Great Escapes: Our guide to Chicago, IL

Al’s Beef, Navy Pier, and green rivers, oh my.

October 25, 2022 • 
Katie Molck
The Chicago River flows under a red bridge with skyscrapers in the background.

Chicago is the third largest city in the US.

Photo by LOUtoday

Table of Contents
Why go?
Act like a local:
Where to stay:

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.
A juicy Italian beef sandwich sits on a paper wrapper with a hot dog and fries in the background.

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)