The Deep Dish on Chicago
We had a very warm welcome to the Windy City of Chicago. While the city was hit by an unusual heat wave, we were prepared for a sunny weekend full of fabulous food, subway surfing, river walking, and lively night life.
Also called “Chi,” Chicago is known for its manufacturing and finance industry, savory deep dish pizza, love for baseball, and gorgeous lake. While I left still wanting more, 3 days was just enough to get a feel for the city. I’ll walk you through some helpful tips I wish I knew before going and our favorite things to do and places to eat. It’s a city as rich in history as it is rich in food, so bring your appetite.
3 Cheese Bread at Lou Malnati’s
Day One: Discovering Downtown & Deep Dish Pizza
Despite the River North being conveniently located by the river and all things touristy, one recommendation I’d give is to stay just outside of River North. Though it’s a bustling vibrant neighborhood, being affluent means prices for even lower tier hotels are incredibly expensive. Staying in Lincoln Park, West Loop, or Fulton Market District will give you better bang for your buck, and it’ll only take you 10-15 minutes on the subway transit to get from place to place.
One of the first things to try in Chicago is their pizza. Although your heart may lie with New York or Sicilian pizza styles, this is a hallmark of the Chicago experience. We ate at Lou Malnati’s in River North as recommended by friends. Shockingly, the wait to eat inside was 3 hours even at 5 pm, but we were able to get a seat right away outside. We ordered the caesar salad, 3 cheese bread, and Original Style Pizza. Let’s break down the OG pizza by Mr. Malnati - starting from top to bottom. The Original has a chunky tomato sauce layered on top of an Italian sausage blend (it looks like a sausage pancake) which rests on a thick layer of mozzarella cheese, all lying on a bed of flaky, cornmeal-like crust.
The Original
If the wait for Lou’s Malnati’s is too long, rest assured that Pequod’s and Giordano’s are excellent alternatives! Our local friends actually say Pequod’s Pizza is superior to Lou Malnati’s, but we couldn’t stay to tell the tale on our own. It does have an impressive 15k reviews, but you’ll have to let me know the dish if you try both.
Brennan had shipped frozen pizzas straight from Lou Malnati’s for my birthday last year so that was technically my first Chicago style pizza! If you love it, you won’t have to travel all the way back to Chicago for a taste of cheesy goodness.
Chicago has a blend of historical food influences including Jewish, Greek, and Italian flavors. For this trip, I tried to put my favorites - sushi, tacos, and poke - on hold since they’re so accessible in California.
As day turned to night, we met up with a group of friends in Lincoln Park which took us all but 10 minutes on the train from downtown. After much debate, we decided to hit Kingston Mines, a vibrant blues club with two rooms, each equipped with their own performance stages. Throughout the night, bands switched off performing in either room. We ordered outstanding hot wings (some of the best I’d ever had), fried okra, and fried shrimp, as we enjoyed the tunes blasting from the stage.
Some other bar recommendations are Arbello for more classy cocktail vibes, Old Crowe for post-Cubs game food and drinks, Three Dots & a Dash for a shmoozey tiki cocktail and speakeasy experience, or the Tin Lizzie for competitive turtle racing.
Day Two: Architects of the Millenium
Our second day was much more planned out. Kicking off our morning on a late note, we rushed from our hotel to the Chicago River Boat Architectural Tour. Dashing through locals and tourists alike, we stopped for a quick coffee at Cafe Umbria, then headed for the tour meeting point.
As we lined up by the river, we could see our boat which easily sat 50 people. The best part of the tour was getting to cover so much ground in only 90 minutes. We learned about the architects who created the beautiful post-modern, brutalist, and modernist skyscrapers and how the city re-routed it’s once toxic river elsewhere to make theirs swimmable (rip St. Louis). The river was dotted with tour boats as well as small kayaks and party boats. Many locals dressed in swim suits take boats out to swim in the lake. If you’re up for it, you should definitely rent a party boat or kayak in the river.
After our tour, we walked down Magnificent Mile which is a shopping hub for big brands like Nordstrom and Ralph Lauren. We did a bit of high end shopping and passed the Chicago Tribune building which interestingly has pieces of other landmarks in it’s walls. Pieces of the Berlin Wall, China Wall, The Great Pyramids, and other landmarks are embedded into this building. This was a deliberate design and “symbol of the newspaper's global reach and historical significance.”
Chicago Tribune Building
Along Magnificent Mile we stopped by Stan’s Donuts, a popular donut shop that didn’t fall short of its high 2.1k ratings. The lattes were delicious and the toffee donut was decadent and yummy. Next door to Stan’s Donuts is also the Nutella Cafe. We aren’t all that crazy about Nutella, but it had a long line that would turn heads. It’s a very popular spot if you’re looking for a sweet brunch option!
Our last stop before dinner was Millennium Park. I had to see the Cloud Gate, aka “The Bean.” The Bean is located in Millennium Park. We approached the looming sculpture, walked under it’s metallic underpass despite the chaotic crowds. It’s right next to the Art Institute if you decided to pair both together in your visit.
