How to Plan the Ultimate Chicago Weekend Getaway

Sahar Enady February 21, 2021

0 2 minutes read

If you are in need of inspiration for a fun-filled, exciting weekend away, then look no further than Chicago. The Windy City, in fact, offers plenty of great opportunities to those who are even just passing through for a few days.

Keep on reading to discover how to organize the best Chicago weekend getaway. We’re going to give you the lowdown on the most interesting things to do in Chicago so that you have an unforgettable trip.

Start the Day With Some Culture

If you are a lover of art and culture, then Chicago is the right place for you. With its many art galleries and cultural centers, you will be so spoilt for choice that just a weekend might not be enough!

If you’re pressed for time, make sure you don’t miss the Art Institute, the McCormick Gallery, and the Chicago Cultural Center. You’ll be able to enjoy some incredible permanent collections and temporary exhibitions that will absolutely wow you.

Have Lunch (or Brunch) at One of Its Amazing Eateries

Calling all foodies! Chicago is a great destination for those of you who appreciate great, varied, and exciting cuisine. For a lunch or brunch, you could opt for Lou Mitchell’s diner, or pay a visit to The Village.

Fancy a pizza, for a quick but delicious midday meal? Then you must not miss Giordano’s and Lou Malnati’s. And if you get lucky with the weather and would like to eat outdoors, then an absolute gem is Blue Door Kitchen & Garden (if you decide to go there, make sure you try their famous hummingbird cake: Oprah’s favorite!).

Afternoons Are for Exploring the Outdoors

A good, long walk is just what you need to burn off that yummy meal that you’ve just had, and Chicago offers lots of options that won’t disappoint. You could either go for a stroll around the Loop (Chicago’s Downtown) or explore the great outdoors surrounding the city.

A great idea is to try a canoe or kayak trip on the Chicago River or, if you prefer something a bit less adventurous, you could rent a bike and go for a cycle around Jane Addams Memorial Park. Visiting in the summer? Then a dip in the lake is a must.

Get Ready for a Party Like No Other

You’ve ticked off culture, food, and outdoor activities, so what’s left now? Nightlife, of course. If you thought that New York is the only city that never sleeps, then you might want to think again.

Chicago is a night owl, too, with a vibrant and diverse scene. Visitors who enjoy comedy clubs will find plenty of options to have a laugh, while music fans will be seduced by the city’s many clubs and live music venues.

Looking for something a bit more fun and edgy? Then why not try a booze cruise?