A Guide To Chicago, Illinois

It’s been years since I visited the windy city- around 15 years as a matter of fact. I’ve accepted a new position that will bring me to the city from time to time so this is both a travel diary and an evergreen itinerary of sorts. Having last been as a child, I was incredibly excited to now experience the city as an adult.

In my short trip, I took a river architecture tour, tried at least a couple Chicago food staples like Harold’s Chicken Shack and Garrett Popcorn, and even attended opening night of Wicked on Broadway. Keep reading to take a dive into my trip.

Restaurants

Chicago has become known as one of America’s foodie cities, even ranking ahead of other large cities like LA and New York. It boasts a signature deep dish pizza entree, Italian beef, barbecue and other notable dishes that make it a wonderland for someone who loves to try food. I didn’t have much time to embark on the sort of food tour I’d love to do in a city like this, but trust me, I’ve got plans for my return. For now, check out the spots I did visit.

Harold’s Chicken Shack

Mild wings from Harold’s is a meal i’ve been hearing about for years in rap songs, on social media, from friends and family and I always wondered if it was really worth all the hype. It is. The mild sauce is unlike any other sauce I’ve tasted so it’s difficult to describe. What i’m trying to say is, you need to try it for yourself. There are several Harold’s locations, especially across the Southside and some i’ve heard are better than others, but most important is making sure to get the wings with mild sauce.

The Fat Shallot

For lunch one day, I stopped by The Fat Shallot in Revival Food Hall and I went back and forth between ordering the buffalo chicken sandwich and the truffle BLT. At the last second I decided on the truffle BLT and I was not the least bit disappointed. With crispy bacon, avocado, arugula, tomato, truffle aioli on thick cut challah, I can definitely say it’s the best BLT i’ve ever had. As a complement, I also had both the truffle fries and the spicy sesame fries, which were outstanding, and a super refreshing ginger lemonade.

As much as I’d love to try the other restaurants in Revival Food Hall, I’m equally as excited about going back just for this particular meal from The Fat Shallot.

Ina Mae’s Tavern

Ina Mae’s Tavern was recommended to me for New Orleans style food. I have to say I was skeptical because food in NOLA is truly incomparable, but the meal I had here sufficed. I ordered the fried catfish po’ boy and fries with a side of hot honey sauce and garlic butter sauce for dipping and then two delicious Arnold Palmers. It’s a small restaurant with a very homey feel, which is definitely my vibe, and the service was great. If you get a craving for NOLA inspired food while in Chi City then this may be an option for you.

Garrett Popcorn

Garrett Popcorn was just a few steps from where I was staying; I could not have been in a more convenient place to get to this Chicago staple. When it comes to popcorn, I can be a kind of traditional girl so I went for the classic kettle corn. It reminded me so much of one of my favorite Virginia treat shops Uncle Dave’s Kettle Corn. The kettle corn was just the right amount of sweet and salty. I had it as a snack just before seeing Wicked on Broadway and, without shame, I also ate the rest of it for breakfast the next morning.

Other restaurants to try

Because i’ll be visiting Chicago often now, I solicited restaurants from several people that I could try each time I go. I wanted to include them here so that you’ll have them as well.

Ja’ Grill (Jamaican)

Fremont Chicago

Maple & Ash

RPM Seafood Chicago

STK Steakhouse

Spirit Elephant (Vegan)

Mastro’s Steakhouse

Hometown Coffee & Juice

La Chapparita (Tacos)

Luella’s Southern Kitchen

Parson’s Chicken and Fish (Soul Food)

Au Cheval (Burgers)

Smoque BBQ (Barbecue)

Honey Butter Fried Chicken (Sandwiches To Go)

Architecture Tour

I booked a Chicago Architecture River Cruise through Trip Advisor because this it was one of the most recommended sightseeing activities and also one of the only activities I could make work for my schedule. It was quite chilly out there on the water, so I imagine the weather is much more enjoyable in the summer, but as far as the architecture, it was stunning. I wasn’t quite sure what to expect in the way of a tour guide, but the docent for my tour was quite knowledgable on the history and engineering of the buildings. If it means anything to you, there is also a bar with both alcoholic and non-alcoholic drinks as a bit of a treat while on the tour. At just $45, I’d say it’s worth it for a view of the city and a ride along the river walk.

Other Recommended Activities

Lincoln Park Zoo (Free)

The Art Institute of Chicago ($25)

Chicago 360 Observation Deck ($45)

Navy Pier (Free)

Garfield Park Conservatory (Free)

Brookfield Zoo ($25)

Shedd Aquarium ($40)

Aside from the horrific traffic, I loved Chicago as a city and i’m thrilled about the opportunity to visit often. I’ve got an extensive list of activities and restaurants to shape each of my future trips, and i’ve shared them all with you here so that we can experience the city together.