Below is my guide to navigating one of my favorite cities in the world! For even more recommendations check out my map here. My go-to app for finding fun things to do and places to try is Sosh! Enjoy :)
EATING & DRINKING
Bakeries & SweetsBakery and restaurant by day, late night diner by night. Little Goat has it all. On the side of Little Goat is Little Goat bread where you can find freshly baked bagels, unqiue breads and pastries. If you’ve ever been to Balthazar in New York, it’s very similar but swap the French food for upscale diner food that’s open from the crack of dawn until 2 a.m. The head chef was a previous winner of Top Chef, too! A cafe and cute little grocery with a bakery upstairs. You can stop in and stay for brunch or just pick up some baked goods and treats on your way along Southport for some great shopping. They make gourmet cupcakes, scones and special a “savory” muffin with an egg inside that is scientifically confusing, but completely delicious. A delicious and delightful little cupcake shop that has some of the best cupcakes in the city – and Chicago is not short on cupcakes, that’s for sure. They also stock other treats as well and if you’re a local and are looking for a great spot to order a cake, this is the place!
Think Sprinkles on steroids. If you think Sprinkles has creative flavors, wait until you try Crumbs — and they’re probably twice as big so plan on sharing with a friend… or not! :)
Known for their mixology team, you’ll find some of the best cocktails in the city at Sable. It’s very close to the Michigan Avenue and River North shopping scene as well making it very convenient to drop in and rest your tired feet. The Aviary is one of the most innovative drink places you’ll ever experience. They treat cocktails the way that 5 star chefs treat their dishes – with precision & creativity. If you’ve never had a drink that came out with a Bunsen burner, dry ice, or in a cornucopia you should plan to make a stop here. If you like speakeasy type cocktail lounges, this is the place to go. For a very Mad Men-esque cocktail experience, head to the Pump Room. It’s located in one of the trendier hotels in the city, the Public Hotel, which was created by the very same man who co-founded Studio 54. The service, food and drinks are all superb with simple yet modern and elegant decor to match. The summers are what everyone lives in Chicago for, and the rooftop bars are where everyone flocks as soon as the sun comes out to play. This particular rooftop bar has a fantastic view of Downtown and the lake. They mix up amazing cocktails (some that they literally light on fire) plus it’s conveniently located near Michigan Avenue & the heart of the best retail therapy in the city. Venture over into Wicker Park for one of the most unique cocktail settings in the city – inside The Bedford you’ll find yourself in a real bank vault sipping on your drink of choice. You can even open the safety deposit boxes and if you have a pen and paper leave a note behind for someone to discover down the road once your trip is over.
Best Watering Hole
(River North) You’d probably miss this tiny dive bar walking down Chicago Avenue, especially when you see the giant Chick-Fil-A sign that you might be flocking to, but it’s a fan favorite of the locals in River North. Complete with life size jenga, a pool table, a ping pong table and a tiny DJ booth with matching dance floor, Streeters is an incredibly entertaining dive that you’ll be hard pressed to not have a good time at. (Old Town) If you’re looking for a fun place to watch a sports game and are fan of unique beers, Old Town Pour House is fantastic. There are gigantic TV’s that line the wall behind the bar and in front of them are an equally impressive span of beers on tap. The daytime sports game and drinking scene will quickly transition into a hotspot at night in the area. (Lincoln Park) There’s a reason why the Blackhawks love this place and why Kid Rock makes a point to drop in when he’s in Chicago. This neighborhood dive bar serves up an all you can eat brunch in the mornings, plays sports games on TV during the day, and has DJ’s spinning everything from Katy Perry to Jackson Five, The Temptations, and Britney Spears at night (and until 3 a.m. on Saturdays). It’s a total blast and quite the experience for anyone seeking a late night impromptu dance party. Not to mention, it’s my favorite bar in the city! :) (Wicker Park) If you are over in Wicker Park and enjoy a good video game or two, check out Emporium. It’s the best arcade bar in the city and has a plethora of games that will take you back to your childhood or your kids childhood. Stocked with Mario Brothers, Paper Boy, NBA Jams and Street Fighter, this BYOF (bring your own food, they don’t care!) and full bar gaming haven is a great time. (Lincoln Park/Lakeview) Tucked away in the northern part of Lincoln Park and the southern part of Lakeview, this is a fun bar to grab a beer and watch sports or hang out with friends. There are TV’s everywhere. If you’re in a booth at the front there are 2 TV’s in the wall next to you sitting and one larger one above it to ensure that you can catch what’s going on at all times. They also have their own beer garden in the back, which is great when the weather is nice.
SHOPPING & CULTURE:
Green Goddess Boutique
Must Visit Spots
- The Bean — hands down the most photobombed spot in the city, but I swear everyone looks good in pictures at The Bean
- Hancock Tower — go to the top floor and you’ll get a free, 360 degree view of the city while sipping on cocktails at The Signature Room
- Willis Tower (formerly Sears Tower) — if you have the time head to the top of the Willis and take the tour to learn interesting facts about Chicago and dare to step out on the Skydeck, the clear ledge that overhangs the city 103 floors up
- Navy Pier/River Tour — a must if the weather is nice, they will take you through the architecture and history of the city on the river and depending on the tour will speed up and down the lake for epic views of the skyline, try Wendell or Rocketboat
- Lincoln Park/Zoo (it’s free!) — a fun stop that’s easy on the wallet to enjoy the animals or a wonderful stroll through the park
- Shedd Aquarium and Field Museum — right next to each other and you can buy a pass for both, the Shedd overlooks the lake with an infinity pool backdrop that is one of the cooler things you’ll see at an Aquarium
- Wrigley Field — for those who appreciate references made in the movie Rookie of the Year or who can’t leave the city without a true Chicago hot dog at a Cubs game.. if you have time take the tour!
What to wear
When to go
Where to stay
- Waldorf Astoria
- Four Seasons
- Hotel Raffaello
- Sofitel Chicago Water Tower
- Park Hyatt
- Public Hotel
- Embassy Suites
- Hilton Garden Inn
- Marriott Courtyard
- Fairfield Inn
- Residence Inn
- Hampton Inn
- Holiday Inn Express