Girls Weekend in Chi Town

A few weekends ago, my mom, sister, and I met in Chicago for a super fun girls weekend. Our plan for a girls weekend originally was that we would go to Bar Harbor, Maine, for some mountains in the springtime. We were flying using Delta Buddy Passes from my Aunt Joan, who works for Delta. For Buddy Passes, you fly standby and the night before our flight to Maine left, it became really apparent that the flights to Maine would be completely packed and we would most likely not get out of Orlando. We tried finding airports that were close by so that we could drive, but nothing looked good.

Finally, we decided to change our plans completely. We were all three packed for cold weather already, so we told Aunt Joan to find us a flight to any cold city. Chicago it was! And I am so, so glad because I hadn’t been to Chicago before and I LOVED IT! We had a blast!

We got into town on a Thursday in the late afternoon and met Ginny at the hotel. We stayed at the Courtyard Marriott Downtown/Magnificent Mile and it was perfect! Just a block of Michigan Avenue and within walking distance of everything. When we were settled into our hotel, we headed out for a first night dinner at Eataly. I had been to the Eataly in New York several times and it was one of my favorites. The Chicago one was just as yummy! We had dinner at the Osteria di Eataly restaurant inside and kicked off our trip with good drinks, good food, and lots of laughing. Since this was a spur of the moment trip destination for us, we spent most of our dinner deciding what we wanted to do that weekend and making a little itinerary.

(Insert picture here of us laughing over champagne and a chartreuterie board that I didn’t take because I’m a slacker blogger.)

The next morning, we were up and at ’em by 9:00. We knew that Friday would be our only good weather day, so we planned all of our outdoor adventures for this day and all of our inside explorations for Saturday. We started with a visit to Millenium Park, home of THE BEAN! Before we headed over to see the Bean, though, we put our names on the wait list for breakfast as Wildberry Cafe. It was a pretty long wait because it is so popular, so we left our name and phone number with them and then walked a block over to see the Bean.

After goofing around with Boomerangs at the Bean, we strolled back over to Wildberry and had a fantastic breakfast! I was going to try to stay pretty keto-friendly on this trip, but then I saw pancakes and that pretty much flew out the window. Totally. Worth. It. Highly recommend Wildberry if you’re in the area! It was delicious!

When we finished breakfast, we were only a few blocks away from the Sears Tower (which is now called the Willis Tower, but I can’t ever remember that, so I still call it the Sears Tower…). It’s funny that this was one of the places on my must-see list for our trip because I am scared of heights. And if I’m scared of them, then my mom is terrified of them. But I was determined to not only go to the top of the Sears Tower, but to stand out in the Skydeck, too!

This is the Skydeck (I don’t know any of these people – I just needed a picture of the whole thing!). It’s a glass box that hangs off the top story of the building, looking down and out over all of Chicago. I have no idea why I was so set on doing this to myself, but I was NOT going to miss this.

So, we paid our $45 and stood in line for 30 minutes and finally it was our turn. Turns out, the glass is not as thick as I expected it to be! I kept telling myself that it was super safe – look how many people go in it every day! But WHOA. It was hard to make myself walk out there! Everyone was like, “Just don’t look down.” And I was totally on board with that. Until I stepped out on the glass and my knees melted away and I sank to the floor, face down to the 140 stories below me.

But I did it! And I was so proud of myself!

My mom, however, was not as excited as I was to overcome her fear. She decided on a very different approach. She was going to sit down on the solid floor and then scoot herself back out on the glass. Which is a solid theory. Except that she physically could not force herself to scoot back. We kept telling her to go further and she was like, “NO! NO! SHUT UP! NO!” I almost wet my pants watching her.

Ginny isn’t afraid of heights and so she tap danced around all of us while we were up there. I almost killed her when she started jumping when the two of us were standing in the box.

With our feet back on solid ground, we decided to continue on with our day. Next up was an architecture boat tour of Chicago, but first… PIZZA. There was a Giordano’s pizza on the same block at the Sears Tower, so we popped in there for our first deep dish experience and it was heavenly!

