"Either you love Chicago, or you are wrong"

And that I do. I have spent the last 12 years here. I didn’t necessarily intend to stay this long; it just sort of happened. Easy to see why though – this is a great city. It’s cosmopolitan yet approachable. Large but manageable. Fun but (mostly) affordable. The food and drink, the entertainment, the events, the lake…there’s no shortage of things to see or do. Some days it feels like I’ve barely scratched the surface, but as I’ve spent a good deal of my formative years dining and bopping around here, I felt it justified a post.

This is my version of a “best list,” and what I would wish for a visitor to have in hand as the plane glides over Lake Michigan, descending into our fair city. While Wrigley Field is iconic, deep-dish pizza is delicious, and it wouldn’t be a trip here without a picture at the Bean, so much of what I love about Chicago is not in the guidebooks but in its neighborhoods. I've tried to cover as many of them as possible in the below.

Sadly, though, the time has come to spread my wings and say goodbye to the Windy City. I’ve never lived outside of Illinois – not as a child, not for college, not for a job! Also, you may have heard, it’s pretty cold here.

I am the biggest fan of sunshine and warm weather; it’s a small miracle I’ve lasted this long.

Without further ado, let me pay homage to some amazing places and spaces I’ve discovered over the years. May you find a new gem if you call Chicago home, and may you find some inspiration if you stumble upon this and plan on visiting!

Best Bar

I cannot possibly whittle this down to just one. Consider it a bonus round! They are – Scofflaw (Logan Square), Sparrow (The Gold Coast), The Charleston (Bucktown), and Marty's Martini Bar (Andersonville).

Best Beach

12th Street Beach (Near South Side), just around the corner from the Planetarium, is most idyllic to me. Though Montrose Beach (Uptown) has The Dock, which is about as close to eating on the water as you can get. Take your pick!

Best Bookshop

Ravenswood Used Books (Ravenswood) – plan to spend a good hour in here. It’s messy but charming AF (exactly as you’d expect a used bookstore to look, with delightful nooks and crannies everywhere).

Best Boutique (clothes)

Winnie Cooper (Roscoe Village) – only discovered this shop recently. But I recall wanting to buy just about everything. The owner is a Chicagoan who left corporate America to start the biz.

Best Boutique (gifts)

RR #1 (Noble Square) – this place is the definition of a hidden gem. An unassuming storefront on Ashland Avenue but filled to the brim (not kidding about this!) with treasures.

Best Breakfast/Brunch

Tweet Let's Eat (Uptown) – eclectic decor, fun atmosphere, and a whole lotta breakfast burritos to choose from, what's not to love? Plus, they give you cake as an appetizer.

Best Brewery

Metropolitan (Avondale) – good beers, dogs welcome, stunning sunsets – ‘nuff said.

Best Burger

This is a TOUGH category, but I'm going to go with Mott Street. It's a double patty with sweet potato frizzles, hoisin aioli, pickled jalapenos, miso butter, and American cheese. I like getting it at Time Out Market (Fulton Market).

Best BYOB

Irazu (Wicker Park) – it's a tiny place but not lacking in flavor or ambiance! Costa Rican, for those unfamiliar.

Best Cocktails

The Berkshire Room (River North) – they have a 'Dealer's Choice' option where you pick your spirit, glass, and profile. Each time I've been the result has been no less than perfection, and the bartenders are really fun too. Finally, it oozes old world Chicago.

Best Coffee

Hexe (Avondale) – nothing would make me happier than sitting on this patio, coffee and skull cake (ask about it!) in hand, with a couple pals.

Best Date Spot

Big Mini Putt Club (Wicker Park) – I tend to like an activity date over "let's grab a drink," though admittedly, sometimes a drink is nice to take off the edge. This is the perfect combination of both, and at just nine holes, it doesn't keep you out too long. Though if having a good time, there are plenty of watering holes within walking distance to continue the conversation!

Best Doughnuts

Beacon (Lincoln Park) – these are vegan but TRUST ME you wouldn’t know it. Plus, the shop is in an alley. How neat is that?

Best Happenings

In the spring...The best Chicago street festival, Maifest (basically a scaled-down Oktoberfest), in Lincoln Square.

In the summer...Farmer's market (Wicker Park & Green City Market are two classics).

In the fall...Leaf peeping. May I suggest the University of Chicago campus in Hyde Park? It's particularly beautiful in the fall + just an iconic institution in the city.

In the winter...A holiday show or double feature at The Music Box in Lakeview.

Best Ice Cream

Cone (West Town) – get the 'Netflix & Chill.' I've never tasted anything quite like it before (in the best way).

Best Live Music

Rosa’s (Logan Square) – a lesser-known blues joint opened by an Italian immigrant and his mother. Needless to say, it feels like coming home here! Amazing music any night you go, and only ~$20/show.

Best Outdoor Space

The 606 (West Side) – 5.4 miles of bliss. I've spent many a run/walk/bike here, and it feels like each time, I discover something new. Plenty of points to stop and take in the people-watching, read a book, or pop off and on for food or drink.

Best Beer Garden

The Northman (Streeterville) – I was sad when its predecessor, a cozy pub in Lincoln Square, closed – but this is quite the consolation prize. Set along the river, this spot was made for a Saturday or Sunday afternoon.

Best Park

Mary Bartelme (West Loop) – the only hills you will find in Chicago (ha). Moreover, this park just feels like LIFE.

Best Patio

Pilsen Yards (Pilsen) – you know when a place just has a VIBE? This is one of those.

Best Pizza

Fat Chris’ (Andersonville) – I may be critiqued for this because it’s neither deep dish nor tavern-style, but it is so. damn. good.

Best Random Adventure

The Plant (Back of the Yards) – I discovered this as part of Chicago Architecture Foundation's Open House one year. It's a repurposed industrial meatpacking facility that now serves as a living laboratory demonstrating techniques for reimagining waste as a resource, achieving economies of scale, and incubating small businesses. Super cool.

Best Rooftop

Gene's Sausage (Lincoln Square) – I couldn't leave encased meat off the list in some way, shape, or form. But that's not why it's my favorite! It's just so unexpected. A high-end grocer with a rooftop? And to be found not downtown, but on the north side? Not to mention, a big ol' cow sculpture anchors it, which is fabulous. Just be sure to call before you make the trek, because their hours can be funky.

Best Sandwich

Humboldt Haus (Humboldt Park) – just north of the park. Bonus, it's a slashie (another uniquely Chicago thing). I personally like the 'West Sider.'

(a VERY close runner-up is the Cuban Breakfast Sandwich by Cubano Bros inside the French Market!)

Best Theater (plays/musicals)

Chicago Shakespeare Theater at Navy Pier (Streeterville) – a lot more than just Shakespeare! I've seen multiple productions here and across the whole I just think they're really well-done and innovative shows.

Best Theater (improv)

Logan Square Improv (Logan Square) – Chicago might very well be the home of improv, and you can't go wrong with some of the bigger venues, but personally I like a hole-in-the-wall theater and this one should have you laughing most of the night.

Have you been to any of these? What have I missed?! Let me know in the comments.

Austin, here I come!