Our 2019 Chicago Adventure - Michelle and Sara Photography

October 10, 2019

Now that the news of Sara’s pregnancy is out, we can finally say that this trip was a special one because of it!

If you have been around here for a while, you will know that Chicago isn’t a new city for us to travel to. It’s a city close to our hearts as my husband (Joe) and I grew up near and around it. After we moved, we still traveled back with Sara and Matt to see family and friends. When Sara married Jake, we went on a 2015 Chicago trip to show him around and boy did he love it!

For this trip, Joe and I were planning on making a small trip up to see some family and friends. When I told Sara about our idea, they asked if we wouldn’t mind them going and of course, we said not at all! Then when Sara announced her surprise to us days before our trip, we knew this was going to be a special one.

*Sara here, quick side note: when planning on coming with them on this trip, I had NO idea I would be pregnant, so there’s that!*

the schedule

Now, let’s give you a quick rundown of our schedule!

Wednesday, 9/18: fly from RDU to ORD, pick up the rental car, go to Gene & Jude’s hot dog to eat lunch, get to Hotel Cass in downtown, then eat dinner at Berghoff.

Thursday, 9/19: eat breakfast at Yolk, walk around State Street and shop, eat Portillos for lunch, go see the Cubs play at Wrigley Field. Oh and also purchase a LOT of cubbies attire then photograph the first announcement photograph. *see below*

Friday, 9/20: eat breakfast at Chicago Waffle and head over to the Field Museum and explore for most of the day. Before we leave, we head down to the docks to take the second announcement photo! Then we meet up my longtime friend, Cookie, for dinner at Gino’s East!

Saturday, 9/21: explore more of the area with shopping at old book stores, eating lunch at Volare’s, and then switching hotels before leaving to meet the family up at Portillo’s for dinner!

Sunday, 9/22: our last full day was a rainy, cold day. We stood close to the hotel, at lunch at Pizano’s, read books in the cafe, ate soup from the Soupbox and snuggled into our rooms for the night.

Monday, 9/23: we leave our beloved city back for home all the while missing the delicious food before even in the air.