It's no secret Chicago winters are brutal, but in a strange way, cold brings us together. During colder months, people tend to stay inside more which means more movies, good eats, and time for family and friends. I've even heard that the winter months can bring out closer relationships between friends, and maybe even a romantic interest (#cuffingseason). And the best way to bond? Food. 

Heads up! If you're looking for the healthiest places to eat in Chicago, this is the wrong article. But hey, these places are sure to raise certain levels of nostalgia and strong childhood or non-childhood memories. Or if your sweet tooth just gets stronger in the winter, keep scrolling. Here are the best Chicago restaurants for getting us through winter. 

1. Cheesie's Pub and Grub

To Chicagoans, Cheesie's has become a favorite pastime. I mean, who doesn't love a good twist on the American classics of mac and cheese with grilled cheese? Trust me when I tell you that a sandwich with these two childhood classics is sure to remind you of all those cheesy family memories. They have various locations due to their popularity, you can go to their website to find the closest one to you in the Chicago area.

2. Toast

Located in the charming Lincoln Park, Toast is home to the most creative and delicious breakfast food. Dishes like Elvis Pancakes (pancakes with bananas, pretzels, chocolate chips, powdered sugar, and cool whip) or the Breakfast Burger (grilled beef patty with prosciutto, fried egg, arugula, and pesto mayo on fresh french bread) will be sure to keep you on your toes.

Breakfast food is commonly associated with happy memories, and this place is full of nostalgia. I was once told that breakfast is the best kind of pregame for your day, so stop by Buck town or Lincoln park this winter to start your day out right.

3. Portillo's

It's hard to talk about Chicago food without including Portillo's. It's a classic. Get yourself a Chicago style hot dog and reminisce about those hot summer Cub's games, or pig out on the famous chocolate cake that us Chicagoans can't seem to stop talking about. However, If you have a bad case of the winter blues, go for the Cake Shake. I've never seen anything like it, because it's literally how it sounds. Cake in a shake. My two favorite things in one and I don't think anybody is complaining. 

4. Lakeview Kitchen and Market

Lakeview Kitchen and Market offers a wide variety of sweets from various desserts such as cookies and brownies. Just click the play button and you will be instantly transported back in time to your grandma's house eagerly waiting for a cold cup of milk and warm cookies. It has the perfect consistency of crunch on the outside and all that ooey gooey dough on the inside. Plus, this place offers cooking classes which serves as the perfect winter activity to refine those culinary skills.

#SpoonTip: Click here to sign up for a class or here to view the rest of the menu!

5. Mindy's Hot Chocolate

Nothing pairs better with winter than good old hot cocoa. Mindy's has the best cup of hot chocolate in the city. It's the perfect way to warm up after skating at Millennium Park or shopping down State Street. The hot chocolate flavors range from peppermint to Mexican, so your hands will be sure to stay warm around that cocoa mug all winter. 

6. Eataly

Holy Cannoli! Take a mini trip to Italy right in Chicago at this place. Let's face it, Italian food and culture are some of the best in the world. Without having to fly all the way to Italy, try some cannoli, fresh pizza, or pasta at Eataly. The coolest part is that it's also a store—the olive oil and wine are fresh from Italy so your dining experience does not have to stop once you leave. 

7. Nutella Bar in Eataly

Anyone with a sweet tooth for Nutella will be in heaven at this place. It's a mini cafe serving Nutella-filled foods such as crepes, gelato, coffee, and on croissants! It is conveniently located on the first floor of Eataly. Nutella lovers will experience Nutella in a whole new way. 

8. Sarkis

While there may be a debate on how to pronounce this place, (Sar-kees vs. Sar-kiss) there is no question the Bacon Loretta is delectable. It consists of bacon, melted white cheese, tomatoes, onions, and mayo wrapped up in french bread. Trust me when I say this combination is adored by the people of Chicago. Paired perfectly with a side of hash browns and ketchup, and this is the perfect recipe for a food coma... or a nap.

9. Insomnia Cookies

This place is a godsend in many college towns around the country, but the one located in Evanston has impeccable service, variety, and an overall high quality place. There's something about a restaurant that delivers milk and warm cookies to your door that I just can’t get over. After long nights out or just random late night cookie cravings, this is bound to fill you with nostalgia for grandma's homemade cookies. Or it might just bring out the late night munchies.

10. 3 Arts Cafe at Restoration Hardware

This grilled cheese is sure to bring up some nostalgia of your glory days on the field or playground and chowing down on one of your parents' classic grilled cheeses. 3 Arts Cafe easily has the best grilled cheese you will find and it's located right in the Gold Coast. This place usually has a wait, but it is located in a super bougie furniture store that brings your Pinterest dream house to life.  

11. Lady Gregory's

Lobster Mac and Cheese? Yes please. Lady Gregory's screams comfort with its baked cheesy noodles and buttery chunks of lobster, topped with a truffle cream sauce and crunchy corn bread crust. They also have amazing appetizers like avocado toast, artichoke dip, deviled eggs, truffle crisps, and many more. YUM! The restaurant is located in both Andersonville and Old town. Check out the rest of the menu here. (They even have brunch and gluten free options!)

12. Sweet Mandy B's

You'll understand why the slogan is "the best things in life are sweet" as soon as you walk in. This heavenly bakery on Webster street is known for their old-fashioned desserts. Serving cupcakes, pies, cakes, and cookies, you'll see why this is named the #1 Bakery in Chicago by several food critics. Make sure to try the butter cream frosting! 

13. Tavern at the Park & The Tree House

If you want comfort food but you're not sure where to start, then Tavern at the Park has the perfect variety for you. From mashed potatoes, French onion soup, Brussels sprouts, wings, calamari, and flatbreads, this place has become a hot spot, especially during those long winter months. Right in the heart of Chicago, Tavern at the Park is right across from Millennium Park. It offers a nice break from the hustle and bustle from the city, while providing dishes like Steak burgers, various fish dishes and some classic Mac and Cheese.

14. Giordano's 

It's hard to talk about Chicago food without mentioning Deep Dish Pizza. Made with only the freshest ingredients, Giordano's is the Italian place to go. Just ask any of the Blackhawks players—I have seen about nine there during my lifetime of eating at this famous pizza place.

15. Italian Village

I had to save the best for last—Italian Village. This one is a personal favorite, being the oldest Italian restaurant in Chicago and my family's go to for family winter dinners. We have tried many Italian places and I can guarantee you will not find better food or service than this place.

When you walk in, it looks like you're dining in a little village in Italy (hence the name) and the twinkly lights really add to the ambiance. Honestly, everything on this menu is fantastic, but for the ultimate food coma, order the chicken Parmesan, chicken Vesuvio, or the classic spaghetti and meatballs. This place also has an incredible selection of Italian wine. For our 21+ readers, wine not give this a taste paired with that pasta?


Whether you're a true Chicagoan, a suburban, or a visitor, try these tasty treats to get through another brutal winter. The weather may be freezing, but like I said, it does form close relationships throughout all cultures. Nothing beats sharing a love of chocolate, cheese, bread, or whatever that guilty pleasure is than pigging out with some pals.