I finally made it to the Windy City!

My first time visiting Chicago was a weeklong adventure of eating our way through the city and visiting the plethora of attractions. The trip started off a little rocky as our flight was delayed by several hours but eventually we were off. Typically I don’t make reservations on the day I arrive anywhere in case of travel disruptions but this time I did (rookie mistake). We had to go straight from the airport to our dinner reservation at Monteverde Restaurant & Pastificio which wasn’t ideal but we made the most of it!

We stayed at the Viceroy Hotel which was in prime location, had a small gym, and a rooftop bar with an awesome view of the city.

Our first day started off with getting breakfast at Ann Sather, a diner style restaurant known for their cinnamon rolls. The restaurant was packed (to be expected on a weekend) but we just got a few rolls to go (pecan roll and cinnamon roll). So warm, fluffy, and delicious!

After the scrumptious rolls we walked past Wrigley Field and then through Lincoln Park, a picturesque park which also has one of the country’s oldest free zoos.

During our walk back to the hotel, we came across the original Playboy Mansion which was built in 1899. The mansion was purchased by Hugh Hefner in 1959 for $400,000 and became a party palace with its iconic bunnies in the 1960s and 1970s. Eventually, the mansion was converted into luxury condominiums which are now worth millions of dollars.

The Original Playboy Mansion.

Once we returned back to our hotel, we relaxed before our late dinner reservation at Alinea for a once in a lifetime dining experience.

The following day started off at Pequod’s Pizza, one of the most well known restaurants for deep dish pizza. Be sure to make a reservation because this place fills up quickly and the pies take around 30 minutes to cook. People might argue that this isn’t traditional deep dish pizza because of its crispy cheesy crust instead of the thicker baked dough crust but it was phenomenal. We got half pepperoni and half meatball with onions and it was so scrumptious.

We spent the remainder of the day mostly at The Field Museum of Natural History, one of the largest museums in the world. The highlight was definitely the Egyptian mummies on display, so cool!

Right next to The Field Museum of Natural History is the Shedd Aquarium. The aquarium is known for the oceanarium, the largest indoor marine mammal facility in the world where you can see various marine mammals such as white sided dolphins, beluga whales, sea otters, and sea lions.

After a day at the museum and aquarium we got a sweet afternoon snack at Firecake Donuts.  We got the vanilla iced glazed donut and orange poppyseed old fashioned donut and the old fashioned donut was surprisingly the winner.

This night we didn’t have dinner reservations but we had planned to go to Au Cheval, the famous burger spot that numerous friends recommended. Unfortunately they don’t take reservations so waiting is inevitable. We put our name down and went to a nearby bar where we waited for almost an hour but the wait was totally worth it.

Kale Caesar with Garlic Sourdough Crumbs.

Crispy Fries with Mornay Sauce, Garlic Aioli, and Fried Egg.

The Famous Burger with Added Bacon and Egg.

The Famous Burger with Added Bacon and Egg.

I can honestly say this was one of the best burgers I’ve ever eaten. Two thin beef patties were smothered with cheese and nestled between pillowy buns. The added bacon was thicker cut and had a soft but enjoyable texture. Definitely worth the hype!

The following day started at 360 Chicago for one of the best panoramic views of the city from the 94th floor. They also have a “thrill” ride called Tilt which Tommaso made me do but it wasn’t as scary as I imagined.

One of the most popular tourist attractions is the Chicago River Boat Architecture Tour where you can marvel at and learn about all the incredible buildings along the river. After all, the city is the birthplace of the skyscraper! This 90 minute river cruise was so informative and our tour guide was incredibly knowledgeable and enthusiastic.

After the river cruise we needed a little afternoon snack and headed to Portillo’s, a famous chain for American cuisine. Of course I had to try a Chicago dog! It was surprisingly tasty with mustard, relish, celery salt, freshly chopped onions, sliced red ripe tomatoes, kosher pickle, and sport peppers on a poppyseed bun.

