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If you’re debating on a girls weekend in Chicago I’m here to tell you to just go ahead and book it now! Chicago is the best spot for a weekend with girlfriends. Whether you’re a foodie, shopaholic, or just wanting to sit back and relax there’s something for everyone. I recently planned a girls weekend in Chicago with one of my girlfriends but plans changed and I ended up going with my mom instead. And let me tell you, it was a trip to remember!
We stayed pretty close to the Magnificent Mile (Michigan Ave) for the majority of our trip. What I love most about Chicago is that the city is so big but it’s also very walkable. When you’re walking from one location to another there’s almost always something else to see or do along the way too. So definitely keep room in your itinerary for just exploring. But let’s get started… Here’s a breakdown of how we spent two days in Chicago.
While our accommodations were compensated all opinions are always my own.
Where We Stayed
We made the Radisson Blu Aqua our home base during our stay. And it was one of the best hotel experiences I’ve ever had if I’m being honest! The room was spacious and very clean (which is the most important factor for me). We stayed in the Executive Room on the 18th floor. The entire room is also made up of floor to ceiling windows and includes a wrap around balcony so the views were second to none. And the hotel’s location was also perfect, sitting right in between Millennium Park and Chicago’s Riverwalk. We were able to walk to most of our locations the entire time!
A few of the amenities that’s also included:
- Free WiFi
- An 8,000 sq ft. fitness center
- Indoor and outdoor pools
- Steam and sauna room
Our room was so cozy that we made it back every night by 6pm just to relax and unwind and enjoy the views from our balcony. We even made sure to hit up the hotel’s on-site restaurant, FireLake Grill House & Cocktail Bar, on our second night there. It’s open daily from 8am-11pm so it’s always a great dining option if you don’t want to leave the hotel (or change out of your comfy clothes).
Now, let’s get to the itinerary!
Day 1
Morning
For breakfast, head to Venteux’s cafe. This little Parisian-inspired cafe is the prettiest dining spot we visited during our trip. Finding an open table might take some patience as this is a very popular spot but rightfully so. Get the Venteux breakfast or avocado toast. The portions are just enough to fill you up, which I wasn’t expecting. We also just had to order the chocolate mousse cake because it was calling our names. And we are so glad it was. Let me tell you… Cake at 9am tastes so much better!
Then, stop and grab some pon de ring donuts (aka mochi donuts) and a strawberry latte at 2d Restaurant. And be ready to take so many photos because this restaurant was made for great photo ops! We had a chance to talk to the owner, Kevin, who opened the shop with his wife. They combined their love of coffee, comics, and Emily in Paris (which I am obsessed with) to create this unique space. Each drawing also has a meaning or story behind it so pay attention to every detail!
On your way back down to downtown make stop at North Avenue Beach. Sit back, relax, and enjoy the beautiful views of the city skyline. This is another perfect spot for a photo op.
Afternoon
Grab lunch and the most Instagrammable shakes at JoJo’s Shake Bar. Topped with the yummiest treats like cotton candy, giant marshmallows, and even chocolate CAKE, you really could just share one between 2-3 people. Visit the River North location and reserve a spot in the outdoor seating to immerse yourself in JoJo’s Candyland. My mom ordered the miniature hot dogs and I had JoJo’s fries (topped with mozzarella, provolone, cheddar, bacon, chives, and sour cream… SO GOOD!).
Then, take a walk around Michigan Ave. Shop til you drop and try different snacks along the way. One of my favorite foods to grab on-the-go is Wow Bao at the Water Tower mall location. The teriyaki chicken baos are amazing! But if you’re a bubble tea connoisseur like me, head to The Shops At North Bridge to grab an organic boba drink at TE’AMO Boba Bar.
Evening
Head back to the hotel to relax after all of that walking and get ready for dinner at the on-site FireLake Grill House & Cocktail Bar. Ask for a fruity mocktail (or cocktail if you want) and let the waiter surprise you! Also, go for the 2lb pretzel and thank me later.
That wraps up day 1!
Day 2
Morning
You can’t visit Chicago without visiting The Bean! Head out early and walk down to Millennium Park to visit Cloud Gate, aka The Bean, for some obligatory photos. Since this is such a popular spot I found that it’s best to get there before 10am to get a photo without much of a crowd in your shot.
For breakfast, walk north a block to Stan’s Donuts or Nutella Café (or both!). Both of these cafes are super cute and offer some sweet breakfast options.
Then, see Chicago from a different view and visit one of the observation decks. If you’re looking to just enjoy the view with a cocktail in hand then head to 360 Chicago. They have a stocked bar and some really good drinks to try! We hung out for an hour just watching Chicago from all different angles while sipping on some Bloody Mary’s. They also have a ‘thrill ride’ called the Tilt that offers downward facing views from the top. I personally love a good thrill and found it to be kind of anticlimactic.
If a good thrill and amazing photo op is more your jam then head to The Skydeck and take a step out onto The Ledge. I personally prefer this experience to 360 Chicago, but they both have something great to offer!
Afternoon
Nothing says girls weekend in Chicago like boat ride! Take a ride on one of Chicago’s boat tours. While we weren’t able to snag tickets in time we have heard the most amazing reviews on the Chicago architecture river tour. We’ll be sure to hit that next time! Instead, we were able to admire the architecture and grab lunch along Chicago’s Riverwalk. Again, another beautiful spot for a photo op. This city is just filled with them!
Evening
Hit a rooftop bar and restaurant for dinner and soak in more views of Chicago from a different angle. We visited Cindy’s rooftop and enjoyed a mocktail (which were amazing) but found the atmosphere didn’t quite meet our expectations (or maybe our waitress was just having a stressful day). I had a few local Chicagoans reach out to me after the fact and give me a list of their favorite rooftops including:
And there you have it! That sums up our girls weekend in Chicago! There is so much to see, do, and eat in Chicago that one could easily spend a week here trying it all. If you’re headed to Chicago with your girls soon have so much fun! I promise you won’t be disappointed.
For more itineraries on some of my most recent trips check out my blog posts here.
Sincerely,
Savanna