Afterward, we took a nice break and bought a cup of watermelon and mango from a fruit stand. We plopped on the beautifully kept lawn of the park. The walkable city with its green spaces, easy transit, and love for baseball made me reminisce San Francisco.
We had an hour before dinner with friends so we headed to our hotel to get washed up from the heat beating down our necks. Our dinner plans were at Havana, an undeniably delicious Cuban restaurant. You’ll want to book a reservation for any restaurant in downtown since it’s so busy. There aren’t a ton of places that take reservations for over 8 people, but Havana was a great find. We shared a pitcher of margaritas - mango, passionfruit, guava and original. The menu did not disappoint with it’s ensalada con camarones, cubano sandiwches, roasted pork, or cocktails! 10/10 from me.
Ropa Vieja
After dinner, we went to Fulton Market District, another great stop for tourists. It’s a busy street with both casual and fine dining, fun bars, and a multi-level food market. The Time Out Market has various eateries, making it a great place to try multiple Chicago bites in one stop. Time Out also has a rooftop bar/club with dancing and city views, however, a lot of people rent this space out for events or occasions.
While we didn’t make it on the birthday list, we went to the 2nd floor bar to enjoy cocktails and a comfy AC’d social space. Colorful lights, high tops, and couches lined the floor, making it a perfect spot for a big group.
Time Out Market
Afterward, we ended the night at SUNNYGUN. I loved this bar for its outdoor casual cabana vibes as well as indoor cocktail bar atmosphere. It was a bit nicer than our divier Kingston Mines, offering decorative strung lights, woven sofas, and desert decor. This would definitely be a favorite of mine if I lived here.
Around the corner, there’s also a bar called MONEYGUN - a sister bar of sorts. Anyway, our friends say it’s another good option if SUNNYGUN is at full capacity.
Day Three: Fine Art & Even Finer Dining
Despite a hangover Sunday morning, we - or should I say, I (Brennan decided to sleep in and let me have a solo adventure) - decided to make a dash for Kasama.
Kasama is a top tier cafe by day and Michelin Star restaurant by night in Ukrainian Village. Boasted about by our local friends, Kasama is a Filipino hot spot that create extremely long lines every day. It was also mentioned in an episode of “The Bear” on Hulu. I got there before 8 am and was still 18th in line.
I waited for it to open at 9 am when I learned the line was only for dining in. Since I was just grabbing pastries to go, I could’ve ordered online and just showed up to pick up my baked goods. Unless you want to sit down and eat a full breakfast, do a mobile order for pick up and get your coffee and pastries ASAP.
Regardless, I was curious to see inside and peep over customer shoulders to see their dine in menu. While the cafe offers a divine selections of tarts and croissants, the dine in options had savory bites like Chicken Adobo, Lumpia Shanghai, and their famous Breakfast Sandwich. My mouth watered as I waited to pay for my Black Sesame Latte. I ordered more baked goods than we’d end up eating, but I couldn’t help myself.
We shared a Cardamom Bun, Chocolate Tart, Black Sesame Coconut Macaroon and Matcha E’Clair. The Cardamon Bun was crispy and sticky and the macaroon was chewy and decadent. I regretted not getting the Apple Tart and Ube and Huckleberry Basque Cake, but I knew I’d be back. If you do decide to come for breakfast at Kasama, get there 1-1.5 hours early. It’s worth the wait. And if you decide to enjoy their multi-course Michelin dinner, be sure to book a reservation 1-2 weeks in advance.
I ubered home to share my treats with Brennan. We had lunch plans in a bit so we refrained from inhaling the sugary breakfast. After resting and caffeinating, we got ready for lunch at The Smith. The Smith is a favorable brunch spot in River North. Brennan and I met with one of my childhood friends who I hadn’t seen in nearly 10 years. Our double date brunch spread consisted of Shrimp & Grits, Salmon on a Potato Waffle, Avocado Toast, and Omelettes as well as free cocktails with our orders! I’d say it’s very comparable to restaurants like Breakfast Republic.
While I did enjoy The Smith, it’s got the atmosphere of a larger American brunch chain. Most spots downtown are larger chains so if you want to explore more mom & pop shops or farm to table restaurants, you’ll need to look to cozier, neighboring areas. Tweet Let’s Eat, Little Goat Diner, Cafe Con Leche, and TARY are some recommendations we got as well. Or if you want a brunch spot with a view, there are also plenty of rooftop spots like The Hampton Social in River North.
After eating, we all went to The Art Institute of Chicago, which is an expansive art museum that would take more than one visit to cover. The tickets are $32 per person with a discount for residents! Get tickets in advance to skip the line - no time entry required.
Roman Exhibit in The Art Institute of Chicago
We enjoyed art from East Asia, Ancient Rome, and Ancient Egypt. By the time we strolled through gallery after gallery, Brennan and I hit a wall. With the heat, hangover, and walking catching up to us, we were ready to take a break in the park. The four of us strolled by Grant Park and checked out the lakeside view. Bikers and runners dotted the lake front. We were thankful for any breeze that could cool us off. We laid in the shaded grass for a bit, giving our achey feet some relief, and chatted with our friends. The parks here are well kept and a great spot to hang out or picnic with friends!