By the time we left, it was about 3:00 in the afternoon, so we moseyed on down to the Shoreline Architecture Boat Tour. There are lots of boat tour companies on the river, but I had found a Groupon for this one and we figured one was as good as any for us since we were mostly there for the pictures. Turns out, this was a great tour! Our guide was really informative and we learned a lot about the history of Chicago. Not to mention, the weather made this a gorgeous day to be out on the water!

We finished the tour around 5:30 and headed back to the hotel to kick up our feet and decide what to do about dinner. Since we had eaten so late in the afternoon, none of us was very hungry and Mom declared she was getting in bed at 7:00 that night, as is her right on vacation. But I dragged my sister out to the Magnificent Mile for a little nighttime shopping fun!

The next morning it was rainy and colder, which we had expected. The forecast was even calling for snow! We walked around the corner to the West Egg Cafe for breakfast. I loved this place. It reminded me of the diners in Connecticut. It was warm and cozy and bustling with locals. Two thumbs up!

From here, we took an Uber to the The Art Institute of Chicago. I love a good art museum. Especially on cold, rainy, snowy days! It was the perfect place to get lost for a few hours.

The “Artic” has an extensive collection of Monet, Rembrandt, Van Goghs, and so many more. We splurged on the $3 audio tour guide and it was worth so much more! My sister and I got lost in the impressionist wing while my mom stayed cozy in the bookstore. We ended up staying for almost three hours! It was such a perfect snowy morning!

When we finished at the museum, we took another Uber to The Drake Hotel for high tea. WHAT FUN! The Drake is such a famous hotel and it lived up to the hype! So beautiful inside! We spent several hours with our pinkies in the air, eating tiny sandwiches and it was just lovely.

There were so many bridal showers and baby showers being held there, too! And I lost count of how many mothers, daughters, and granddaughters were there together, all wearing hats and white gloves. But there were an equal amount of casually dressed tourists like us, too. Don’t be scared away by the fancy. Everyone should have high tea at some point in their lives!

When we had had enough tea and foo-foo, we decided to end such a girly day with a trip to The Mart. The Mart is a waterfront property in downtown Chicago that is used for all kinds of events. Mom had read that they were having an arts and craft market that weekend called “One of a Kind.” We walked up and down endless aisles of artisan clothing and paintings and foods while a live band played. It was such an unexpected treat on our trip!

We found one booth that had the most amazing hats, so we stopped and played a while. Ginny should have bought every one of them! She looks so good in hats! But, alas, each hat was a few hundred dollars and we just couldn’t justify the cost. Although, the best argument we came up with was telling Ginny’s husband, JM, that it was snowing and she had really needed a hat…

…but in the end, we decided he probably wouldn’t fall for that. 🙂

We finished at the Mart around 5:00 or so and decided our trip to Chicago wouldn’t be complete without a Chicago hot dog. I posted a question on my Instagram stories asking for the best hot dog in Chicago and it was overwhelmingly unanimous that we had to go to Portillo’s and HOLY COW did it not disappoint!

At Portillo’s, you order at the counter and then bring your food to your table. The place is huge and we ended up eating upstairs overlooking the restaurant. Everyone said we had to try the chocolate cake, too. And who are we to deny the people?!?! We had hot dogs and french fries and onion rings and chocolate shakes and chocolate cake and everything was perfection! Keto who?!

On Sunday, we had to be at the airport by 6am, so we ordered an Uber for a 4:30am pick up. That one hurt a little bit. And it turns out that the first flight out was full anyways, so we headed back to our hotel and slept until noon before going back to the hotel and realizing that the snow the previous day had caused a huge backlog of flights and there was no way standby was getting out that day. Ginny flew home on SkyMiles and mom and I stayed an extra night and caught a flight home the next morning.

It was a quick trip, but we packed so much in! And while all of these pictures show all the doing that we did, what you can’t see is all the time we spent talking and laughing and catching up in ways that is hard to do with kids and family and pets and LIFE all around us. It was so nice to stop for a minute and just enjoy my mom and sister for a bit. Our family makes pretty strong women. There’s not a weak one in our family tree. But sometimes, even the strongest women need time to stop and rest and relax and it was so nice to do that with my mom and sister.


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