Chicago Travel Guide

Discovering the Beautiful Windy City

Chicago has always been my home. It's the Windy City, the Second City, the White City, My City. The city I was born to and the city my family has called home for four generations now.

And while many might be keen to write off Chicago as a sub-par NYC or a more Midwestern San Francisco, underestimating the Windy City's beauty, liveliness, and positive attitude despite all odds would be a huge mistake.

Chicago is a vibrant, evolving urban paradise full of some of the most delicious food and most breath-taking experiences you can find anywhere in the world. It's a quirky place, a weird juxtaposition of so many extremes. Home to Oprah, Kanye West, and Harrison Ford alike. And yes, we really do dye our river green every year!

So isn't it about time I shared my guide to our gorgeous city with you? 

What To Do & See

In our city, you can find just about any experience and any niche. It's full of all sorts of surprising and magical spaces to visit, absorb, and learn from. And there's truly something for everyone to enjoy!

This is just a short list of a few of my absolute favorites that I always recommend to first-time visitors. Feel free to click on any of the names to learn more!

Where To Eat

Chicago has one of the most innovative and flourishing food scenes in the States and there are countless options to choose from, both good and bad. These are a few of my absolute favorites and ones that almost never fail to disappoint me when I want a good, Chicago-centric meal!

Nico Osteria Chicago Brunch

The Allis Breakfast Soho House Chicago

Dox Chicago Greek Restaurant Wicker Park

Peninsula Hotel Chicago Holiday Afternoon Tea

Peninsula Chicago Pierrot Gourmet Raspberry Macaron Sandwich

Expat on Green Chicago Summer Restaurant

Sprinkles Cupcake ATM Chicago

Duck Duck Goat Chicago Chinese Restaurant

Gemini Chicago Restaurant

Chic Chicago Summer Outfit Black and Gold Chloe Zara

Green Burgundy Fall Outfit

Denim Cork Red Lip Summer Outfit

LOGISTICS

Chicago often intimidates visitors -- it's a big enough city where you can't walk to EVERYTHING so some planning is involved. It doesn't help that we have dozens upon dozens of hotel options to choose from too. And our weather (especially our notorious Chiberia winters) can really scare people. Here are just a few quick tips and tricks to keep in mind when planning a visit to the Windy City!

HOW TO GET AROUND

Whenever I can I always prefer to walk in Chicago. However there is ample access to public transit (via city buses or the 'El' trains) as well as plenty of cabs and Ubers to make getting around really easy. And significantly cheaper than many other large, urban cities!

WEATHER

Weather in Chicago can be notoriously tricky. Summer is certainly Chicago's best tourist season but spring and fall often have wonderful weather with less crowds. Regardless of when you visit, bring plenty of layers and something to survive any rain or snow that may come during your visit. 

Nico Osteria Chicago Lunch Gold Coast

Peninsula Chicago Hotel Girl's Staycation

Purple Pig Chicago Restaurant

Neighborhoods

Chicago is often called a city of neighborhoods. Depending on which you choose you can find just about any vibe and atmosphere you desire and each neighborhood is more distinctive than the next.

My absolute favorite Chicago neighborhoods are all listed below!

OLD TOWN

LINCOLN PARK

LAKEVIEW

WEST TOWN

THE "LOOP"

RIVER NORTH

WICKER PARK

LOGAN SQUARE

HYDE PARK

My Curated Lists

Loving Chicago like I do, I tend to share and write about it a lot here on the blog. Here are a few of my most useful Chicago posts on more specific topics.

How to Experience Chicago Like A Local

Ignore the Tourist Traps and Get Chicago Deep Dish Pizza at Pequod's

Wait Longer Than You Want to For a Table at Au Cheval

Spend a Day Working from Couches in The Allis

See the Cloud Gate at Dawn

Walk Along the Lakefront (Especially Barefoot on the Beach)

Spend an Afternoon Drinking Wine Along the Chicago River

Take at least One Architectural Tour (Yes, Locals Take Them Too!)

Wander Through the Lincoln Park Zoo at Sunset

See a Cubs Game at Wrigley Field

By-Pass Drinks at Green Door Tavern & Head to the Hidden Speakeasy in the Basement


"She is novelty; for she is never the Chicago you saw when you passed through last time."

-- Mark Twain


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