Weekend trip to Chicago

This weekend Cory and I took a super last-minute trip to the Windy City of Chicago! I’d never been before so it was on my bucket list for a while! We planned the whole trip less than 48 hours before our plane took off, but it all turned out perfectly and Chicago did not disappoint. I’m not sure what I was picturing, but it was SO much more beautiful than I expected.

As soon as we landed we headed to our hotel, The Waldorf Astoria, which was simply gorgeous. The hotel staff were all so nice and helpful and our room was even ready 2 hours early!

When we left the hotel, our first stop was lunch at Cafe Ba Ba Reeba, which is Spanish cuisine. We ordered so many yummy Tapas, which are basically small appetizer dishes. This place was SO good and was probably our favorite from the entire trip.

Goat cheese baked in red sauce
Beef tenderloin with blue cheese
Garlic grilled shrimp

Next, we got some fun drinks on the 94th floor lounge of the John Hancock center!!! It had the most amazing views!! This picture was taken in the women’s bathroom. I mean, seriously… have you ever seen a bathroom with this kind of view?

Next, we explored the Magnificent Mile (a pretty, upscale shopping street) and then went to dinner at RPM Italian, which was super cute and had great food. On our way to the restaurant, we passed a taxi advertisement that said “Aladdin… Now Showing,” so we instantly looked it up and bought some affordable tickets to a showing that same night!

Our Uber driver struggled to find us on the busy Chicago streets, but once he finally did, we headed to the Cadillac Palace Theater. I absolutely love musicals and was so excited to see one that I’d never seen before. Aladdin is also one of Cory’s favorite Disney movies so it was a win-win for both of us. The show was awesome and I’d definitely recommend it to anyone visiting Chicago.

Saturday morning we woke up early for a breakfast reservation I made at Little Goat Diner. The Diner was started by Stephanie Izard, who competed and won on Bravo’s Top Chef TV show. She has a couple other restaurants in Chicago, but apparently you need to make a reservation a couple of months in advance to get a table! This restaurant was fun and had some quirky things on the menu. Cory got Chicken & French Toast (as opposed to Chicken & Waffles) and I got the “Fat Elvis Waffles,” which had bananas, peanut butter butter, and bacon maple syrup! They were DELICIOUS! We were tempted to try a dessert called “Cheeze-It” just because it sounded interesting but we were too full after our meals. Tell me you’re not intrigued when you hear what the description of this SUNDAE is: cheez-it and strawberry gelato, chocolate covered cheez-its, milk chocolate, strawberry sauce, and whipped cream. We will definitely be saving room for that next time!

Then we went to the iconic Willis Tower to see the gorgeous views of the city from the Sky Deck and stand on “The Ledge.” If you haven’t heard of the ledge, it is a glass balcony extending a few feet outside of the 103rd floor of the tower. It was an extremely weird feeling stepping onto the clear balcony over the city and we were both kind of nervous, but ended up trusting the glass balcony and even did a jumping photo!

After we rode the elevator 103 floors back to the ground we got on a double decker hop-on hop-off bus to see more of the city. We eventually ended up back at the Magnificent Mile and did a little more shopping. Of course we also had to try some deep dish pizza so we stopped at Pizzeria Due for lunch. Cory loved it, and I thought it was pretty good, but I think I still prefer Domino’s. Haha… just being honest!

That night we walked around our hotel a little before going to dinner at Lyfe Kitchen and then for dessert at Amarino.

Flower shaped gelato cones

Overall, it was such an awesome trip!! We were only there for the weekend, but I felt like we got to do everything we wanted to do!! I love exploring new cities and can’t wait to pick our next destination. Where are your favorite places you’ve been?

Amy Cotton

Join The List


  1. Wow Amy! Your trip looks magnificent. I haven't been able to travel with my husband since our daughter was born in 2014…looks like we need to plan a trip soon!

  2. This makes me smile just to see your happy faces in Chicago! We live two hours east of there and try to get to the city several times a year. We stayed at the Waldorf once and it was great. Those gelato cones, oh my! You two are the cutest, great pictures!

Leave a Reply to Heather Bramlett Cancel reply

Copyright © 2017 · Theme by 17th Avenue

%d bloggers like this: