Chicago is a great place for a girls weekend and there are a multitude of day and night activities to entertain you and your best girlfriends while in the “Windy City.” There are five main components of a Chicago weekend away with the ladies that I recommend you take part in to ensure a fun and memorable time.
Chicago Girls Weekend Accommodations: Where to Stay
A great area to stay for a girls trip in Chicago is the Magnificent Mile, which is full of top-notch restaurants and shopping, plus close proximity to Lake Michigan and other historic sites.
My recommendation: The Drake Hotel
The Drake Hotel is a historic building that was beautifully restored when Hilton bought the property. It still retains a charm reminiscent of Mad Men glory days while offering top-notch amenities.
Chicago Girls Weekend Accommodations Tip: If staying at the Drake, ask for a one of their rooms with two queen size beds and TWO bathrooms – makes getting ready for your girls night out much easier.
Chicago Girls Weekend Shopping: Where to Hit
The area on and around the Magnificent Mile has everything from designer stores such as Louis Vuitton and Chanel to budget friendly meccas such as H&M and Forever 21 – and every type of shopping in between.
My recommendation: TopShop and the American Girl Place
TopShop: This European institution only recently made its way to the U.S. and only has shops in the states in Chicago, NYC, and Las Vegas. Shop here for trendy outfits and staples with a twist – your wardrobe will immediately have some Euro-flair.
American Girl Place: Even if you don’t have daughters to shop for, an amble through this store will have those of you who had the dolls growing up reminiscing and those of you who are new to the American Girl doll obsession in awe. Row after row of dolls and accessories line the store. Head upstairs to see the doll beauty salon, doll hospital, and American Girl Cafe which has special seating at each table for the dolls. The store also may have you asking your friends: “Do you think my husband will put me in the loony bin if I come home with an American Girl doll – for myself?”
Chicago Girls Weekend Shopping Tip: Decide before heading out to shop til you drop how long you all want to spend shopping and where you want to shop and then compromise. That way everyone goes where they want and you don’t need to worry about one person of the group getting annoyed because you’re all shopping so long.
Chicago Girls Weekend Eating: Where to Dine
Chicago has a lot of high end restaurants, but where you’re really going to have a memorable time is in the hot dog and deep dish pizza shops. If you’ve been friends since your school days, gossiping over hot dogs with all the fixings or pizza oozing cheese and toppings will bring you back to your high school and college days when you couldn’t afford to eat out at fancy places and ate midnight pizza on the floor of your room.
My recommendation: Giordano’s and Portillo’s
Giordano’s: As one of Chicago’s most famous pizza places, the thing to get here is the restaurant’s famous Chicago stuffed pizza, which boasts inches of toppings and cheese on a thick and delicious crust.
Portillo’s: This is a bit of a walk from the Magnificent Mile, but well worth it. Order the Chicago-style hot dog and be prepared to be amazed – and possibly surprised that it doesn’t come with ketchup. Instead, you’ll find mustard, tomatoes, onions, peppers, and a big slice of pickle on top of your dog.
Chicago Girls Weekend Eating Tip: For breakfast or lunch, find a restaurant that offers street side terrace seating for some prime people watching (and to enjoy the outdoors if it’s not winter) or a place along the lake to enjoy a scenic view.
Chicago Girls Weekend Nightlife: Where to Drink
The Magnificent Mile has great places for going out during a Chicago girls weekend because you can find places where you can actually talk and hear each other – especially important if you and the girls haven’t seen each other in awhile – or clubs if you’re all eager for a night of dancing.
My recommendation: Whiskey Bar: Lounge seating in a central location serving creative cocktails plus a decent wine and beer list.
Chicago Girls Weekend Nightlife Tip: To find some of the most popular and hip clubs in Chicago, you’ll want to take a taxi ride to the River North neighborhood.
Chicago Girls Weekend Personalization: Where to Find the Memories
Part of the key to a fun and memorable girls weekend is making it your own. Part of the way to do this is to bring mementos from your friendship, such as funny college videos or photo albums. If you don’t have that, make it a mission to take fun and goofy pictures and then use a photobook website such as Shutterfly to create a mini-photobook of your super fun Chicago girls weekend.
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.