  • Internet installation
  • Optional cable or streaming services
  • Renter’s insurance
  • Updated mailing address

If you're relocating to The Gallery on Wells specifically, your ComEd account and renter’s insurance must be active before key pickup.

How to Settle Into Chicago Quickly

Get to Know Your Local Spots

Chicagoans love their neighborhood favorites — the café where they get their morning latte, the grocery store on their block, the restaurant where they take friends, the gym they frequent.

Within your first few weeks, map out the following, with some tips for those moving into The Gallery:

  • Your nearest grocery store

There are some smaller grocery stores or markets, but your closest grocery store will be the Whole Foods Market on Chicago and State or the newly-opened Aldi on Dearborn and Superior.

  • A local coffee shop

Just next door is Around the World Coffee, while two blocks north is an OUD and a Goddess and The Baker… you’ll have your cup of coffee in hand in no time.

  • Pharmacy

Like any big city, you’ll be able to find a pharmacy on most neighborhood corners, with the closest being a CVS, a block north of The Gallery.

  • Dry cleaner

Although not nearly as populated around this part of the city, there are a handful of dry cleaners in the River North, with a few found between two and six blocks away in all directions.

  • Transit stop

Luckily there are many locations nearby that you can find a bus stop shelter or pop over to an L stop. The Chicago Brown/Purple Line stop is the nearest for L options, but there is a bus stop just on the corner outside of The Gallery’s front doors. Additionally, there are bus stops found two blocks away on Orleans as well as a block east on LaSalle. 

  • Favorite local takeout spot

Regardless of your preferences for cuisine type, there are countless options for takeaway food on a snowy Friday or an it’s-too-hot-to-cook summer evening. From wings and pasta to Greek, French, and Middle Eastern cuisine, you’ll have any type of food nearby that you’re seeking.

In River North, this might include Foxtrot, Whole Foods, Café Crèmerie, Jewel-Osco, Ema, or any of the dozens of local favorites within walking distance.

Enjoy the Lakefront

Few cities offer lake access the way Chicago does. Once you’ve moved, explore:

  • Lakefront Trail
  • Ohio Street Beach
  • Oak Street Beach
  • Lakeshore Drive running paths
  • Riverwalk restaurants and views

Whether you walk, bike, run, or simply sit by the water, the lakefront becomes a favorite relaxation spot for most residents.

Try Chicago’s Cultural Staples

Nothing helps you feel at home like participating in the city’s traditions:

  • Deep dish pizza (Giordano’s, Lou Malnati’s, Pequod’s)
  • Tavern style pizza (Michael’s in Uptown or Dante’s in Ukrainian Village)
  • Chicago-style hot dogs
  • Neighborhood street festivals
  • Outdoor concerts at Millennium Park
  • Museum visits (Art Institute, Field Museum, Museum of Contemporary Art)
  • Architectural river cruise
  • Sports events (Cubs, Sox, Bulls, Blackhawks, Bears, Stars, Fire, Sky)

Your first year in Chicago is the perfect time to explore.

Build Community

Moving to a new city can feel overwhelming without community. Try:

  • Joining a gym or fitness studio
  • Taking a class or hobby workshop
  • Joining a young professional group
  • Participating in neighborhood events
  • Getting to know neighbors in your building

Residents at The Gallery on Wells often meet through amenity spaces, social events, or shared routines like morning gym visits or rooftop gatherings.

Why Many People Moving to Chicago Choose River North

With so many neighborhoods to choose from, River North stands out for newcomers because it strikes the ideal balance between lifestyle, convenience, and culture.

Here’s why, from the location to the culture:

Central Location

River North places you minutes from:

  • Downtown offices
  • Lakefront recreation
  • Chicago’s cultural core
  • Restaurants and entertainment
  • Public transit hubs

Whether you walk, bike, or take the train, the city feels accessible from this neighborhood.

Vibrant Dining & Nightlife

From Michelin-starred restaurants to hidden cocktail lounges or speakeasies, River North is one of the city’s most dynamic dining districts.

Art & Design Culture

Home to galleries, architecture firms, and curated retail, River North offers a creative atmosphere that appeals to newcomers.

Modern Residential Living

Many people relocating to Chicago want a building with:

  • Luxury amenities
  • Modern layouts
  • Fitness and wellness spaces
  • Social lounges
  • Rooftop views

The Gallery on Wells offers all of these features, making it a popular choice among new arrivals.

Moving to Chicago with Confidence

Relocating to a new city is a major life milestone, and moving to Chicago offers endless opportunities to build a lifestyle filled with culture, community, and comfort. Whether you’re drawn to the lakefront, the restaurant scene, the architecture, or the energy of urban living, Chicago welcomes newcomers with open arms.

The key is preparation — understanding neighborhoods, planning your move, learning how transit works, and settling into routines that make you feel at home. River North and The Gallery on Wells provide an ideal starting point for your life in Chicago, giving you walkability, access, and a supportive residential environment designed for modern urban living.

Once you’ve moved, take time to explore, connect, and enjoy. Chicago rewards curiosity — and soon enough, you’ll feel like you’ve lived here for years.

Welcome to your next chapter in the Windy City.