We chilled at the hotel for a few hours before our casual dinner at Galit, a lively Middle Eastern spot with vibrant food.

The following day started off early by going to brunch. Kasama was easily one of the places I was most excited to try as they’re the first Filipino restaurant to earn a Michelin star. During the day they offer various pastries and a few brunch items whereas at night they offer a tasting menu. I wish I could have tried their dinner menu as the daytime menu was superb.

Ham and Cheese Danish.

Cinnamon Bun; Oatmeal Cream Pie with Dulce de Leche and Rhubarb Jam; Citrus Poppyseed Poundcake; Ube and Huckleberry Basque Cake; and Apple Hand Pie.

Filipino Breakfast with Fried Egg, Garlic Rice, Longanisa Sausage, and Tocino.

We loved everything about Kasama. The pastries were beautifully crafted and the Filipino breakfast bowl was an explosion of flavors. Highly recommend visiting here!

After a fantastic brunch we spent the afternoon at the Garfield Park Conservatory admiring all the stunning plants and flowers. It’s one of the largest botanical conservatories and has thousands of plant species from all around the world.

Surprised that we’re hungry again?! We had a late lunch at Manny’s Cafeteria & Delicatessen, another iconic institution which serves up classic Jewish favorites. It’s a pretty large cafeteria style restaurant and we shared the matzo ball soup and reuben sandwich with pastrami. Both very tasty!

Reuben Sandwich and Matzo Ball Soup.

We relaxed at the hotel for a few hours before our dinner at Elske, one of my favorite dinner spots during our entire trip.

The next day started off strong at Bang Bang Pie & Biscuits. This tiny shop has some killer homemade biscuits and slices of pie and everything on the menu sounded amazing. The biscuits were warm, soft, and buttery and I easily could have ordered every type of biscuit sandwich because they all looked incredible. Tommaso really wanted to try the chicken pot pie and it was quite good but the biscuits reigned supreme. Of course I had a hard time picking which slice of pie to try. Typically I would go for key lime pie as it’s one of my all time favorites but I decided to switch it up and try something different with the chai custard. The subtle coconut flavor from the crust paired nicely with the spice notes from the filling.

Biscuit with Ginger Sage Sausage, White Cheddar, and Peach Habanero Jam. Biscuit with Ham with Gouda, Herby Mayo, Pickled Red Onion, and Arugula.

Chicken Pot Pie.

Chai Custard Pie with Whipped Cream and Coconut Macaroon Crust.

After breakfast we headed to the Art Institute of Chicago, one of the largest and oldest art museums in the world and one of the most visited attractions in the city. This famous museum holds 300,00 works of art from all over the world spanning centuries. While neither Tommaso or I are art enthusiasts, we both thoroughly enjoyed the museum and admired all the types of art.

After several hours at the museum, we walked to Millennium Park which is right in the middle of the city. One of the most recognized sculptures of the city is located in the park known as Cloud Gate aka The Bean. This 110-ton sculpture is made from a series of polished stainless steel plates and reflects the city’s famous skyline and the surrounding greenery.

Last stop of the day was to another observation deck for an awesome view of the city. Skydeck Chicago, located inside the Willis Tower, is higher than 360 Chicago which we visited a few days ago. Located on the 103rd floor, they also offer The Ledge, a glass balcony which extends outside the tower.

After a jam-packed day we had a casual dinner at Virtue for some satisfying soul food.

Our time in Chicago was sadly coming to an end. Our last day started off with lunch at Birrieria Zaragoza, a tiny restaurant specializing in traditional birria (stewed goat meat). Everything was delicious and while the restaurant was a bit out of the way, it was totally worth the trek.

Birria Tacos.

Cabeza Taco.

Quesabirria Dorada.


The afternoon was spent at the Museum of Science+Industry, a very cool interactive museum with all sorts of exhibits. The highlight was exploring the German submarine U-505 that was captured during World World II. The museum closes at 4PM so we didn’t get to explore as much as we would have liked.