Chicago: Where To Eat

In case you somehow missed my excessive instagramming (is that a word?), I spent last week in Chicago! Looks like I left you in good hands with Kelly…cupcake week?! I’m a little sad I missed out!

In these two travel posts you will get to meet my lovely sister Cassie. Since our parents are going fishing in Alaska and kinda-sorta-didn’t-really invite us, we decided to do our own trip! Neither one of us had been to Chicago, so decided it was a good place to start. (p.s. check out her fashion page @StyleByCassie #ShamelessPlug).

Since this is a food blog and all, let’s start with what we ate! Later on I’ll give recommendations of what to do. Everyone told us 2 things we had to eat in Chicago: deep dish pizza and hotdogs. So that’s what we started with (unless you count the pasta we ordered in to the hotel and devoured at 1am the first night after we landed, but we won’t get into that…)

Wrigley Field (Chicago Dog)
Our first adventure was a Cubs game at Wrigley Field! What’s more American than a hotdog, beer and baseball?? Nothing. We went out to the patio to enjoy the warm Chicago sunshine and try a famous Chicago dog. First difference I noticed already is the buns. Not just a plain, white hot dog bun, but a poppy-seed bun! Next the dogs come with grilled onions. At the condiment bar you could also add tomatoes, sweet relish or dill pickles.*SPOILER ALERT* I didn’t eat a true Chicago dog. First off…I don’t like pickles. But more importantly, I despise mustard, which is apparently part of what makes the meal a true Chicago dog. I also used ketchup (gasp!) which I have since learned is practically forbidden. Some places don’t even offer ketchup. Oops. Sorry Chicago. Needless to say it was still a delicious ball park dog, whether or not it was traditional. My beverage of choice for the day was a Goose Island beer, the 312. I’d never heard of them before but it was perfect for a day in the sun. Cassie stuck with a Mang-o-rita and said it was fruity and delicious as well.

Giordano’s (Deep Dish Pizza)
I received a lot of deep dish pizza recommendations, but we decided on Giordano’s. (Mostly because we happened to pass by it and we were both starving at the time). Just an FYI that no one mentioned to us…deep dish pizzas take forever to bake! Ok, not forever. But 55 minutes feels like forever when you’re hungry. Our waiter made sure we knew this, so we got salads to hold us over until then. The pizza was worth the wait though! We got a pepperoni, sausage and black olive pizza. Sooo good! I think the crust was the best part. It was so flavorful and chewy. Boy was it filling though. Between the two of us that small pizza lasted 2 dinners! Thankfully our hotel had a fridge so we could keep the leftovers. Proof this pizza is delicious: a stranger on the street wanted our leftovers. Seriously. I know we’re kind of small town girls, and we were a bit overwhelmed by the amount of homeless people we saw, but this guy looked “normal”. He walked right on up to us, asked how the place was, then proceeded to ask if he could have a piece of our leftovers. Sorry bud, I don’t share pizza with anyone!

Breakfast
Oak Tree
As if the food wasn’t good enough, you get 6th floor views of Michigan Avenue! It was just around the corner of our hotel and was perfect for eating and people watching down below. As soon as we walked in the door we saw the mountains of fresh homemade bread and I made a comment that I just wanted to order an entire loaf of cinnamon raisin bread for myself, so naturally I had to get the cinnamon raisin french toast! It had a vanilla bean sauce and it was scrumptious. Cassie got the banana pecan pancakes and they actually had bananas baked into the pancakes! Not just sitting on top. I need to try that myself! Definitely recommend this spot. All of the breads looked amazing and thinking back now I wish I had bought a loaf just to munch on in the hotel. Cause that’s a totally normal thing that I would do.

L’Appetito
The rest of our breakfasts were spent here at L’Appetito, this cute little Italian bakery/coffee shop/wine bar below the John Hancock Building. The walls were covered in beautiful murals of Italy, it was the cutest place! The first morning was apparently croissant day, because Cassie got the chocolate and I lucked out with one of the last breakfast ones: stuffed with sausage and egg and cheese. The croissants were so buttery and perfect. The next morning we went the pastry route and I had a cream cheese Danish (delish, again) and Cassie had a strawberry cheesecake muffin. She says it’s the best muffin she’s ever had, so I think this needs to be recreated in the future. The place was packed every morning but it was so worth it. They had a display case full of Italian desserts and a corner with wine…my skinny jeans are happy we didn’t make it back for those!

