Weekend in Chicago

Hey there, long time no chat! With good reason though, Jeff and I spent this past weekend in Chicago for his Birthday.

A couple of months ago Jeff decided he wanted to go to Boston for his birthday weekend and we talked about staying to watch the Marathon which was a great idea and definitely something we both want to do but I decided to secretly change the plans on him.

He doesn’t get to see his family all that much so I decided to plan a trip to Chicago instead. It didn’t take to much planning, I just had to make sure his family was available! Jeff’s sister lives there and his parents only live a couple of hours away and conveniently everyone was going to be around that weekend!

So for a couple months I continued to let Jeff think we were going to Boston and whenever he asked details or tried to plan anything I just told him it was taken care of. I finally broke the news to him 4 days before we were leaving, he was excited and we definitely had a wonderful time!

We left bright and early Friday morning getting into Chicago with enough time to drop our stuff at Jeff’s sister apartment, grab some lunch and head to the Cubs game.


We had great seats thanks to Jeff’s sister sharing her company seats with us. We also had great weather. We stayed for the whole game and enjoyed every second of the sun. After the game we hung out for a bit before heading out to dinner.

Saturday morning Jeff’s sister and I headed to a Pure Barre class (you really think I would go away and miss a class?!) After class we headed home to get ready for the day and for Jeff’s parents to arrive. Once they got in we headed to lunch at the Blue Door which was such a cute place! It’s decor was so rustic and exactly how my future kitchen should look!
blue door

After lunch we walked around the Zoo, one of Jeff’s favorite things to do. The zoo in Chicago is free which is nice.



After the zoo we headed to an early dinner at Homeslice (home of the best gluten free pizza I ever had, the crust was FLUFFY believe me, you don’t get that with gf pizza!)gf pizza

After dinner we all parted ways, Jeff’s mom and dad has a concert to go to, Jeff’s sister and boyfriend had plans with their friends and we had plans to meet up with one of Jeff’s friends from high school who recently moved to Chicago. We spent the evening at a bar catching up.

Sunday morning Jeff and I met up with his parents for brunch, window shopping, celeb spotting Bill Rancic and going to the Aquarium (another one of Jeff’s favorite things to do).

After we said goodbye to Jeff’s parents we headed to a comedy/improv show with Jeff’s sister and boyfriend. We saw #dateme, the show was based off OKcupid and one girl who made something like 30 different profiles to see how people would respond to her bizarre characters! It was so hilarious and a great way to end out trip!


Monday morning I woke up to take one last Pure barre class before we headed out of town. We had so much fun in Chicago and it was so nice to spend time with Jeff’s family.

How was your weekend?

Do you have any trips planned?

Have you ever gone to a comedy/improv show? what did you see?

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  • what a fun trip! i’ve never been to chicago but would love to visit sometime, preferably in the summer. that gluten free pizza looks totally awesome. i have never been to a comedy show, sounds like a unique date idea! let’s catch up soon, i want to hear more about the trip!
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