The Fall One-Two Punch
Produced by The Infatuation with
Polo Ralph Lauren
We define a One-Two Punch as a two-stop plan for dinner and drinks in the same neighborhood. And because pretty soon you’re going to have to drag a space heater with you anytime you leave the house, it’s best to be outside while you still can. Here’s a list of bars and restaurants within walking distance of one another, so you can enjoy the weather before all the trees lose their leaves, and the sun becomes a distant memory. As a bonus, most of these places have three-season patios with heaters so you can leave yours at home.
Giant in Logan Square is one of our favorite restaurants in Chicago, and has a frequently changing menu with consistently delicious food. But there are some classics that are always available, like the crab salad with waffle fries and tagliatelle with chili butter - both of which are must-orders. After dinner, take the scenic route to The Whistler and cut through Palmer Square Park.
This bar is a great spot to end your night with cocktails and some live music. Most drinks are $10 and under, which means you can hang out at the bar until close and still be able to pay your rent on time.
Winter will mean approximately 18 hours of darkness per day, so it’s important to take advantage of any sunny fall days while you can. Do this by going to Arepa George in Humboldt Park for delicious arepas or a tasty empanada. Then (unless the temperature has dropped 30 degrees since you ordered your food - which, in Chicago, is entirely possible) walk through Humboldt park to Cafe Marie Jeanne for some drinks or a glass of wine.
Cafe Marie-Jeanne is a relaxed all-day French cafe in Humboldt Park with a long bar and Happy Hour daily from 3pm-6pm. This place is never insanely busy, and is a great low-key option for post-dinner cocktails or wine. Plus, the bar has has plenty of outlets, so you can always bring your laptop and finally finish your novel about a vampire au pair and werewolf farmer falling in love in the French countryside.
Hopleaf in Andersonville is a restaurant with an extensive beer selection and great food. The CB&J (cashew butter and fig jam) sandwich, duck reuben, and steak frites are all standout dishes. The food is heavy, but a brisk walk to Pearl’s Southern Comfort will help you forget that you just ate three servings of housemade potato chips.
Ok, so technically Pearl’s isn’t in Andersonville - it’s on the border of Edgewater - but it’s a short walk through a pretty tree-lined area. The atmosphere doesn’t hit you over the head with it’s New Orleans theme, with large TVs that make this place great for watching sports. Sit at the bar and sip on a Sazerac that’s perfectly color-coordinated with the fall leaves.
Somerset in the Gold Coast is one of the best restaurants in the entire city, and it’s good for a special occasion but also just a nice night out. The American menu is versatile enough to please everyone, with dishes ranging from an excellent smoked beet tartare to delicious pastas to perfectly roasted chicken. The space is upscale, with non-kitschy nautical touches, and there is a large heated front patio overlooking Mariano Park.
After eating at Somerset, take the short walk through Mariano Park towards Gibsons. Sit in the more casual bar area for a martini and cartoonishly large desserts like the Macadamia turtle pie, or carrot cake. They’re literally six pounds, and a great way to prepare for your upcoming winter hibernation.