Planning a getaway? Check out Chicago, IL, a city bursting at the seams with art museums, parks, architecture tours + a bustling food and drink scene.

I’ll be honest — I visit the Windy City a lot. I’m there at least five times a year to see friends + visit craft breweries. I have the usual spots on my agenda each trip — like Al’s Beef, Marz Community Brewing + Navy Pier — but the best part about getting away to Chicago so often is that it feels new and exciting each time I go.

Why go?

Italian beef. Okay, so there’s more to Chitown than a seemingly never-ending supply of thinly sliced roast beef sandwiches, but they are worth the trip no matter how far away you are.
Chicago is the third largest city in the US, so the museums alone are top notch, but it's also home to 300+ parks and its many neighborhoods are packed with foodie destinations — you have to try Girl & The Goat.
And coming up on the Chicago radar: the Chicago Thanksgiving Day Parade on Thurs., Nov. 24 and performances of “A Christmas Carol” at the historic Goodman Theatre + plan ahead for one of the best St. Patty’s Day celebrations in March — the city even dyes the Chicago River green.
Learn more about Chicago through these 38 essential eateries + explore Millennium Park and sip cocktails at these winter rooftop bars.

Italian beef sandwiches originated in the Windy City.
| Photo by LOUtoday

Act like a local:

Choose from interchangeable categories (suggestions below, Swim: Nightlife: Family: etc.)

Food: The Publican. Inspired by a European beer hall, this restaurant’s menu is pork-focused + features a curated list of oysters.
Drink: Dark Matter Coffee. With eight locations throughout the city this local, innovatie coffee roaster is a must sip — try any of the barrel-aged coffee beans.
Outdoors: Chicago Botanic Garden. Enjoy 385 acres of landscaped gardens + don’t miss its holiday light installation, Lightscape, that lights up Nov.-Jan.
Nightlife: Three Dots and a Dash. Heat things up at this bar set in a retro Polynesian-island with flaming tiki drinks and 200+ rums.
Explore: Color Factory Chicago. Travel through the colors of the rainbow at this interactive art museum.

Where to stay:

Vrbo: Bella Villa on Taylor Street. Complete with three bedrooms + two baths, this second floor flat overlooks “Little Italy.” (~$195/night)*
Airbnb: The Noble Farmhouse. This quiet urban oasis is perfect for returning to after exploring the hustle and bustle. (~$168/night)
Splurge hotel: Chicago Athletic Association Hotel. Located downtown on Michigan Avenue directly across from Millennium Park, this boutique hotel boasts vintage sports-themes, marble bathrooms + it has a rooftop atrium restaurant. (~$349/night)
Save hotel: Aloft Chicago Downtown River North. This stylish hotel chain by Marriott is conveniently located downtown next to eateries + bars. (~$250/night)