Travel Fanboy

TFB #8 – Chicago City Guide

Become a Patron!

In this episode, I take you to Chicago and give you the scoop on some of my favorite spots in my hometown. There’s no way to discuss every little great spot in the city, so I focus on a few great dining and drinking experiences. Be sure to listen to the entire episode, because I give my buddy Han a call and he provides us with some quintessential Chicago eateries.

Here we go:


Girl and The Goat

A true dining experience. Head chef, Stephanie Izard, was the first female chef to win Bravo’s Top Chef competition. It’s located in the Randolph Restaurant Corridor in the West Loop. The menu features a rotating list of craft beers and cocktails. The imaginative menu is for those looking for some bold flavors and something unique. They are shareable plates, so grab some people you trust.

Gibson’s Steakhouse

We go from distinctive to classic. Gibson’s will celebrate its 30th anniversary of being a Chicago staple in 2019. There’s a reason for the steakhouse’s permanence, the beef is some of the best you’re likely to ever have. Gibson’s has its own USDA Certified Angus Beef Program. I have no idea what that means, but I’m sure it’s good. Sully up to the understated bar before indulging in the unapologetically big portions at dinner.


Locally famous head chef, Sushi Mike, serves what is likely the most delectable rolls in Chicago. It’s in one of my favorite neighborhoods, Andersonville, and is a BYOB. It’s a spot where it’s fun to go off book. Just tell your server your favorite cuts of fish and flavors and Sushi Mike will whip you up something amazing.

The shiitake roll.

Boiler Room

This trendy Logan Square restaurant with a dive bar feel serves up non-standard pies. If you’re looking for a break from the multiple inches thick deep dish delights, BR has an array of interesting topping choices, including the surprisingly good beet prosciutto. Its patio makes for a great summertime spot. For those on a budget, the pb & j special is sure to win you over. For $10, you’ll get a slice of pizza, a shot of Jameson, and a 16 oz PBR to wash it all down.  


The Violet Hour

In the hipster neighborhood of Wicker Park (is it still hipster-esque?) you’ll find, with a little searching, the pre-prohibition style speakeasy known as The Violet Hour. To find it off of Damen, just look for a big mural and people lining up to seemingly nowhere. Inside you’ll be treated to delicious cocktails and unique ambiance.  

The Milk Room

Expensive cocktails made with rare ingredients. This great join for whiskey lovers is on the second floor of the Chicago Athletic Association. It’s a small bar, only seating 8 at a time and the drinks aren’t cheap, but you’re likely to remember every sip. Reservations are needed and only two seats can be had. You’ll have to cough up $50 to reserve your two-hour block, but it goes towards your final bill.


Another Andersonville hotspot, but this one is great for beer lovers. The food menu is Belgian inspired, but their expansive draft list is sure to satisfy those with discerning tastes.


Millennium Park

I love the Park Grill and outdoor Plaza space. Great location in the summer to hang out, have a few drinks, and catch some live entertainment.

Navy Pier

It’s a tourist trap, but it’s our tourist trap. Shopping, restaurants, a theater, lake cruises, and more. Great for kids, especially with the summertime fireworks.

Museum Campus

A beautiful green space near the lake which houses the Shedd Aquarium, the Field Museum, and the Adler Planetarium. If you’re a Bank of America cardholder, you can get in for free on the first full weekend of every month at Adler and the Shedd (Sunday’s only). Although not on the Museum Campus, free access is also available at the fantastic Art Institute of Chicago.

If you have a favorite restaurant, bar, or activity in Chicago, please let me know!

Travel Fanboy

Adam is the editor of and Beyond being the world's most famous travel influencer, he's passionate about reckless points and miles pursuits. Formerly of Vegas Fanboy fame.

Add comment