Blog post

Weekend Guide to Chicago

May 7, 2018

The Windy City blew me away, both literally and figuratively speaking. My trip to Chicago made me fall in love with big cities all over again, and reminded me of why I used to live in one (New York City). Don’t get me wrong, I absolutely love living in Charleston-there is no charm like southern Lowcountry charm, but there’s something magical about the energy that pulses through a big city.

Prior to my trip, I spent hours researching the must-dos, the must-eats and the must-sees, and mapping them out so that everything fit into our 72-hour itinerary just so. Below are my recommendations for a long-weekend getaway to Chi Town. ]
Disclaimer: We did not try all of the “Rooptop Bars” or “Best Lunch Spots”

What to See:
“The Bean”
Navy Pier
Magnificent Mile
Lincoln Park/Lincoln Park Zoo (Public park with free admission into the zoo)
Oak Street Beach (For a very cool view of Lake Michigan and The Chicago Skyline)
Wrigley Field

What to Do:
Chicago Architecture Boat Tour (I recommend Chicago Line Cruises because they offer a great Groupon and provide complimentary cookies, coffee, hot chocolate and tea on-board)
Rent a bike through Divvy, Chicago’s bike share program, and bike through Lincoln Park and along Oak Street Beach (Buy the $15 Explorer Pass for the day, it’s worth it)
Stroll down Magnificent Mile (Michigan Avenue, which has excellent shopping, but also great for simply sightseeing and people-watching)
See a comedy show at The Second City, or any comedy club in Old Town
(Fun Fact: The Second City is the birthplace of many famous comedians/actors)
Visit Wrigleyville – see a Cubs game if they’re in town, but if not take some time to explore the borough; Head to Sluggers for some brews and a game of ski ball

Best Chicago Deep Dish:

Pequod’s Pizza (There’s only one & it’s worth the wait)
Lou Malnati’s (Make sure to get the signature Malnati’s salad with your pizza)

Best Chicago Hot Dogs: 

The Wiener’s Circle (Beware, it’s notorious for treating customers to a Chicago-style dog and some major profanity)

Best Brunch: 

3 Arts Club Cafe (Tip: Arrive early; No reservations, but it’s a furniture so there’s comfy couches every where to plop down on with a cappuccino and relax while you wait for a table)
White Oak Tavern
Batter & Berries 

Best Lunch:

Santa Monica Summer House
Publican Quality Meats
Revival Food Hall
Big Star

Best Snacks:

Garrett Popcorn
Stan’s Donuts

Best Rooftop Bars:


Where to go Out at Night:

The Vig
Untitled Supper Club
Booze Box
The Original Mother’s 

If you try any of my suggestions next time you’re in Chicago, I’d love to hear what you think! Feel free to comment below. In the meantime, if you’d like to see how we managed to squeeze most of the above into a 3-day stay, you can view our full itinerary here.



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