Chicago Travel Guide

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

As most of you know, I just returned from an EPIC girls trip to Chicago. I am so excited to be sharing my Chicago Travel Guide with you today. Chicago is one of my very favorite cities, and it was so fun to show my girlfriends around town. I went with my photographer, Shannon, Ariana Lauren and Katie and Samantha from Lola & Ivy. I broke our entire trip down by day. Keep reading to see what we did, what I wore.

Shop Bean Outfit:

Day 1:

Right when we landed, we were starving! There was crazy traffic getting into the city from O’Hare. We dropped off our bags, shot the hotel room (see hotel post here) before we unpacked and headed out for a “snack.” And by snack I mean we went straight to Portillo’s so the girls could experience a Chicago style hot dog. Everyone loved it! Then we went to Garrett’s to get popcorn to snack on during our trip. You can’t go to Chicago without going to Garrett’s. We spent the rest of the afternoon working & unpacking before dinner at Riccardo Trattoria. I have written about this restaurant before — and I go every time I visit Chicago. They always make Cacio e Pepe for me even though it’s not on the menu!

Day 2:

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

We woke up super early on day 2 because we wanted to get photos at the bean with no one else there! We checked what time sunrise was, and headed to the bean around 7 am. It was so early but so worth it! Afterwards, Stan’s Donuts hosted us for breakfast and it was such a nice reward after our early morning! They had so many amazing flavors and we loved that they had delicious seasonal almond milk coffee drinks! Always a win in my book! We probably tried 10 different donuts, and our favorite was the Pumpkin Spice Old Fashioned!

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

After breakfast, we headed to DryBar to get our hair done for the day. Since my hair was already done, we went back to the hotel and shot a couple of outfits.

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

We explored a little bit of the Riverwalk on our way to lunch at River Roast. No matter how many times I visit Chicago, I will never get over the views of the river. San Francisco has nothing like it, and it’s so much fun to walk around that area. Our lunch at River Roast was amazing. We shared the rack of pork and the boatload of veggies. It was so yummy! And the views were gorgeous.

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

After lunch, we went back to the room to work and relax before going up in a helicopter with Chicago Helicopter experience. I will be doing a full post on this so stay tuned for that! We were super tired after that adrenaline rush, so we had a chill dinner at Shake Shack right by the hotel.

Day 3:

You can’t go to Chicago and not take an architecture tour on the river. It was one of my favorite tours I’d ever gone on and I was excited to take the girls! We headed down to Navy Pier to board our Sea Dog Chicago Cruise! It was definitely chilly but so worth it.

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

After the boat ride was over, we explored Navy Pier and got coffee at the cutest coffee shop, The Goddess and the Baker. We were dying to go to 3 Arts Cafe inside Restoration Hardware, so we hopped in an Uber and headed over there. The meal was AMAZING. It was probably the best lobster roll I’ve ever had. I was so hungry that I ate my food before I could take a picture of it. But the restaurant was stunning and we all loved it.

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

Shop Navy Pier Outfit:

 

After lunch we shopped around, made a very long stop at Gucci where I bought my sneakers, and cruised Michigan Ave. We finished off the perfect day with a shoot at the Chicago Theatere and an amazing meal at Bristol Chicago. Their dill monkey bread was probably one of my favorite things I have ever had. I am not even ashamed to say that we ordered every single dessert on the menu. I will definitely be back there!

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

Day 4:

I started off our last full day in Chicago with a workout at Barry’s. I love visiting Barry’s in different cities. This is my sixth studio I’ve been to, and I’m determined to try every single one. This studio is brand new and stunning. I even ran into one of my readers there who started Barry’s after reading this post! It was by far the most touching moment in my blogging career.

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

After Barry’s, we all headed to Lincoln Park to explore. I had never actually been before, so I was really excited to walk around even though it was FREEZING.  We wandered through the conservatory (which was gorgeous) and walked all through the zoo (which is free!). Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

Shop Lincoln Park Outfit:

 

We went to The Allis inside SoHo House for lunch, and OMG. I have never seen a more beautiful space. I could have stayed there all day long! The food was incredible and it was just soooo gorgeous. We all love a good Instagram moment, so we were in heaven.

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

We only had one tourist destination on our list, and time was running out. After lunch, we headed straight to The Skydeck at the top of Sears Tower. The views were insane and standing on the glass was such a rush!

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc. Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

Shop Skydeck Outfit:

 

Ashley Zeal from Two Peas in a Prada shares her Chicago Travel Guide. See where to eat, what to do, where to stay, etc.

After the Skydeck, we met up with my college friend and girl boss, Angie for drinks and dinner. We started with cocktails at Three Dots & A Dash. I have always wanted to come here, and it was so cute. Afterward, she took us to Somerset in the Viceroy for dinner and it was so good! I loved catching up with her!

Day 5:

We chose Hampton Social for our last meal in Chicago, and it did not disappoint. It was the perfect place to end our trip, the meal was amazing and we had the best time reminiscing about our trip. We’ll be back soon, windy city.

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