Chicago is a big, spread out city and if you have a limited time there, you certainly only want to hit THE best spots. One of the worst things while traveling is when you only have 6 precious meals in a city, and you find yourself wasting one of six at a mediocre, super forgettable, overrated, grade B restaurant. So here's my list of Chicago's must-explore neighborhoods, cool hotels, buzzing rooftop bars and the yummiest restaurants. Coming from San Francisco, my bar is high, yet my criteria is simple: great atmosphere, dreamy design and delicious food/drinks!
Lunch: Avec is a very hot Mediterranean restaurant right now. It's on a lot of people's must-visit list. The hummus plate was absolutely gorgeous, and oh my god... the pita bread! If you go for nothing else, do it for the pita. It's made to order and comes out fresh and piping hot. Just go ahead and ask for extra pita bread when you're putting your order in.
Dinner + Drinks: Write Sushi Dokku on your list for dinner, now star and circle it. Not only is their sushi SO DELICIOUS, the West Loop restaurant has an underground bar, just below the restaurant, that serves lip-smacking, Japanese-inspired cocktails that are absolutely NOT to be missed. So after really tasty sushi, head downstairs for a night cap. This dark and hip spot is home to the best meal and drinks I had in Chi-town!
Drinks: To be honest, Cindy's rooftop in the Chicago Athletic Association is awesome for really, anything — happy hour, sunset drinks, brunch. After seeing just how many people line up at it's door, it's clear that it's the hottest place in town. The drink menu, open-air design, plus view of Millennial Park are it's shining moments. Drinks, or "potions" as their called, are very inventive and include fun ingredients like kombucha and activated charcoal. It's highly recommended to make reservations ahead of time because the wait can be hours long!
Hotel: Speaking of Cindy's, the Chicago Athletic Association hotel (CAA) is a really, really cool, historic landmark hotel. For decades, it was a private men's club and was recently renovated and restored by hospitality design genius' Roman and Williams (they also are known for the ever-popular Ace Hotels). It's restored original details are stunning and have so much history to them. The lobby is dark and moody and has free public wifi, which makes it a great place to work for a few hours. There's ton to check out: Shakeshack is on the ground floor, it's home to a 8-seater micro bar for REAL spirit connoisseurs, the Cherry Circle Room restaurant and of course, Cindy's. All to say, even if you don't stay here, it's a must visit!
Brunch: The Robey Cafe which is located on the ground floor of The Robey Hotel has AMAZING brunch. The loaded Crab Avocado Toast and Pancakes were both mind blowingly good. I was very impressed by the brunch menu, so can only imagine that other meal times are just as delicious. The Robey also has a trendy, hipster rooftop bar, with a pool. If you find a quiet corner, it's a good time.
Work: Soho House Chicago is obviously a cool hang. It's known for it's super Instagrammable decor — think velvet peach sofas, crystal chandeliers and vintage vibes. The lobby is a pleasant and comfortable place to pull out your laptop, or meet someone for coffee, and stay a while. Staff won't push you out so you can stay as long as you want, and good thing because the people watching is prime!
Coffee: I'm a loyal La Colombe customer and there are a handful of La Colombe cafes in Chicago. Coming from the West Coast, it's pretty novelty, yet consistently good coffee, and how can you resist their adorable cups and saucers?! Anytime I'm in a city with La Colombe, I add it to my map. NYC and DC are still my fave locations, but if you're looking for a good cup of jo, this is your spot.
Neighborhoods: Lincoln Park is a more affluent neighborhood and really great to walk around. It's main avenue, Armitage, is lined with beautiful trees and boutique shopping. Chicago's own Jeni's Ice Cream is kind of a must. Jayson Home and Interior Define (two shops that are unique to Chicago) are in the area. I also enjoyed walking around Logan Square. You don't need more than an hour or two there. It's a small, mostly residential, hipster-ish hood with beautiful houses and a few stretches of restaurants and bars. If you have time, visit!
Happy travels!