Lunch/Dinner
Castaways
We quickly realized we had planned our trip to Chicago at the perfect time. There are so many little beachside cafés and a lot are only open in the summer. After being turned away from the first place we stopped (they didn’t open until the next day) we were so excited to see Castaways in the distance on North Avenue Beach. We’d worked up an appetite riding bikes! The restaurant is right on the beach and is shaped like a boat…adorable. We ate upstairs with a view of people playing sand volleyball in one direction and the downtown skyline in the other. I’d been craving Mexican food so these nachos hit the spot. Cassie got chicken tenders and you can bet I stole some of her fries! It looked like they had a really fun drink menu, but sadly the bike rental place had our IDs and we could both pass for 16, so no drinks for us. Wah wahhh.

O’brien’s Riverwalk Cafe
O’brien’s was another cute little cafe, this time right on the Chicago River. This is another seasonal outdoor joint, however there is a full restaurant in Old Town Chicago.  We ate here the day we were belatedly celebrating Cassie’s birthday (and we had a lot of shopping to do) so I suggested we start the drinking early! Then when the Vodka Lemonades were 2 for 1…we just knew it was meant to be. Cherry Lemonade with Raspberry Vodka, on the river, in 70 degree weather? Yes please! We knew we’d be having a filling dinner so we stuck with appetizers for lunch: a strawberry spinach salad (with a side of fries, obvi) for me and some spicy chicken wings for Cassie. We were a little surprised when the food came out on paper plates, but hey…I hate dishes too! I couldn’t really blame them. This spot was so cute and I couldn’t figure out how to capture it in one picture. You had the river and sunshine and skyscrapers…it was the perfect location.

RPM Italian
Cassie’s 23rd birthday was the weekend before we were in Chicago, so I told her we’d do a fancy dinner and get dressed up. When I asked where she wanted to go, she told me “RPM Italian! Giuliana and Bill’s restaurant!”. Well I sorta knew who Giuliana was, I didn’t know Bill, but apparently they’re kind of a big deal. Even Kelly emailed me saying we should check this place out. It did not disappoint! The whole ambiance was fun. While it’s an upscale Italian restaurant, we were eating listening to music from Calvin Harris and Avicii. Yep…I can handle this. First piece of advice: make a reservation. We went on Friday night and it was packed! We lucked out though, RPM has a few tall seats at the restaurant bar (not the bar where you just get drinks and apps…like the bar where they make all the drinks just for the restaurant customers. If that makes sense…) and these seats are first come first serve. Our waitress was amazing and I felt like we had better service since we were sitting right next to her. We started out with the truffled garlic bread and Cassie got a birthday Bellini. I needed some red wine though (because we’re eating Italian! And because it’s me). I told our waitress I liked a good Malbec so she suggested I try the Bardolino, which is a lighter red. It was perfect! I need to try to find it here at home. For the main course Cassie got  Mama DePandi’s bucatini (Giuliana’s mom’s classic recipe) and I went with the handmade cavatelli. Guys…it was amazing. You can tell when pasta is homemade, it really makes all the difference. Plus the giant chunk of fresh ricotta on top was a nice surprise.

Drinks/Dessert
Martini Bar @ The Knickerbocker Hotel
Apparently sister and I had some major sweet tooths this week, because we found ourselves craving dessert each night. When we found out our hotel, The Knickerbocker, served dessert at the bar we practically ran downstairs to get some! We both got the chocolate chip cheesecake and it hit the spot. I was tempted for a split second to try to save some for leftovers, but that thought quickly passed. The bar itself is cute with comfy chairs and couches by a fireplace in one corner, high tables by the window for people watching, or the usual stools at the bar. Much better than going to the Cheesecake Factory across the street.

The Signature Lounge at the 96th
I debated putting this on the “To Eat” or “To Do” post, but I think I’m going to do both! It’s too amazing to not mention twice. While we were still dressed up from the fancy dinner we decided to go grab drinks at the Signature Lounge, which is located on the 96th floor of the John Hancock Building. Yep…96th floor. Luckily I had so much gum on hand this trip, my ears were popping every day with these crazy elevator rides! There are floor to ceiling windows everywhere in the lounge with views of the entire city and lake. Yes, even the bathroom had the views! We went at night and the lights were spectacular. Drinks were on the pricey side, but you’re paying for the view. If you go on a Friday night like us, expect a little bit of a wait to get seated and also expect a wait to leave. It seemed strange, but everyone has to go back down those same elevators we came up in, so make sure to give yourself time. There is a restaurant here too, The Signature Room, if you were more interested in food than drinks.

That’s it for the What To Eat recap! Compared to our recent Portland adventure I felt like we didn’t really eat that much, but typing it out I realize we did pretty good. Have you ever been to Chicago? Any recommendations for other places to try? I have a whole list of places we didn’t make it too…I think another trip is in the future! Don’t forget to check back later for some “To Do” recommendations!

~Stephanie