When my boyfriend found out he was going to be flown to Chicago for a work trip, we both got so excited! Luckily I had saved enough travel points with my Chase Sapphire card to cover my airfare, and since Chicago was a city we both had always wanted to visit, we were so thrilled at the chance to go - even if it was a short trip!
We would be staying in the River North neighborhood, so I of course immediately started researching all of the different food & drink places within walking distance to check out. Keep reading to find out where we went for a 32oz meal-topped Bloody Mary, fun & unique tiki cocktails, and of course...Chicago-style deep dish stuffed pizza!
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Click here to see my quick video tour of our trip!
Asian-fusion brunch spot with the 32oz Sumo Bloody Mary
Once I saw the Sumo Bloody Mary online, I knew I had to have it! Sunda has a great brunch menu filled with creative takes on some of my favorite Asian food - there's a little bit of Korean, Japanese, even Filipino cuisines, as well as a sushi bar! If it wasn't for this Bloody Mary, I would've had a really hard time choosing between entrees, everything sounded delicious. However, since this behemoth of a cocktail came with so much food, we decided to start with this and a Philly Roll and honestly, that ended up being the perfect amount of food for us that day for brunch.
The Sumo Bloody Mary comes with: 3 pieces of lumpia egg rolls, karaage (Japanese fried chicken), baked snow crab hand roll, pork belly bao bun, longanisa (Filipino sausage), grilled cheese with Tocino (Filipino pork belly), a fried potato and several slices of cucumber.
Considering that you get all of this food on top of a 32oz cocktail, $38 is totally worth it. If you're a fan of wasabi or horseradish in your Bloody Mary's, then you'll love this one. I prefer more of a hot sauce flavor, but it was still pretty good. I sadly wasn't able to finish the entire cocktail, but I got close! My boyfriend got their old fashioned, which was also tasty!
**I believe the Sumo Bloody Mary is only available during brunch hours, which are Saturdays & Sundays from 11am-2pm.
Address: 110 W Illinois St, Chicago, IL 60654
One of the best Stuffed Deep-Dish Pizza spots in Chicago
When in Chicago, amirite? Chicago-style deep dish pizza was of course on our list of things we wanted to try during our quick visit, and luckily there was a Giordano's right around the corner from us! Giordano's first opened in Chicago in 1974, and now have locations all over Illinois as well as a few other states. They're known for having some of the best stuffed deep-dish pizza in Chicago, so we were excited to check this place out!
The pies are pricier than we're used to (Small: $28.95, Medium: $35.85, Large: $43.15 for the deep dish pizza we wanted), and though we were sure these pies were probably big, we weren't sure if a small pizza would be enough for the both of us, so we decided to order a small "Meat and More Meat - Deep Dish" (pepperoni, salami, sausage & bacon) and small "Bacon BBQ Chicken - Thin Crust" (bbq chicken, bacon, & balsamic onions).
We were able to conveniently order through their website and walk down to pick it up. There was a separate counter for to-go orders, which was nice because the waiting area around the host was crowded and busy - we took that as a good sign that the pizza was worth it!
The first thing we realized when we got the pizza? Though the boxes looked small...they were heavy. When we opened them, we quickly realized that the deep dish was not so much a pizza as it was a thick, pizza-style casserole. The thing was huge! We definitely didn't need to order a second pizza, however, both pizzas tasted amazing! The thin crust felt closer to a regular pizza, so if you like your thin crust really thin and crispy, they do have an "extra-thin crust" option.
**There are locations all around the city, but this is the location we went to.
Address: 730 N Rush St, Chicago, Illinois 60611
Largest Starbucks Location in the World, One of Six World-Wide Starbucks Roasteries
I know what you're probably thinking: "It's your first time in Chicago...and you went to a Starbucks?" Totally get it. However, if you've ever been to a Reserve Roastery location, then you already know that these locations are no ordinary Starbucks!
Not only are there just six Reserve Roasteries in the world, the Chicago location happens to be the biggest! This 5-story Starbucks Reserve Roastery has an experiential coffee bar, barrel-aged coffee bar, craft cocktail bar, Italian bakery, rooftop terrace, and gift shop. I love that their website describes it as "five stories of coffee theater."
Each floor offers something different, and throughout the building you can order:
something savory (like chicken cacciatore, pizza, lasagne bolognese)
something sweet (like tiramisu, raspberry cheesecake, cinnamon roll)
breakfast (like sandwiches, avocado toast, frittata)
alcoholic beverages (like an espresso martini flight, roastery old fashioned, wine & beer)
non-alcoholic beverages (like smoked cold fashioned, strawberry balsamic spritz, mulled spiced coffee)
and of course, a large variety of coffee & tea
To see everything on the Roastery menus, check out this page and scroll down to "Illinois."
