Chicago

Where: where to stay
We stayed at the Trump Hotel located near the beach. Trump International Hotel & Tower is in Chicago's River North neighborhood which connects to different sides of the city for easy navigation and walking distance to all the must see sites of Chicago.

When: We went near the end of May and the weather was a little all over the place. Started off windy with a slight drizzle to sunny and warm. I would suggest checking the weather prior to packing since the weather changes on a dime. The saying “don’t like the weather, wait 20 minutes” rang true for us so packing layers is a must!

What : what to pack
cross body purse, comfortable walking shoes (wether that be sneakers or sandals), layers! : tanks, tees, light jacket & heavier jacket, umbrella depending on the month you go!

What: what to do
We started off our trip with the Architecture Boat Tour, definitely a must! Be sure to do the river & lake tour to get the most of your tour and to see the entire city view! This was such a perfect way to greet Chicago and the start of all of the yummy food & drinks we had on our trip.

We took the kids on this trip so finding family friendly activities was our mission and Chicago didn’t disappoint! We took the kids to the Field Museum to see Sue the largest t-rex ever found in the US as well as the other amazing exhibits they offered. I wish we would have planned 3 hours for the Field Museum but we were able to see a ton in the hour and a half we were there. The Shedd Aquarium was on our list but tickets were sold out when we arrived. My suggestion would be to buy tickets online ahead of time to be sure you get in! There were so many options for museums, the Chicago Children’s Museum was also on our list to see but didn’t get to.

For the best views of the city, there were so many options! We ending up picking the 360 Observatory at the John Hancock Tower. Buying tickets ahead of time was another MUST… also, be ready to wait! We waited over an hour in line to take the elevator up but the view made it all worthwhile. At the top, we bought souvenirs, had a few cocktails, and took in the views. The kids were pretty hungry at that point so it was nice to be able to walk down to Bennnihanna’s for a yummy dinner & show from the chefs.

We really enjoyed walking all around the city and checking out all of the best rooftop bars & restaurants. If I had to pick one CANT MISS restaurant from our time there, it would be the London House Rooftop Bar just across the street from the Trump Tower. It had great drinks and appetizers, enjoyable views, and the convenient location didn’t hurt!

Obviously, you can’t go to Chicago without visiting the Bean & the children’s park which were both an easy walk from our hotel. The park had more than 3 jungle gyms for the kids which Abel & Royce were all over. During our trip the Bean was fenced off due to the pandemic. If you saw my Instagram photo with the Bean you’ll notice I was able to get a shot without the fencing in it. If you are as dedicated to the craft as I am (lol) here’s how to get that shot: walk around the south side of the Bean, through the trees theres a wall there. You’ll climb up and shimmy on down that wall until you have the Bean directly behind you. Your photographer will have to raise the phone up high, and there you go! Proceed with caution (lol).

The highlight of our trip was getting to go to a baseball game at Wrigley Field! We bought tickets for the Padres vs Cubs game before we even had our flights booked. Our seats were behind the 3rd base line and they were great! Highly suggest getting to the area a few hours early to enjoy all of the fun restaurants and bars buzzing with excited fans. If you are looking to get a picture in front of the infamous Wrigley sign, I suggest doing so at least an hour before the game starts to lower the amount of photo bombers (lol).

As for food: Oh my, I need to do a second blog post just on all of the amazing restaurant options + the incredible Chicago dog (you’ll never eat a hot dog the same way again)! We enjoyed so many random places we just ducked into like The Green Mill (which is where Al Capone was known to hang out in his day) & STK steak house! We honestly didn’t have one bad meal the entire trip no matter which area of the city we found ourselves!

With Chicago’s endless options, planning our trip was honestly a little overwhelming. There were so many things we didn’t get to do like Navy Pier, Magnificent Mile Shopping, and more. For us, 6 days and 5 nights were not enough. We are definitely looking forward to a second visit!