Sister’s Weekend in Chicago | By Sasha Elliott
September 26, 2017

Two weekends ago my sister, Kara, and I took our first ever trip solo. Just the two of us — no Mom, no husbands, no babies. Chicago was an obvious choice because it’s a short, cheap flight (and my brother-in-law so generously bought our plane tickets), plus hello, it’s Chi-town. We decided ahead of time that we wanted to stay downtown and ended up with a hotel on the Magnificent Mile. We picked a few things to do ahead of time, but mostly we planned out what we were going to do each morning.

We arrived at about 10 am. Since we were feeling ambitious, we wanted to take the train to our hotel from Midway. Getting a train ticket was a nightmare and we ended up with the nicest Lyft driver! Once we checked in and took a second to plan our day, we opted to grab lunch somewhere nearby. We were both starving so we landed on Emerald Loop — I was particularly happy about this because I ended up being able to get a much-anticipated Pumking beer. If you’re an autumn fanatic, you’ve got to get one of these. It’s like pumpkin pie in a glass. Careful though, this brew by Southern Tier clocks in with 8.6% ABV. Lunch was delightful and just what we needed. By the time we finished, we were ready to go explore the city!

One of our first stops was Millennium Park — aka the “bean.” Kara and I went to Chicago a couple years ago with our mom and other sister, and this was one thing she really wanted to do but we just didn’t do. We knew we had to go this time around. It was gorgeous, of course. We had to snap an obgliatory photo in the reflection of the bean, obviously.


While on our walk around the city, we stopped into the Chicago Cultural Center, which had the most breathtaking stained glass ceiling.

Needing an afternoon pick-me-up, we stopped into Dollop Coffee and treated ourselves to a honey cinnamon latte — I would highly recommend! We took our lattes to go and made our way towards Navy Pier. We had our hearts set on riding the Centennial Wheel (despite my fear of heights). It was such a cool way to view the city!


After heading back to the hotel for a bit, we decided it was time for a glass of wine (isn’t it always?). We opted for City Winery, which is right on the riverwalk. It was such a nice atmosphere and the wine went down too easily.

We ended our fun-filled day with a walk around the city (albeit, mostly because we were lost) and a trip to Target, of course. All-in-all, a great first day of our sister’s weekend.


We started Saturday morning off with a tour of the Frederic C. Robie house. It was designed by Frank Lloyd Wright in the early 1900s. Our tour guide was so knowledgable and the whole staff was super friendly. This is definitely something I’d recommend if you love old houses.


I’m a souvenir junkie, so of course I had to pick up a book and a mug (I collect both). After our tour, we popped over to a cute little cafe called Plein Air for a bite to eat. It was literally right next door to the Robie house and had a great menu.

Also on our agenda for Saturday was a local fabric shop called Oak Fabrics. I had been looking for one to visit on our trip when I saw one of my favorite Instagrammers/bloggers Suzy Quilts mention this shop, so I knew it was the one to check out. I got the coolest fat quarter bundle (the vintage tattoo style Frida Kahlo print is my favorite) and I cannot wait to make a quilt out of it! Before we went to Oak Fabrics, we decided we needed another bite to eat. We saw that Taco in a Bag was on the same block, so we stopped there. It was so good, but you get so much food! We both agreed that we could have easily shared one. On our way to Oak, we also stopped by Half Acre Beer for a pint. Since there was a parade along Lincoln that day, the place was packed! It’s always fun to checkout a local brewery and the beer was delightful. We opted for dinner close to our hotel at Eataly Chicago and took some delicious desserts to-go. The rest of our night was low key and relaxing: dessert in bed at the hotel, face masks, American Horror Story, and a late night snack from Lou Malnati’s.



Our last day in Chicago started off with donuts at Stan’s and a boat tour that focused on the architecture of Chicago. Our tour guide was seriously the best. I will never understand how tour guides can remember so much information and deliver in such a way that’s fun — I can’t say enough great things about her! Our last Chicago activity was brunch (our first of the trip — what?!) at The Kitchen. We both opted for the breakfast sandwich and it was some of the best food I’ve ever had. The view of Clark Street from our outdoor table was pretty great too.

By the time we finished brunch, we figured we’d head to the airport. It was such a wonderful weekend but we were both ready to get home to our boys!


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