It’s been years since I visited the windy city—around fifteen years as a matter of fact. Having last been as a child, I was incredibly excited to now experience the Windy City as an adult.

Over several trips to Chicago, I’ve taken the famous river architecture tour, experienced the electric energy at Wrigley Field, had play time at the Museum of Ice Cream, and dined at great restaurants, many of them Black owned. Here’s a guide to get you started on experiencing the best of Chicago.

Best Time to Visit

I’ve been to Chicago in every season, and it has personality year-round, but each season has its own vibe. Chicago winters can be harsh, and you run the risk of getting snowed in, but Summertime Chi is unmatched, so I strongly recommend visiting from around May to September. There are plenty of events and festivals to get into, patio dining, fireworks at Navy Pier and more.

Getting Around

Chicago is one of the most transit-friendly cities in the U.S. and despite much of the propaganda we’ve heard all our lives, there are several safe and walkable areas in the city. Here’s how you can get around:

The L (CTA) will get you almost anywhere.
Ride-shares are plentiful and easy to get.
Walking is easy in the downtown neighborhoods and along the lakefront.
If you’re flying in, O’Hare and Midway both connect directly to the train system.

Ideal Photo Spots

If you’re traveling solo and want great shots, try:

Riverwalk for architecture and water backdrops
North Avenue Beach for skyline views
Skydeck Chicago or 360 Chicago for city views
“The Bean” or Cloud Gate at Millennium Park (pictured below)
Wrigley Field

*“The Bean” or Cloud Gate at Millennium Park*

Food & Restaurants

Chicago is known as one of America’s best foodie cities, even ranking ahead of other large cities like LA and New York. There’s no such thing as leaving Chicago hungry. The city is known for:

Chicago-style hot dogs
Deep dish pizza
Italian beef

These meals and so many others make the city a wonderland for someone who loves to try food. Check out some of my favorite Black-owned Chicago restaurants or consider the restaurants below!

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, and from friends and family, and I always wondered if it was really worth all the hype. I finally tried it, and I think it’s worth it. The mild sauce is unlike any other sauce I’ve tasted, so it’s difficult to describe, but you should know that it’s delicious. There are several Harold’s locations, especially across the Southside, and I’ve heard some are better than others, but I do feel like the most important thing to know is that I don’t think you can have the wings without the mild sauce—the two go hand in hand.

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 at all 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 also great, and a super refreshing ginger lemonade. As much as I’d love to try the other restaurants in Revival Food Hall, this is a spot I always revisit.

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 did the trick. I ordered the fried catfish po’ boy and fries with a side of hot honey sauce and garlic butter sauce for dipping. 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 always stayed, which is the Cambria Hotel Chicago Loop-Theater District. It cannot be a more convenient place to get to this Chicago staple. When it comes to popcorn, I can be a kind of traditional girl, so the first of many times I’ve been to Garrett’s, I went for the classic kettle corn, which was the perfect 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.

Things To Do

Chicago has plenty of things to do, which is part of what makes the city so great. I’m linking out to a fuller guide, so you get a feel for some of these activities. Here are a few must-dos to get you started:

Explore the Riverwalk
Visit Millennium Park and “The Bean”
Walk along Navy Pier
Take an architecture boat tour
Visit a museum (Art Institute, Museum of Science & Industry, etc.)
Wander a neighborhood like Pilsen, Bronzeville, Wicker Park, or Logan Square

Architecture Tour

I first booked a Chicago Architecture River Cruise through Trip Advisor because it is always one of the most recommended sightseeing activities. I have been in both the fall and the summer and strongly recommend doing this activity in the summer when the weather is nice. If you happen to be visiting in the fall and want to do the boat tour, I suggest really bundling up as Chicago is very cold in the fall and winter, and it’s even colder on the water.

The hope is that you get a really good docent for your tour who is really knowledgable about 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 about $45, I would say the tour is worth it for a view of the city and a ride along the river walk.

Quick Tips for Solo Travelers

Chicago is a big city, but it’s also one of the friendliest and most hospitable cities I’ve ever been to. People will talk to you, and if you need help, they don’t mind offering it. Stick to well-lit areas at night, keep your belongings close on trains, and trust your instincts like you would anywhere else. Neighborhoods like River North, the Loop, West Loop, and Lincoln Park are comfortable for solo exploring, especially if you’re walking or using transit.

Chicago is fairly easy to navigate, the food is incredible, and there’s always something happening, which makes it a great destination for any kind of traveler.