=The Ultimate Chicago Guide: Explore the Windy City Like a Local
Discover Chicago, IL with Power Haus Women | Curated by Anna Swiech
Why Chicago?
Whether you're planning a weekend getaway, moving to the city, or just looking for your next spot to vibe in—welcome to your go-to guide to all things Chicago. I’m Anna Swiech, your local expert, food-obsessed city girl, and the person who will 100% convince you to fall in love with this place.
Chicago isn’t just the land of deep-dish and skyscrapers (though, yes—we love both). It’s a city full of personality, flavor, and moments you didn’t know you needed. And I’ve put together a little something to help you experience it like a real local—not just someone following the Google Maps stars.
Let’s go ✨
Meet Me: Anna, Your Chicago Insider
I grew up in the suburbs of Chicago, and honestly? Younger me would be screaming knowing that I now get to help people find their dream homes all over this incredible city. From lakefront sunrises to cozy winter nights in a brick walk-up, there’s something magical about every pocket of this place—and I’m all in.
Quick things to know about me:
🏃♀️ Hot yoga & pilates enthusiast
🍣 Sushi? Always.
📚 Reading with a martini in hand = yes please
🎉 Life of the party and your go-to market expert
Why Chicago is That Girl
Chicago is historic, iconic, and somehow always reinventing itself. It’s where the first skyscraper was built, where jazz legends were made, and where architecture still takes your breath away.
The neighborhoods here have soul—like actual, lived-in, culture-rich energy. From Chinatown to Little Italy to Pilsen’s vibrant street art, every area brings its own flavor.
It’s Known For:
🎭 Culture: The Art Institute, Broadway in Chicago, and live music everywhere
🏙 Architecture: Hello, Willis Tower and those skyline views
🎶 Music: Blues, jazz, and everything in between
📚 Top-tier Schools: University of Chicago, Northwestern, DePaul
Neighborhoods To Explore
Chicago is a city of neighborhoods, each with its own vibe:
West Loop – Foodie central and industrial-chic aesthetics.
Lakeview – Family-friendly with lakefront charm.
Lincoln Park – Green spaces meet upscale living.
River North & Old Town – Culture, comedy, and nightlife.
Uptown & West Town – Diverse, artsy, and up-and-coming.
Pilsen & North Center – History-rich and full of local gems.
Anna’s Chicago Bucket List
Don’t leave without checking off these must-do’s:
Sushi Omakase at Sushi
Get festive with a Christmas Shot at Butch McGuire’s
Sweat it out at Studio Three (code: AXMVIP for a free class!)
Customize a hat at Alice & Wonder
Explore happy hour hotspots across the city
Take in the views from 360 Chicago (John Hancock Building)
Snap a selfie at The Bean in Millennium Park
Do a restaurant crawl in West Loop
Window shop on Michigan Ave. and State Street
Catch a Broadway in Chicago performance
Local Favorites (POIs You’ll Want to Know)
☕ Coffee Shops That Actually Hit:
Sawada Coffee (aesthetic goals)
Dialtone (WFH + espresso dream)
Botanical Cafe (greenery + vibes)
🍽 Restaurants I’m Always Craving:
Pequod’s Pizza (deep dish royalty)
Monteverde (pasta dreams come true)
Bronzeville Winery (black-owned & beautiful)
🌳 Outdoorsy Moments:
Lincoln Park Zoo (yes, it’s free!)
Lakefront Trail (biking with views)
Montrose Beach (bring a picnic)
🛍 Shop Til You Feel Something:
Armitage Ave – boutique central
Southport Corridor – cozy and walkable
Michigan Ave – your designer fix
🚇 Getting Around:
“L” train = easy peasy
Union Station + O’Hare for travel days
Biking? Totally doable.
Anna’s Tried-and-True Spots
Want to live like a local? Start here.
🍸 City Sips:
Lyra – get the Hades cocktail
The Aviary – wild mixology you need to try once
Berkshire Room – Dealer’s Choice is always a good time
🍰 Dessert Heaven:
Mastro’s – Butter Cake. That’s it.
Stan’s Donuts – Lemon Pistachio is the move
Lyra – Bougatsa, trust me
💻 WFH Cafés:
Aster Hall – upscale food court vibes
Fairgrounds – chill but productive
Lululemon Café – yes, it’s a thing and yes, it slaps
💅 Wellness Musts:
Lume Wellness – chic and calming
The Now Massage – dreamy
@Ali_wilsaveyourhair – she’s magic
More Than a Visit—A Community
AT PHW, our goal is more than just highlighting Columbia’s hotspots. We aim to connect you to the heart of the destination and its vibrant communities! Whether you're planning to make Columbia your home or just exploring, we're here to guide you every step of the way. Ready to dive into the history and culture of Columbia, SC? Get your copy by commenting “GUIDE” below or REQUEST A COPY HERE!
About Power Haus Women & Our Exclusive Destination Guides
At Power Haus Women, we’re a national network of female real estate advisors committed to making your city exploration or relocation both seamless and enjoyable. Our detailed destination guides are designed to be your personal resource for discovering everything a city has to offer, curated by our Market Partner’s who work and play in these destinations!
From local history and architecture to top neighborhoods, bucket list items, shopping, fitness, and dining, our guides help you make the most of your new locale.
Get In Touch With Anna
Whether you're just dipping your toe into the Chicago experience or seriously considering a move, I’ve got you. This city is full of opportunities, energy, and really good food. Let’s make it yours.
📩 Email me: anna.swiech@compass.com
📱 Follow me on Insta: @annaxmargaret
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