Hola Chicago.

72 hours in Chicago. 

A perfect weekend in my book is a weekend getaway with my boo. We agreed we needed more time away exploring other cities in the US, so we kicked off Gavin’s birthday doing just that. A weekend in Chicago is the perfect amount of time to see just about everything, you can probably do it all in a day or two. Chicago reminded me a lot of San Francisco, or at least what San Francisco used to look like. Chicago’s streets were clean and not once did we feel unsafe walking around, night or day. Getting around the city was easy enough by foot or uber. Something Gavin and I couldn’t get over was the amount of honking the cars do. There were times cars would honk at what seemed like nothing. We were in an uber and the driver started honking at the red light, it was hilarious. Overall the trip was great, and we enjoyed everything Chicago had to offer during our stay!


We were both excited about Chicago mainly for the history throughout the city and sitting in cafes where notorious mobsters once sat. We really wanted to do a mobster walking tour but ultimately decided it’s not something we should really support. Looking into the tours I started to think, why are european-american gangsters glamorized and portrayed as “the cool bad guy” and black/brown gangsters are seen as demons and portrayed as the most dangerous people in the world? The history of the city is always interesting to learn but we decided to do other things that Chicago had to offer…

Chicago Theatre: Where you’ll find the popular Chicago sign. We passed by the theater a few times and each time there never seemed to be too many people taking photos. The sign is so big that you can stand from across the street and get great photos. The theater looks beautiful at night when all lit up, be sure to stop by and admire the lights.

River Walk: When the streets and traffic get to be too much, taking a flight of stairs down a level to the river, makes for a great escape. The view of the skyscrapers along the water is beautiful, you can sit at a cafe found along the river walk and take in the view. You can also watch all the boats float along the river. It was great, even though it was extremely cold, I can only imagine how beautiful it is during the warmer months.

Starbucks Reserve: We were lucky enough to be in town during the grand opening of the Starbucks Reserve. These Starbucks are not like our everyday locations. The Reserve locations have a one of a kind menu and food options. The line was ridiculous, so we just admired it from afar and moved on. But you get the chance to visit Chicago, be sure to check it out, especially if you’ve never been to a Starbucks Reserve before. 

Cloud Gate: So there’s two kinds of people in the world, ones that don’t want to be bothered when taking photos, and ones that like to bother. When it comes to a touristy place, it’s hard to get a good photo without others walking into your frame, or interrupt your focus by asking for a photo. So I try to time the perfect time when to go, so that I can get the shots and go. Cloud gate is one of the busiest touristy places. My only request during this trip was for us to wake up early enough before it became too busy. We arrived at the gate around 7am on a Monday morning and it was perfect. The sun was rising, creating a pick and yellow light in the sky and there were a couple of other people there too with the same idea. The Cloud Gate, looks like a bean and reflects the city. The bean is massive, and photos really do not do it justice. 

Ferris Wheel at Navy Pier: The ferris wheel was something we added to our to-do list spontaneously because we got through our list quickly and didn’t know what else to do. To kill time we walked to Navy Pier, and it seemed like the longest walk of my life. You do get some of the prettiest views of the city, but I would recommend coming here when you’ve hit all your to-dos. 

Michigan Street: Similar to Market St. This is the main street that runs through downtown and where you can do all major shopping. The same major retail stores that are found in every downtown are found here, so if you’re not big into shopping, this probably won’t be super exciting.

The SkyDeck: I honestly have mixed feelings about this place. located at the top of the Sears Building, be prepared for long lines, a security checkpoint and longer lines. The idea of getting some epic photos made the wait not that bad, but then we realised you have 1 min to take your photo. After waiting for over an hour, we had ONE MINUTE to get our photos. There’s employees there timing and then call security if you go over the time limit. Gavin and I had to come up with a game plan to quickly get our photos in a timely manner, it was hilarious talking through it but this is definitely a visit-one-time place. 


There are so many places in Chicago to visit when it comes to food and drinks. Like San Francisco, there are so many to choose from, it can feel overwhelming. Since it was our first time visiting, I figured it would be smart to make reservations to multiple places for different times of the day. Gavin hates waiting in lines, especially when he’s hungry. The plan was to order small plates at each place so that we can visit more places and have a place to escape from the cold. Some of these small plates were filling, so we had no appetite to visit another place. So here are the places we loved and one place that was a disappointment. I’ll also add all the places I had on my list. 

