There is something so wonderfully unique about Chicago. Maybe it’s that Chicago has big city appeal paired with Midwest charm. I don’t get the sting of culture shock in Chicago – although the city is much larger than my hometown Cincinnati, the skyscrapers are more spread out so that they don’t close in on you, and it’s still the Midwest, where people are more accommodating. Sure, Chicago is a little dirty, but not compared to other cities of its size, and Lake Michigan is gorgeous in the summer. There are large parks to enjoy, world-class museums to take in, and so much shopping to do on the Magnificent Mile. Chicago is known for its beautiful and diverse architecture, cultural events, and delicious food. Everything about the city is welcoming, and it keeps us coming back for more.
I have so many great memories of visits to Chicago. Every time I visit, I’m reminded of exploring the Magnificent Mile’s toy shops with my English cousins when we were little, enjoying unforgettable meals at our favorite restaurants with good friends over the years, reuniting with my mom and sister at the Peninsula for our first annual girls-only weekend, and, of course, the day that Ryan got down on one knee next to Buckingham Fountain and asked me to be his wife. All of those memories hold a special place in my heart. I’ve never had a bad trip to Chicago.
This holiday weekend was no exception. Ryan and I were so excited to spend the long weekend in one of our favorite places with a few of our favorite people: Ryan’s cousin Andy, his wife Angie, and Ryan’s sister Nikki. This is a ridiculously fun group and we knew we were guaranteed to have a good time. We hit the road right after work on Friday to make the 5 hour drive to Chicago.
Unfortunately, we hit some pretty bad storms on the way into the city, so we were a bit delayed for our late night reservation at BIN 36. Fortunately, we had good company for the drive, and when we finally did arrive we were starving, which really is the only way to approach an evening at this restaurant!
Ryan and I were introduced to BIN 36 by our friends John and Erin. We are obsessed with this place because they boast wine flights AND cheese flights. Why aren’t cheese flights a thing everywhere? We knew Andy, Angie and Nikki would love it as much as we do.
After a long drive, I was happy to indulge in BIN 36’s Italian Treasures wine flight! Featuring wines from all around Tuscany, it was the perfect way to kick off the trip.
We stuffed ourselves with food, then checked into our hotel, the Marriott Downtown Magnificent Mile, and got some much-needed rest.
We woke up to storms on Saturday morning, which was a bit of a bummer, considering we had an 11:00 reservation for Chicago’s First Lady architecture boat tour. Luckily, the rain cleared up just in time!
Nikki had her selfie-stick in tow, which made for a great photo op by the Chicago River before our tour.
Chicago’s First Lady is the official cruiseline of the Chicago Architecture Foundation. Volunteers narrate the tour through Chicago’s river, and every time I go, I learn something new. The volunteers are so knowledgeable – they rattle off so much information it makes my head spin! It’s a beautiful way to take in the sites and learn what Chicago has to offer. Plus, who doesn’t like spending one of the last days of summer on a boat?
After our tour wrapped up we were starving. The only answer for a growling stomach in Chicago is stuffed pizza, and our go-to is Giordano’s. The stuffed Cheese and Meat, Meat & More Meat pizzas really hit the spot!
Supposedly, Giordano’s is coming to Cincinnati – and I. can’t. wait.
We needed to walk off some calories, so we headed towards Lake Shore Drive and took a walk by the lake. The weather had completely cleared up and Chicago was looking gorgeous! Nikki took out her selfie stick and a couple of drunk guys yelled at us – they were pretty jealous of our photography skills.
Walking near Lake Michigan is awesome – even when it is 90+ degrees. Navy Pier couldn’t have looked prettier.
After walking over 20,000 steps, we did some shopping on the Magnificent Mile and then headed back to the hotel for a little break before dinner.
Mercat a la Planxa is one of my favorite spots in Chicago. This restaurant offers the most insane Spanish tapas, and is located inside the historic Blackstone Hotel. This is where Ryan and I ate dinner the night we got engaged, so it is a very special place for us – one that we love to share with friends whenever we can. Since I hadn’t already indulged in enough flights over the weekend (#sarcasm), I followed Nikki and Angie’s lead and ordered the sangria flight, which was absolutely to die for! The rose sangria was my favorite.
