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Chicago Girls’ Weekend

Quality time is a must with your girlfriends! I love when we can get together and just catch up on life! A busy weekend full of delicious food, scrumptious coffee, crafty drinks, and fun entertainment is the best recipe for a girls weekend away!

Day one:

Meet at Virgin Hotels at 9 am and drop off your bags at the front desk. They should hold them for you until you can check in!

Head to Hero Coffee on E. Jackson Blvd to grab some delicious coffee and a snack. This location is actually pretty cute and in an alley! It’s also not too far from the Art Institute of Chicago, where you’ll spend the next couple of hours looking at all the beautiful artwork.

How cute is this coffee shop?! Photo credit:

Then head to the Magnificent Mile for some shopping!! When we go we especially like to hit up Eataly and Saks on Fifth Ave. My all time favorite it Nordstrom Rack! While you’re there, grab a late lunch and an afternoon pick me up at the Grand Lux Café. They have some of the yummiest desserts and drinks!

Go back to your hotel to officially check in and freshen up. You’ll want to change for the theatre. One perk of staying at the Virgin Hotels is the free cocktail hour every evening from 6-7pm. Take advantage of that while staying! Head up to Cerise, the rooftop bar, before leaving around 7. The timing of the sun setting should be perfect; just think of the beautiful views of the city!

Most likely your play will be at 8 so you’ll want to get to the theatre no later than 7:45. It’s only a 5 minute walk to the Oriental Theatre; basically right in the theatre district of Chicago! You can find a list of all the shows going on here. Enjoy your show and the next couple of hours sitting (after all that walking around the city!).

My view when we went to see Hamilton last year! I’ve seen quite a few shows, but this one is a must see show!!!

After your show, walk to Mr. Browns Lounge. This restaurant / bar is known for it’s authentic Jamaican dishes. My girlfriends and I always like a fun adventure with our food, and we love trying new things! The atmosphere of Mr. Brown’s Lounge looks like a lot of fun! After 10 pm they serve late night meals (not the full restaurant menu). However, the late night meals are perfect for sharing, and I’m sure you’ll be hungry after a long day of walking! May I suggest the Jamaican jerk wings, island style mac & cheese, fried plantains, and waffle fries.  And we can’t forget drinks: how about the Island Rum Punch or The Mr. Brown!

If you’re feeling up to it, head back to Cerise. There is music and entertainment throughout the summer!

Day 2

Sleep in! Make brunch reservations for 10 am at 3 Arts Club Café! This brunch restaurant looks AHHHMAZING! Their truffle grilled cheese and their hand cut fries look so delicious, as well as their chai tea. And I love that they have cold pressed juices! You’ll most likely want to Uber there as it’s a 30 minute walk, and if you drink the night before, well let’s just say walking that much before breakfast may not be the best! 😉

Photo Credit: 3 Arts Club Café Website

Pick up bikes at the Divvy Station located at Ritchie Ct & Bank St, just a few blocks from 3 Arts Club Café. (You can rent them for 30 minutes at time or for a solid 3 hours.) Follow the Lakefront Trail along Navy Pier to the Buckingham Fountain. Make sure to go to Milton Lee Olive Park to enjoy some harbor views with the city in the background. Bike to the Millennium Park Divvy Station to return bike and walk to the famous Bean for some fun and photos! From there it’s a 10 minute walk back to the hotel. *Be sure to grab an ice cream cone at either Original Rainbow Cone on Navy Pier or Royal Scoops Ice Cream by Buckingham Fountain for a refreshing summer treat!

* Milton Lee Olive Park* I took this a few years ago during an engagement shoot! The views were gorgeous!
Buckingham Fountain!
The famous Bean!

Take a few minutes to freshen up or rest in your hotel room. I would do an early dinner as you really only had brunch and ice cream! Plus Miss Ricky’s Diner closes at 6 and you do not want to miss out on this diner’s food! I would make reservations for 5. After dinner there is a free cocktail hour from 6-7pm offered for guests of the hotel. Again, take advantage!! 🙂 Head up to Cerise to see what entertainment is going on. Grab another drink and enjoy the night and views!


Day 3

After getting ready for the day, drop off your bags at the front desk. They should hold them for you. Then head down to Two Zero Three Coffee Bar in the hotel. Uber to the Museum of Science and Industry. They often have special exhibits throughout the year. My friend and I went just for the Charlie Brown Exhibit one year! Walk to Plein Air Café for lunch around 11:30ish. Then head to the Garden of the Phoenix, a beautiful Japanese Garden.

Charlie Brown Exhibit at The Museum of Science & Industry

Garden of the Phoenix: I mean how beautiful is this place? Photo credit: Network For Good

Then walk to the Promontory point for some lake views! You might as well soak up as many gorgeous views while you’re here!

Promontory Point – photo credit: Pridezillas

Afterwards walk to the 57th Street Books to check out their selection of books!  My friend and I spent an hour or so just browsing their books… we we’re in book Heaven! Then head to Medici on 57th for an early dinner. This restaurant / café has such a variety to choose from! After dinner head back to the hotel to pick up your bags and head home!

*If you have extra time before the Promontory Point, you could walk to the Stony Island Arts Bank. It’s a hybrid gallery with a variety of items to look at.

In addition to this, if you’d rather not do the museum / café day you could do a day in Andersonville on a Sunday (for day 2) and move the original day 2 to day 3. Andersonville is a neighborhood north of the loop. It is a Swedish neighborhood with thrift shops and vintage items. They also have the Green Mill Cocktail Lounge, a popular Jazz bar. Some ideas for the day there: brunch at Pastoral Artisan Cheese, Bread, & Wine, Brown Elephant thrift shop, Andersonville Galleria, Women & Children First bookstore, George’s Ice Cream and Sweet’s, Middle East Bakery & Grocery to taste some Middle Eastern spices with hummus and pita bread, Wooden Spoon, Hopleaf or Big Jones, and Uptown Poetry Slam at Green Mill Cocktail Lounge.

Much love,

Chef Charley


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