Au Cheval: If you only had one place to eat at, while you were in Chicago, eat here. Shout out to my friend Linda for recommending the best burger I have ever had.  The restaurant, I believe, doesn’t take reservations. I think we waited to be seated for 45 minutes, so we went to a bar nearby to kill some time. The restaurant has a feel of an upscale diner with both counter and booth seating yet with a low lit -cozy atmosphere like a steakhouse. The waiters are buzzing all around you, the moment you walk in and you can see the cooks and bartenders working away. Everything on the menu sounds delicious but there was only one reason we came here. We came for the bacon cheeseburger topped with an egg. Nothing about this burger was ordinary. The bacon was thick sliced and carmalized, the egg was perfectly cooked and topped on a fresh beef patty with cheese, just to be all placed together in between two brioche buns. I swear, I never tasted anything so delicious, Gavin and I didn’t speak the whole time we ate. It was incredible!

Bernie’s Chicago: Our first restaurant we visited, and a special one we will always remember. We made reservations through Open Table, and noted that we were visiting for a birthday. When we arrived they had a special card waiting for Gavin, with a kind note. All the employees were so kind and Britney, our server was the best. She recommended the best options, and really made our first dining experience perfect. The restaurant is beautiful, with gold and teal blue accents. There was a beautiful bar that I’ve seen on PInterest many times. The food was also delicious. We ordered an omelette but the best was what Britney recommended, the hummus with land and fresh pita. I’m a fan of hummus and Gavin not so much, but even he loved it. Then to top it off, they surprised Gavin with their famous donuts. Donut holes with ricotta, rolled in cinnamon and sugar. It was a great way to start our trip!

Beatnik – West Town:  A one of a kind place for drinks and appetizers! I loved this place so much, for its decor and vibe. There are two Beatnik locations, one is located near the water and the other away from the city. Both locations are beautiful but the one in West Town has a beautiful indoor patio. Half of the location is a restaurant and the other half an indoor patio with two bar locations. The place was aesthetically pleasing in the sense that there was no corner undecorated, from the tiles to the ceiling, there was so much to admire. The drinks were hand crafted with a full menu to pick from, it was hard to choose. After a couple we found our favorites and stuck with them. This bar was one of a kind and definitely worth the trip!

The Berghoff Restaurant: The only disappointment on this trip was visiting here. From what the restaurant looked like online, we thought we were going to visit an authentic German restaurant, where the big mobsters once dined at. This felt like a tourist trap. The restaurant was huge, and decorated beautifully with dark wood trims and full of Christmas decorations. We immediately felt out of place because the customer base was elderly. There were probably plenty of red flags that told us to go elsewhere. Twenty minutes after ordering our food it arrived, and that’s when we knew this place was a rip off. I ordered spaetzle, which is a traditional German dish that I had twice. Once in Bolzano with my friend Stef and another time, a roommate of ours from Germany made it from scratch. I was so excited to have it once again but that excitement was gone the second I saw what was on my plate. Spaetzle reminds me of a German Mac n cheese but with a sauce similar to Alfredo sauce. What was on my plate looked like.. I hate to say it but maggots. There was no sauce just dry looking Mac noodles. Gavin’s breaded chicken tasted like it was frozen, ugh the whole experience was awful.  I think what took us by surprise was that this restaurant has 4.5 starts and over 1000 reviews. 

Firecakes: Just one of the delicious donut places to choose from. We popped in after visiting the Cloud Gate. It was early enough that we scored on fresh donuts and coffee. They had a variety of traditional donuts and unique flavors. I think there’s a few locations in the city, so make sure to stop by and grab a fresh donut.

Deep Dish Pizza: A must when in Chicago. I personally do not like too much sauce on my pizza, so I wasn’t too excited to try a deep dish. There was one place that looked incredible called Chicago Pizza and Oven Grinder. Literally a bread bowl full of cheese and some sauce, straight out of the oven. Sadly they do not open until 4pm and we saved this experience for Monday, before we left back to San Francisco. We had to find a different place and came across Lou Malnati’s Pizzeria. We got lucky because this place was great. The food takes a while to come out but we didn’t care because we knew the pizza would come out fresh. We ordered wings for an appetizer and two individual pizzas. It was a lot of food but it was a great way to end our trip and head to the airport full and happy. 


Chicago in November is extremely cold, so cold that the snow that fell two weeks prior was still preserved. The best item packed was the heat technology thermal I bought at Uniqlo. The thermal is lined with a fuzzy fabric on the inside and long enough to stay tucked into pants. This thermal worked so well, and layered easily under all my clothes.  The second best item I packed were my Dr. Martens. I don’t own snow boots because I don’t care for snow or snow sports. I didn’t want to spend my money on something that I wasn’t going to really ever use. I can wear these Dr. Martens in any weather and they have a cute platform. They were great in the icy streets prevented any kind of slipping. They were also comfortable enough to wear throughout the day without having to really break them in before hand.

Chicago for the weekend was a great mini vacation. We loved it so much we started to look at the possibilities of maybe making a move the Windy City. We were in shock to see that the prices in apartments were very reasonable. We have to do more research but for now, I am looking forward to visiting again but isn’t he warmer month to enjoy all the rooftops!

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