The food at Mercat is phenomenal. If you go, don’t miss out on the Datiles con Almendras (bacon-wrapped dates with marcona almonds and la peral – order two of them, you won’t regret it!), Arroz con Morillas (calasparra rice, morel mushroom cream, English peas and asparagus), and patatas bravas (spicy potatoes with smoked paprika aioli). We ordered basically everything on the menu and split it all. We didn’t regret it for a second.
After dinner, we stopped at Ghiradelli for ice cream sundaes, and then took a couple of selfies on the Michigan Avenue Bridge on our way back to the hotel.
Somehow we woke up hungry on Sunday morning. THE breakfast place in Chicago is Yolk, so we walked on over and put our name in for a table. This is one of Nikki’s favorite places to eat in Chicago, and I have to agree with her. I ordered the biggest breakfast imaginable – the Yolk All Star Breakfast – and loved every bite of it. The sausage is out of this world. Next time, I’d opt for the pancakes instead of french toast – I liked them a bit better.
Needing to walk off breakfast, we headed to Navy Pier to take a walk around. It was a gorgeous day. This is a great place to people-watch – tourists from all over the world are here, plus a local or two attempting to get in their morning run through the crowds. It’s nice to be by the water, and you get a spectacular view of the city skyline.
The Ferris Wheel at Navy Pier is worth a splurge if it’s your first visit to Chicago. It’s a fun way to take in the views of the city!
We walked back down the Magnificent Mile and did some shopping by the Water Tower. We had a late reservation booked for Sunday night, so we decided to skip lunch and eat dinner twice.
Eataly is a fantastic new addition to Chicago. Eataly is Chef Mario Batali’s brainchild, featuring a range of Italian eateries and food markets. It is 63,000 square feet of all things Italian food. This is a can’t-miss spot if you’r e foodie in Chicago. Ryan and I visited the location in New York City, but I liked this one better – it’s a little easier to navigate. We grabbed a table at La Pizza & La Pasta for Sunday Dinner: Part 1.
The pizza was divine. It’s the closest thing I’ve had to pizza in Italy – perfectly cooked crust topped with the freshest ingredients. And the cheese! So good. I highly recommend the Verace TSG (the freshest mozzarella imaginable), the Salsicciotta (delicious sausage), and the Massese (Angie and Andy’s pick – a little bit spicy and very flavorful).
After our first dinner, we wandered around Eataly and checked out all the different corners of the market. They have everything from produce to fresh pasta to the most beautiful display of fresh meat and fish.
No trip to Eataly is complete with a cup of gelato. I really enjoyed the Tiramisu – which had full fledged lady fingers mixed in! – and the mint chocolate chip.
We shopped Magnificent Mile a bit more before heading back to the hotel to freshen up and get our game faces on for Sunday Dinner: Part 2. Our reservation was at 10:00 at RPM Italian, Giuliana & Bill Rancic’s restaurant that is very highly regarded. The restaurant was running a bit behind schedule, which gave us a chance to stop by Enolo Wine Bar for a quick drink.
The atmosphere at Enolo is pretty unique, with gold ceilings and eclectic light fixtures. We really enjoyed it and hope to go back there for dinner the next time we’re in town!
We received a text that our table at RPM Italian was ready to go, so we walked back over to the restaurant and were seated at a huge booth by the bar. This place is swanky. We loved the decor! It was packed, even at 10:30 p.m.
This place is a winner. Honestly, you can’t go wrong with the menu, but don’t miss the handmade Cavatelli with pork and beef ragù or the spaghetti and meatballs. Everything we tried was absolutely delicious. This is one of our new favorite places to dine.
RPM Italian gave us the perfect last dinner in Chicago. We can’t wait to go back.
After a late night out, we woke up on Monday morning feeling full and sad to be heading home. We ate breakfast at the Nutella Bar in Eataly, and waited in line for Garrett Popcorn to open on Michigan Avenue (we can’t leave Chicago without Chicago Mix!) We also picked up a couple frozen Giordano’s pizzas, so we have some on-hand the next time hunger strikes.
This trip was even better than we had hoped – it was so fun to spend time with family, and to share places we love and discover new places to go the next time we’re in town. We can’t wait for our next trip with Andy, Angie and Nikki! It’s sure to be a blast.
How was your holiday weekend? Did you eat as much as we did?
Until next time,