You can book a tour of the Roastery if you're interested in a more immersive, in-depth experience of the coffee roasting process, or you can wander in like we did and explore each floor on your own. Seating is like a coffee shop, where it's first-come, first-serve. You still go up and order at the counter or bar, and then take your food & drinks to your seat. Each floor seems to offer a specific thing, so you might have to order on several floors (I ordered a latte on one floor, and my boyfriend saved our table while I went downstairs and bought a sandwich).
I honestly could spend all day checking out their menus, and wish we had more time! If I had the chance to come back, I'd definitely get the espresso martini flight. For this visit, I ordered the Hazelnut Bianco Latte (Starbucks Reserve espresso with steamed, house-made hazelnut praline-infused milk), the Prosciutto & Parmigiano-Reggiano on Brioche sandwich, and a chocolate-chip cookie for later. Everything was delicious!
Address: 646 N Michigan Ave, Chicago, IL 60611
Speakeasy Tiki Bar with Tropical Cocktails & Bites
This tiki bar was recommended to us by a family friend, and was SO FUN. It's located in an alleyway between Hubbard & Illinois (if you're walking down Hubbard toward Clark St, you'll see the alleyway on your right. If you walk past Firecakes Donuts on your right, you've gone too far). There are flaming tiki torches out front, and after stepping into a doorway, you head down steps into a dark, tropical-themed tiki bar. The attention to detail with all of the decor was amazing!
To add to the fun, the presentation of the cocktails was incredible! They use heavy-duty ceramic tiki mugs for the cocktails instead of regular glasses, and they have several different style mugs for the variety of cocktails. The extensive list of unique cocktails on their menu made it difficult to choose just one, however, we were finally able to make a decision and were not only impressed but very happy with our selection.
I went with the Isle of Mango (vanilla-infused blended scotch whiskey, mango, pineapple, horchata orgeat) and my boyfriend got the Lower Wacker (bonded bourbon, 151 guyana rum, maraschino, red vermouth, honey, lime, grapefruit). To check out their cocktail menu, click here! Side note: any cocktail with a skull image after the description is a warning that the cocktail is strong.
They do offer some Polynesian-inspired food items - to check out that menu, click here! I wish we were able to stay and try some food, but we stuck to the two cocktails since we were heading to dinner afterwards across the street! Which leads us to our final Chicago food location!
**It's open seating at the bar, but you need a reservation for their tables.
Address: 435 N Clark St (in the alley), Chicago, IL 60654
Casual-chic Italian-American Restaurant with Fun Vibes and Great Ambiance
For a celebratory last dinner in Chicago, we both were craving Italian, and were so happy we went to Il Porcellino. There was a long list of Italian restaurants in the area, so trying to pick one was a challenge. However, Il Porcellino was not only highly-rated, it was within walking distance from our hotel, and across the street from Three Dots and a Dash, so it seemed like a no-brainer!
I immediately fell in love with the decor and ambiance when we walked in (just check out this pic on their site! So gorgeous!) It was dimly-lit with candles on each table and beautiful hanging lights throughout the restaurant. There were framed photos and vintage decor styled on shelves around the exposed-brick walls. It felt romantic and fun, without the stuffiness of a white-linen upscale restaurant.
Based on the reviews, we knew to make a reservation, and made one on OpenTable. By the time we got there, the place was packed, so we were happy we made one!
Our server was amazing, our drinks were amazing, and we loved our food! We started off splitting a small caesar salad and calamari, and then we shared the chicken parmesan with spaghetti, their famous lasagna, and garlic bread. The garlic bread was tougher than we were expecting, it was more like boule bread as opposed to a softer garlic toast (they did have a cheese toast that looked more like what we're used to, if I get the chance to come back I'll try that!). If you come and can only get one thing, definitely get the lasagna!
It does get a little loud in there, with the music and the conversations, but that didn't bother us at all - we loved it!
The only qualm we had with this place was the person at the greet stand ignored us for a good while. There were three men in suits ahead of us, and he chatted with them until they were brought to a table. Meanwhile, a line was starting to grow behind us, and there was no greeting or checking us in so we could get out of the entryway. A couple people behind us in line actually turned around and left. It was very odd and pretty rude, but who knows, maybe the men were VIPs. Once they were sat, another gentleman came up, and he was pretty friendly and got everyone checked in. After that, we had an awesome experience!
I would come to this place again and again for the food and ambiance. To check out their menu, click here!
Address: 59 W Hubbard St. Chicago, IL 60654
Honorable Mentions
With only a couple short days in Chicago, there were still of course many different places we wanted to check out, but weren't able to. However, if you're finding yourself with extra time in downtown Chicago and wanting some cool places to check out, here are some of the places that were on my list:
For cocktails: The Aviary
(I don't think I've ever seen cooler looking cocktails!)
For a variety of food & cocktails: Time Out Market Chicago
For breakfast: Beatrix - River North
For brunch: London House and Wake 'n Bacon
For grass-fed burgers: DMK Burger Bar and Butcher and The Burger
**Not all of these options are in the River North area.