Once our friends headed home, I had to face the tragedy of Mr. Beef’s hours. Our dinner plans that night were supposed to be to dine at the famous sandwich shop that our favorite show, “The Bear,” is based on, but I found out too late that Mr. Beef is closed on Sundays. It wouldn’t have been such a big deal if not for our flights departure at 9 am Monday. I was bummed to say the least. It was admittedly my #1 “must do” for our trip, and I hadn’t had the foresight to check the hours.
Lesson learned, lesson shared. Go any day except Sunday.
Anyway, I requested we still go see the shop, so Brennan and I trekked along to Mr. Beef for a peek at the “set.” Just another totally necessary request by me.
If you are craving a sandwich, Mr. Beef is the way to go. My best friend Ashlynn that we’d seen said it was impeccable. She had “The Italian Beef,” their signature sandy with thinly sliced roast beef on a sturdy roll, typically dipped in au jus and topped with sweet or hot peppers. While the staff is intimidating tough looking dudes, they’re very nice, she says. Oh and it’s cash only. Be sure to stop by if you love The Bear or are hungry for an Italian beef sandwich, Italian sausage, or Chicago-style hot dog.
Since we didn’t have plans for dinner, I pondered how I could fulfill the hole that was my beef-less stomach. I knew that Chicago was a home to top chefs and fine dining enthusiasts, so I scoured through restaurant options that were last night worthy. My list of possibilities included a few Michelins like Ever (also in The Bear), Smyth (Brennan’s favorite), and Oriole, as well as some other highly reviewed restaurants like MCCB or QXY Dumplings in Chinatown, La Luna, Robert’s Pizza (on the river), and RPM Seafood (my friend is a cook here!). However, as you can imagine, reservations were scarce so last minute.
After getting hit with the “full booked” notification, I was surprisingly able to get a last minute resy at Next Restaurant, a Michelin Star in Fulton District Square. They were currently doing a collaboration with the Italian Chef, Massimo Bottura, who was Top 100 Most Influential People in Time Magazine in 2019. He founded the 3 star Michelin, Osteria Francescana, in his hometown Modena, Italy - sure to be on my dine before I die list. We were very excited for our 9 course meal that blended influences from both Italy and Chicago.
We were originally going to eat the 5 course (outdoor mandatory) which costs $135 per person, but the heat and noise were so unbearable outside that we were lucky to get moved inside on one condition: you have to have the 9 course meal. This is actually their requirement but who’s complaining? The 9 course is $335 per person and includes insanely creative dishes. It was plated “to the nines.”
Here were the dishes in order:
Camouflage: Here in the Woods: A bread starter with a Truffle, Hazelnut and Marsala Gelee
Three Bites to the Windy City: Chicago Style Oyster, Fish and Chips, and a “Cappuccino” (not coffee, but filled with a ceviche dish)
Green Goddess Unveiled: White Asparagus, Snow Pea, and Egg Yolk Bottarga (chef’s take on caesar salad)
Sablefish en Papiliote: Lambic Beer, Mussels, Burnt Citrus
Tortelloni Drowning in Broth: Prosciutto, Black Cherry, Warm Spices (tasted like of miso broth, mole sauce, and Christmas)
Psychedelic Abstraction of Beef, Not Flame Grilled: Salsa Verde, Bliss Elixir, Wild Mushroom and Ramp Ragu
Five Ages of Wisconsin Cheddar: 2, 3, 5, 6, and 7 Year Aged Cheese
Oops! I Dropped the Lemon Tart: Lemongrass Gelato, Limoncello, and Spiced Tart
Dolcetti: The Beatles and Elvis inspired Popsicle, with a Strawberry Shell & Banana Chips
Needless to say, the meal was a work of art. The proportions were divided perfectly so you were filled but not overly stuffed. It was a phenomenal meal and lovely way to complete our Chicago experience.
The contrast to our airport food the next morning “showcased the duality of man,” Brennan says.
Conclusion
My big takeaways from our time in the windy city are to stay close to but outside of River North, enjoy the art and architecture tours, get a Venture transit card to easily use the city’s subway, ride in a kayak or take a boat to enjoy the lake, enjoy the green parks, and absolutely positively enjoy the unique food Chicago has to offer. If I could have more time in this lovely city, I’d see a Cubs game at Wrigleyfield, go to Mr. Beef, take a boat our to Lake Michigan, and try the city’s infamous “Malört,” a Chicago-based herbal liqueur that’s become a local icon and a rite of passage for many drinkers despite it’s reportedly disgusting taste.
I genuinely loved Chicago so much and could see myself living there (but perhaps I should experience the winter weather first). If you love San Francisco, or love metropolitan cities that are easy to get around and offer nature and diverse food, you’re sure to love it too.
Sincerely,
Hannah
P.S. For those in LA, the Mr. Beef pop up is coming to California on July 12-13. I will be getting my Mr. Beef experience after all.
