Exploring downtown Charleston colonial homes known as Rainbow Row

Must-dos for Exploring Charleston and Chicago

June 3, 2015
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A list of must-dos when exploring Charleston and Chicago.

Exploring downtown Charleston colonial homes known as Rainbow Row
This post was updated as of March 22, 2021.

There’s nothing like traveling to explore new cities. Even if you can’t travel far, there are gems within the United States. When it comes to exploring Charleston, South Carolina and Chicago, Illinois, consider us experts. For this reason, and for our love of these cities, we’ve put together a list of things you must do, places you must visit, and beverages you must try! Take it from us, you won’t regret it!

Exploring Charleston, South Carolina – What to Do

Charleston may seem like a sleepy little city to anyone from a bigger metropolis. But, don’t be fooled. The Holy City will work its Southern charm on you, and you will want to come back. When it comes to exploring Charleston, there are plenty of both free and paid activities to do. Of those, here are favorites.

  • Outdoor Activity: Wandering Downtown Charleston. The Farmer’s Market at Marion Square happens on Saturdays, and is open most of the year. If you’re already downtown on a Saturday, you can grab a quick bite to eat at any of the stalls. Once you’re done eating there, you are steps from shopping on King Street or walking over to The City Market. From the market, you can walk to the famous Pineapple Fountain. Then onto wandering the residential streets filled with colonial homes on and around The Battery.
  • Must Do: One thing you must do when visiting Charleston for the first time is go to the Angel Oak. There is a restaurant by that name, but in this case we mean the actual tree. Pictures do not do this giant oak justice. You will be amazed at its sheer size and beauty!
Pineapple Fountain at Waterfront Park in downtown Charleston
Angel Oak tree on Johns Island just outside of downtown Charleston SC

Exploring Charleston – Where to Eat and Drink

It’s hard to pick from the smorgasbord of local places all over the city. In fact, it seems like there’s somewhere new to try every month! (Not that that’s a bad thing.) With that said:

  • Restaurant: Husk is great restaurant for a modern take on Southern comfort food. Executive Chef Travis Grimes creates a fabulous menu using with locally-sourced ingredients. And their cocktails are just ::chef’s kiss::!
  • Sunday Brunch: Church & Union. Why? First of all, because Sunday brunch is a must (ask any Southerner). And on top of that, there’s the “Holy Sh*t Breakfast” menu option. It’s a plate piled high with Southern delicousness. We’re talking: fried chicken, biscuits, bacon, and donuts. Plus, it comes with your choice of mimosa or bloody mary. Be sure to bring a friend because it’s a two person minimum required to order. And if savory is not your jam for brunch, they also have Praline French Toast for you sweet tooth satisfaction. Need we say more?!
  • Bar: Prohibition has awesome and delicious cocktails. If you’re not in the mood for a cocktail, they have a great list of wines and beers too. If the name didn’t give it away, Prohibition has a speakeasy vibe. And with live music, you can sip and dance the night away!
Exploring Charleston restaurants 5Church brunch platter
Image Courtesy of Church & Union

Exploring Chicago, Illinois – What to Do

While Chicago has all the big city elements (size, history, tons of food, festivals, lots of cocktails, and so many things to do around the city) its people still have that midwestern charm! I.e. you can actually ask for directions and you’ll get an answer with a smile! So, if you must ask for directions, let’s give you somewhere to go:

  • Outdoor Activity:  One of the greatest outdoor design aspects of Chicago is the lakefront. And, one of its best features is the Chicago Lakefront Trail. It’s a jogging/bike path that runs 18 miles along the shore between the lake and the city. You could walk from the zoo to the Navy Pier and farther north all while taking in the city skyline.
  • Indoor Activity:  A museum! There are so many to choose from, but if we had to pick one, it would be the Art Museum. With so much to see, definitely give yourself an entire day. However, it’s still worthwhile even if you only have a couple hours. It’s silly, but if you go to the miniatures hall, let us know what living room you would want to live in!
  • Must Do: Something you must try to do when in town is spend an evening at The Green Mill. The Green Mill is a tiny, hole-in-the-wall, jazz speakeasy club. Al Capone frequented it way back when.  It has live jazz every day of the week, and the cocktails are to die for. Of which, we’d suggest the French 75.  It’s a classic cocktail with all things lady-like: champagne, gin, lemon, simple syrup, and a twist of lemon. Most days of the week it’s very serious jazz where you aren’t allowed to talk. But on Thursday, the big band takes over! There is dancing, loud music, everyone is yelling, and it’s exactly what it should be.
Chicago Illinois skyline with view of Lake Michigan and the lakefront trail
Image by Natasha T via Unsplash

Exploring Chicago – Where to eat and drink

As you can imagine, with a city the size of Chicago, it was no easy feat to narrow down options for places to eat and drink because there are so many fantastic options. Nonetheless, the challenge was on! Here are our top places to patronize for a bite or a drink.

  • Restaurant:  Le Colonial. Le Colonial serves upscale French-Vietnamese cuisine. The cocktails are also very good, but it was the fried egg rolls that gave them the win!
  • Bar: The Aviary. We’ll say it again: THE. AVIARY. If you want art in a glass, you must go to The Aviary. Each drink is so different, but so delicious. This cocktail lounge is run by the incomparable Grant Achatz, who has several other noteworthy locations. If you plan on going solely for the drinks (they do have a kitchen as well), definitely eat beforehand!
Porthole cocktail at The Aviary in Chicago Illinois
“The Porthole” cocktail trio from The Aviary where every sip is different


Obviously, there are so many places to eat, drink, and explore in both cities. This is just the tip of the iceberg. If you happen to find yourself in either Charleston or Chicago and you try any of the suggestions above, let us know in the comments what you thought!

Happy travels! xx


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