A big city like Chicago is a great location if you are planning a girl’s weekend trip. Sometimes you just need the time to get away from the realities of life and while we all love our families and significant others, sometimes you just have to have the escape of having a few days to yourself with just your girlfriends. Depending on the time of year, be sure to prepare because in the colder months of the year Chicago can get to be pretty chilly, and even in the warmer months, it isn’t called the Windy City for nothing, be prepared for those windy conditions! Here are a few of my top picks for things to do and places to stay in Chicago.
West Loop: A Foodie’s Dream Spot
The West Loop is an old meat-packing industrial area that has been transformed into a spot filled with modern and delicious eateries making it home to some of the most popular restaurants in Chicago. You can explore the West Loop with the help of a local through the Chicago Greeter program, a free guided tour that will take you through the best shops, dining, and attractions in the area.
Where to Stay in the West Loop:
There is not a shortage of places to stay near the West Loop by any means but some of the best-rated and most popular choices include Crowne Plaza West Loop, the Hampton by Hilton West Loop, and The Emily Hotel, which provides a more unique experience as it is inspired by a west coast way of living filled with beautiful art inspired by nature.
Where to Eat in the West Loop:
As I mentioned, the West Loop is a hot spot for dining, so there are endless options of amazing restaurants and foods that will fit whatever you are craving. There is an area in the West Loop on Randolph Street that is known as Restaurant Row. Here you will find some of the most well-known spots in Chicago including Nobu Chicago, Forno Rosso Pizzeria Napoletana, and Girl and the Goat.
South Shore: Arts and Relaxation
The South Shore offers an area for those that love the beach and enjoy the art around them. South Shore houses one of the largest beaches in the city of Chicago making it a great way to spend a relaxing day during the Summer months. South Shore is also a hot spot for the arts whether that be through art pieces, theater performances, or even music. You will find places such as Stony Island Arts Bank, The Quarry Event Center where you can enjoy live music, and the ETA Creative Arts Foundation.
Where to Stay in South Shore:
There is a lot of variety in places to stay near South Shore, you can find higher-end places as well as those that are more affordable and considered bargain lodging. If you’re looking for something a little nicer but may be a bit pricier on a nightly basis I would recommend the Best Western Plus Hyde Park or the Hampton Inn Chicago-Midway whereas some options that are a bit more affordable include the Chicago Lake Shore Hotel or the McCormick Place Guest House.
Where to Eat in South Shore:
There are a few options for dining near South Shore for you to enjoy. If you are looking for a dine-in experience a couple of great choices include Mary Jane Café or The Foodie Spot. If you are looking for something grab n go perhaps that you can take to the beach with you, Slab BBQ is a great choice. A fun fact about all of these restaurants is that all are both women and minority-owned so not only are you getting some great food options, you are supporting small businesses as well!
Ravenswood: Perfect for those that love breweries and taprooms
Ravenswood is a hot spot for those that love trying craft breweries and spending their time in taprooms. If you love craft beer, then you will fit right in with the Chicagoans and Ravenswood will definitely want to be on your radar. Ravenswood is home to “Malt Row” where you will find popular microbreweries including Begyle Brewing Company, Empirical Brewery, and more.
Where to Stay in Ravenswood:
A lot of the neighborhoods in Chicago are very close to one another so there are a lot of hotel options that will be accommodating to multiple areas of the city. If you are looking to spend a lot of your time in Ravenswood a few popular choices for lodging include the Hampton Inn Chicago North, Best Western Plus Hawthorne, and The Guesthouse Hotel.
Where to Eat in Ravenswood:
While some of the breweries and taprooms also serve food so you can eat while you enjoy your beer, there are some great options for simply dining in Ravenswood as well. Some of those include Bayan Ko where you can find some incredible Cuban food, Spacca Napoli is great for enjoying pizza, and Taqueria El Asadero is a great choice if you are craving Mexican food.
Notable experiences and attractions:
There is so much to do in Chicago and you can’t possibly mention everything so I just wanted to include a little snippet of some famous attractions and experiences for you to consider adding to your agenda for your trip. Some can’t-miss activities include shopping on the Magnificent Mile, the Navy Pier, Millennium Park, and of course catching a Cubs game at Wrigley Field.
Chicago has so much fun and adventure to enjoy. The city fits wide a variety of personalities and friend groups which makes it a very versatile destination. Chicago can be a quick drive for those in the Midwest or central areas of North America and a fairly affordable plane trip for those that may be too far to drive. If you are planning a girl’s trip for your friend group in the future, I hope that this may have you considering Chicago as your destination.
Lucky you living in Chicago. I love the city so much. The Drake is such a cool hotel and they have some great bars inside, too. Hope you get a chance to check it out sometime soon!
It’s crazy that I’ve lived here for 4 years and still haven’t visited the Drake. It’s such a historic venue and I keep meaning to do it. Sounds like you girls had a great time. I’m making plans to get over there ASAP.