Photo by Sawyer Bengtson on Unsplash

I’m officially a city girl and have lived in Boston, San Francisco, and New York. You hear so much about each of these cities—all have their distinctive reputations—but for Chicago, there is exactly zero hype—and it’s completely underrated.

Since no one much talks about Chicago, I subconsciously had low expectations but was completely floored when I got there. It’s clean, cheap, has a great food scene, is easy to get around, has lots going on and an Americana charm. The weather was cold but the people were warm. Read on to see the little gems I found, and the ones I wish I had time for.

StayPineapple Hotel

Normally when I travel I stay in uniquely tiny, “affordable luxury” hotels. StayPineapple was a lovely stay and conveniently located across the street from the product marketing conference I was speaking at, but not Small Space, Big Taste-y enough to warrant it’s own blog post so I’m sharing here. The room itself was technically two rooms and bigger than my apartment (that happens quite a lot actually). It was immaculately clean and the bed was super comfy.

Little Goat Diner

Little Goat Diner is Stephanie Izard's (I guess she was a big deal on Top Chef) diner serving a huge menu of creative, gourmet takes on comfort food classics. I loved this fresh take on the classic diner with it’s international comfort food, bright buzzy vibes, and fast service.

I ordered “THIS LITTLE PIGGY WENT TO CHINA”—sesame cheddar biscuit, sunny side eggs, sichuan pork sausage, chili garlic chive sauce, gooseberries. It was DELISH.

Seems like diners are having a moment! Diners are, in general, warm, cozy, and casual—often open late or even 24 hours. The diner is a rather American tradition, and often serves American classic comfort foods, such as eggs & pancakes, grilled cheese sandwiches, burgers, fries, and local favorites.

Sawada Coffee

The first U.S. coffee shop of world renowned barista and latte art expert Hiroshi Sawada who first brought Seattle style coffee to Japan and now back to the U.S. in Chicago and New York. The industrial style café features a wall of windows facing Green Street and includes a custom painted espresso machine, wooden ping pong table, pinball machine, and punching bag. Guests can order from a curated menu of expertly crafted espresso and matcha-based drinks, including military lattes, cortados, cappuccinos, and boozy steamers, paired with a selection of camouflage Doughnut Vault doughnuts.

Fun vibe but it literally took 30 minutes for my cappucino to be made so next time I’ll just order my coffee black and get the time with my friend Mark back.

Chicago Classics

Every city has its food, and deep dish pizza and “dragged through the garden” hot dogs are Chicago’s. The hot dog is topped with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices, pickled sport peppers and a dash of celery salt.

Emporium Arcade

Emporium is a really fun arcade bar with pinball, skeeball, foosball (which I’m utterly horrible at), and pool tables. As a non-drinker, I appreciated that they had non-alcoholic beers and CBD drinks! It had a fantastically laid back vibe (maybe that’s just Chicagoans?!?) but I wish they had Pac-Man, Killer Queen, and a functioning dual-player shooting game.

River Walk & Architecture Tour

Nearly everyone I spoke to recommended the Wendella Architecture River Cruise. You can see a few brave souls pushing through the cold to take it all in. I didn’t have time to squeeze it in (and the cold was a factor) but I will certainly prioritize it next time! I did manage to walk along the Chicago River and it was delightful. The green tint is from the annual green dye they use to celebrate St. Patrick’s day. The boardwalk was so pristine—no liter—and really well designed with lovely wood seating, lighting, and landscaping. Walking along the boardwalk was when I decided I would be back for a warm weather visit.

Local’s Edition

I got way more recommendations than I had time to hit up but that doesn’t mean you can’t! Join the SSBT Chicago Wander Guide to get all the spots via Google Maps.

Coffee

INTELLIGENTSIA

High-end coffee bar chain serving daily roasted brews in an industrial-chic setting.

SAWADA

Chill spot for creative & classic coffee drinks in cozy, rustic-chic digs with Ping-Pong.

Drinks & Happy Hours

BAR LOUIE

Generic happy hour with lots of seating (good for groups).

BLIND BARBER

A speakeasy hidden in a barber shop serving grilled cheese sandwiches.

CITY SOCIAL

Another generic happy hour with lots of seating (good for groups).

EASY BAR

A favorite dive bar with a top notch happy hour every day from 5-7 & an eclectic jukebox.

GILT BAR

Dark and swanky and surprisingly reasonably priced and delish. Get the spicy sausage pasta if you go.

OFF COLOR MOUSETRAP

A favorite brewery in Chicago (and very close to Bebu restaurant).

MONK'S PUB

Great beer—slightly squalid, peanut shells on floor place with German & Old English antiques.

QUEEN MARY

Shaped like a boat and has excellent cocktails.

SCOFFLAW

Cozy gin bar (and right next to Giant if you're trying to do that).

SPORTSMAN'S CLUB

Cash-only hangout featuring a taxidermy theme, table games & a rotating list of cocktails & beer. Has a great patio.

THE DARLING

A cute cocktail bar with a really good happy hour.

THREE DOTS & A DASH

Tiki drinks (flaming options included), 200+ rums & luau bites in a retro Polynesian-island setting. Heard they serve excellent non-alcoholic options.

Restaurants

AVEC

Inventive small & large plates served in a cozy, minimalist space with communal seating.

AU CHEVAL

The burger is worth it— put your name in and get drinks at Lone Wolf next door. If you don't want to wait Small Cheval is related and also great (but not the same).

CINDY'S

Rooftop restaurant. It's touristy but actually great. Be sure to make a reservation.

EDEN CHICAGO

Creative New American fare with Mediterranean influences pairs with craft cocktails in a chic space.

GIANT

Seasonal New American plates & craft cocktails are served in a funky storefront with local art. Pricier and probably need a reservation but delicious.

GIRL AND THE GOAT

Stephanie Izard from top chef's restaurant. Hot spot where Stephanie Izard serves up innovative small plates from a dramatic open kitchen.

GREEN STREET SMOKED MEATS

Hip counter serve dishing house-smoked Texas BBQ & homey sides in woodsy, warehouse like digs.

LOYALIST

Bi-level New American kitchen & bar with casual dining downstairs & tasting menus upstairs.

MOTT ST

Asian-inspired plates & craft cocktails served amid funky furnishings & communal tables.

REVIVAL FOOD HALL

Huge, industrial-chic food court & bar with counter-serve outposts of many popular Chicago eateries.

ROISTER

Chef Grant Achatz’s hip, casual option for creative New American food & drink in lively surrounds.

TABLE, DONKEY AND STICK

Upscale comfort fare & drinks from Europe's Alpine regions served in a rustic, minimalist setting.

Pizza

PIZZERIA BEBU

Seasonal pizzas with thin (gasp!), crispy crusts are offered with beer & wine in a modern storefront.

GIORDANO’S

Known for deep-dish pizza, this casual chain serves other classic Italian food, plus beer & wine.

LOU MALNATI'S

Family-owned local chain for Italian classics & Chicago-style, deep-dish pizzas with butter crusts.

PEQUODS

Casual, brick-walled pizza pub where deep-dish pies with caramelized crusts are served until late. Local’s say this is the only one that’s worth it.

Activities

ART INSTITUTE OF CHICAGO

Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.

SECOND CITY

Known for its many famous alums, this storied spot hosts popular sketch shows & improv classes.

Chicago, you were COLD AF but I loved you!

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