Mac & Cheese

I’m a native Wisconsinite, so when the weather starts to get a little chilly, I’m all about the comfort food. Lucky for me, Chicago restaurants are never in short supply of some of my favorite dishes. For those of you traveling and feeling a little out of place, take a moment to wander over to any of the below restaurants and grab a bite to eat. Hopefully, it’ll remind you a bit more of home. Here are a few of my favorite comfort foods, but they only skim the surface of what Chicago has to offer.


Paris Club

Daddy Mac
Matilda’s (3101 N Sheffield Ave)

As for the Daddy Mac goes, give me cavatappi noodles with the right blend of cheese and smoked bacon and we can call it a day. They blend together cheddar, mozzarella, provolone, smoked gouda and shaved parmesan and serve it with chipotle peppers. I'd opt out of the peppers and add in some chicken (because protein makes this dish healthy-duh). This is my favorite mac and cheese in the city. If you’re looking for an appetizer before you indulge in your Daddy Mac, I’d suggest the goat cheese and marinara dish. It’s simply divine.

Hearty Beef Stew
Soupbox (50 E Chicago Ave, 2943 N Broadway St)

I’m such a sucker for beef stew and Soupbox never disappoints. Honestly, you could probably get just about any soup here and be in love with it. However, I would suggest getting the Hearty Beef Stew and save ¼ of your bowl to add in Cream of Potato & Leek. The perfect blend of beef stew with potato soup. Sold.

Green Door Tavern (678 N Orleans St)

I used to work just around the corner from GDT and I can’t tell you how many times I ordered their chili. I’m not even that person who grew up loving chili. I didn’t start eating it until about three years ago and I’ll tell you what, I love the chili from GDT. Good old fashion chili with a side of kidney beans, red onions, jalapenos and garlic bread. A cup is big enough for one, a bowl you could split with at least two people.

Shepherd’s Pie
Corcoran’s (1615 N Wells St)

I’ve been on a huge shepherd’s pie kick lately and this is the only one I’ve had in the city that seems to satisfy. An Irish restaurant serving up quality Irish grub, you can’t be surprised. The amount of flavor in this dish and the heaping mound of mashed potatoes that top it off, it leaves me nothing but happy and totally stuffed.

Chorizo-Stuffed Potato Skins
Wells on Wells (1617 N Wells St)

If you’re in Old Town and you think the shepherd’s pie might be a bit much to handle, head next door to Wells on Wells and order the Chorizo-Stuffed Potato Skins. I’ve had a lot of potato skins in my day, but these tickle more taste buds more than anything else. They don’t leave you feeling like you just wiped grease all over your body either, so that’s always nice.

Rotolo Primavera
Filippo’s (2211 N Clybourn Ave)

This is my secret dish and I’m sharing it with all of you. This is my favorite dish I’ve ever eaten in this country (write it down). I love Italian food and Filippo’s Rotolo Primavera is the most succulent blend of light rotolo pasta, stuffed with ricotta, spinach and prosciutto served in a light pink sauce. Don’t make me regret sharing this with you, please treat this dish with respect and you can thank me later. 

Short Rib Bourguignonne
Paris Club (59 W Hubbard St) 

Last fall I was on a big French food kick and when I came across the Short Rib Bourguinonne at Paris Club, I was in heaven. This dish is served with your typical root vegetables and the meat falls apart in your mouth. It is so savory you might find yourself licking the plate clean.



Parmesan French Fries
Merkle’s Bar & Grill (3516 N Clark St)

My friends and I call Merkle's French fries “crack fries” because they are so addicting they should be illegal. OK, maybe not illegal, but just know that you’ve been warned. They are amazing.

Tator Tots
Brownstone (3937 N Lincoln Ave)

If I plug french fries, I have to plug its counterpart, the tator tot. If you can’t tell already, I love potatoes, but this is my last potato plug, I promise. I just had these the other day and they have great seasoning and are not overly greasy so you don’t feel as bad about yourself after ordering a side and eating the whole I’ve heard.


Chocolate Cake

Chocolate Cake
Portillo’s (100 W Ontario St)

I know Portillo’s is known for their hot dogs, but you guys, they have the most amazing chocolate cake. Trust me when I say that this is possibly the best chocolate cake you will ever have. You might also want to go for a 7 mile run before you eat a piece to offset the calories, but it’s totally worth the sweaty recovery. 

Chocolate Cheesecake Cupcake
The Twisted Baker (1543 N Wells St)

This little bakery is easy to miss as you walk down Wells St, but keep your eyes open and stop in. They ice the cupcakes fresh for you and words can’t describe how amazing the frosting is. Oh, and don’t even get me started on the cupcakes themselves. I’m recommending the Chocolate Cheesecake Cupcake, but honestly, go for whatever floats your boat. This is one of my new go-to bakeries.

Alright folks, that about does it for me. I could go on and on, but I'll leave this list for now. I know there are so many more amazing dishes out there, so if you have a few favorites to add to the list, please do so in the comments section! I'm always looking for more places to satisfy my comfort food cravings. Enjoy!