
This wasn’t my first Chicago trip, but it was definitely my favorite. This time, I know the details. I was staying over in Lincoln Square/Ravenswood, which was a close walk to the train, and across the street from a little park. I was pumped to have free street parking available, and often right in front of the apartment. I got there on St. Patrick’s day, and my sister met me over there so we could spend the weekend exploring Chicago together. The river was green, and we were in high spirits.
I Ate and I Ate and I Ate Some More
I don’t remember much of my previous trip beyond getting Lou Malnati’s which was a pretty great deep dish spot and very well known. If you want to go classic, this is an expected choice while you’re in Chicago.
We started with a phenomenal dinner on the river at Beatnik on the River. The menu was definitely very pricey, but we knew what we were getting into. It offered some great views on the river and very comfortable ambiance that we took advantage of for hours and hours… while I nursed my drink. Downstairs, there is seating right along the water too.

We made it out of the apartment by 1pm that day and headed to the first bar, Kirkwood Bar & Grill, where we grabbed lunch and drinks. The food was stellar, and my expresso martini certainly hit the spot. Next, we headed to a different neck of the woods, which was a short drive away into Old Town to go to Declan’s Irish Pub where the drinks were very reasonably priced. The Rabbit Hole was the next bar we stopped into, and the vibes there were really cool, but far too crowded to get some seats. Check it out for some games that you can play, like Jenga and Connect 4.

By now, it was dinner time, so I picked out the Broken English Taco Pub for dinner. We ended up splitting some ~incredible~ nachos (and reasonably priced), and split an order of two tacos, along with some drinks. Broken English Taco Pub had a really cool aesthetic, with neon lights and just very colorful vibes, so I was happy that we were able to make it.We ended the night at Levain Bakery, which has some famous cookies that weigh like 5 lbs. It took me a good 3 days to eat mine.
The next day, we were much faster about getting moving early to take advantage of the day, since my sister had to get to the airport by dinnertime. We started out by heading over to Fulton Market Kitchen (a food hall) for breakfast, and JEEZ LOUISE was this place good.
Inside the hall was a place called Beatrix (similar to the name of the first place)and I was just blown away by how good breakfast was. Definitely a bit pricey, especially the drinks, but the food was so worth it. I highly recommend the egg sandwich, which has some brown sugar bacon that took my breathe away. The omelet totally smacked too. They have a ton of drink options too since they’re a bar and a coffee/bakery shop. They are also all around Chicago, so you can find one in most areas.


Next up was Restoration Hardware, The Gallery at the Three Arts Club, which is a furniture store that doubles as a very elegant, and delicious dining spot. Make sure to book reservations in advance, because we ate at 4pm since it was so busy. Now, the food here is something I would always write home about. I highly recommend taking a walk through the building while you’re at it, for décor inspiration, and to check out the roof deck which offers more city views (pictured).
I got the gem lettuce salad with chicken, to die for. We also split some incredible truffle fries, I got a Peach Bellini which never fails to disappoint. That being said, definitely the most expensive spot. That side of fries was $20… but honestly kind of worth it. The ambiance is unparalleled, with views of the sky and glamorous fountains and greenery inside the restaurant.

The next night I picked up a deep dish pizza from Pequod’s, which is a popular spot that is definitely out of the way from the main strip. It was a really good pizza, and mildly priced in my opinion. I spent the small remainder of my night back in the apartment I was housesitting. My last meal was lunch early the next morning at Jerry’s, which had some good coffee, and a very delicious sandwich.
Some Fun Things to Do in the City
I need to mention parking first and foremost because it adds up really quick in this city. The annoyance of driving is how many parking meters we had to pay for from place to place. The pricing varied from $4 an hour to $9 an hour.







