What to Do in Chicago: A Local’s Guide to the Best Food, Drinks, and Must-See Spots
Meet Jen: Your Insider to the Best of Chicago
Jen is a lifelong Chicago resident, creator, and foodie!
Chicago is one of the most exciting cities in the world—full of incredible food, iconic attractions, and neighborhoods packed with character. But planning a trip here (or even figuring out something new to do as a local) can get overwhelming fast.
That’s where Jen comes in.
A Chicago native with a deep love for her city, Jen has spent years eating, drinking, and exploring every corner of Chicago. Whether someone is visiting for the first time or just looking for fresh ideas, she helps people skip the endless research and experience Chicago like a true local.
Instead of wasting hours scrolling through “Best of Chicago” lists or wondering which places are actually worth the time, Jen does the work for them. For just $10, she creates a custom guide tailored to each person’s vibe—helping them eat, drink, and explore with confidence.
For anyone wondering “What to do in Chicago?” or “Where to eat in Chicago?”—Jen has the answers.
Get a personalized guide from Jen - No two guides are the same. they are all built one by one to make sure they match you!
Why Chicago Is a Food Lover’s Dream
Deep dish is a known Chicago staple - but who has the best? Jen Knows
Chicago is famous for its food, and for good reason. Most people know about deep-dish pizza and Chicago-style hot dogs, but there’s so much more to explore. The food scene is diverse, dynamic, and full of incredible spots that many visitors overlook.
Where to Eat in Chicago (Without the Guesswork)
Instead of getting stuck at overhyped tourist spots, Jen helps people find authentic, can’t-miss places that locals actually love. Some of her go-to recommendations include:
The Best Deep Dish for You – Not all deep-dish pizza is the same, and Jen helps people find the one that best fits their taste.
Chicago’s Iconic Eats – From Chicago-style hot dogs to Italian beef sandwiches, she makes sure visitors try the best versions of the city’s legendary dishes.
Brunch Worth Waking Up For – Whether it’s a cozy café or a lively brunch spot, she shares the best places to start the day right.
Perfect Date-Night & Group Dinner Spots – Looking for an intimate dinner or a fun group spot? Jen tailors recommendations based on what someone is looking for.
Instead of sifting through endless reviews, she handpicks the best places based on personal preferences.
What to Do in Chicago (Beyond the Obvious Tourist Spots)
Everyone has a different vibe for what they want to do - Jen has something for everyone
Chicago is packed with incredible things to do, but it’s easy to get lost in the sea of options. Jen helps people find the must-see spots that match their style—whether they want to explore, relax, or experience something unique.
Must-Do Activities in Chicago
Here are just a few types of places Jen can recommend in a custom guide:
Chicago’s Can’t-Miss Landmarks – The city is full of incredible architecture, museums, and must-see sights, and Jen helps visitors prioritize the best ones.
Neighborhoods Worth Exploring – Each Chicago neighborhood has its own personality, and Jen points people to the best areas to visit based on their interests.
Shopping Beyond the Big Chains – From stylish boutiques to unique specialty stores, she shares the best places to shop for something different.
No matter what kind of trip someone is planning, Jen makes sure they get the most out of their time in Chicago.
Why Jen’s Personalized Chicago Guide Is the Best $10 You’ll Spend
Planning a trip is exhausting—there are hundreds of restaurants, bars, and things to do in Chicago, and figuring out which ones are actually worth it takes time.
Instead of wasting hours reading reviews and hoping for the best, Jen makes it easy, stress-free, and fun.
For just $10, here’s what she provides:
✅ A curated list of the best restaurants, bars, shopping, and activities—based on personal preferences.
✅ No research stress—she does the work so travelers don’t have to.
✅ No overwhelm—just a handful of perfect picks so there’s no decision fatigue.
✅ Chicago expertise—from a real local who actually knows the city.
✅ Confidence that every spot is a winner.
No massive list to sift through. No second-guessing choices. Just the best of Chicago, picked for each person.
This is just a sample of a guide from Jen - to Sarah who’s on a girls trip looking for deep dish and hidden gems!
Get to Know Jen More!
Jen isn’t just an expert on Chicago—she’s someone who loves sharing the best experiences with others and making travel effortless and fun.
Want to see more of her adventures, favorite spots, and Chicago insights? Follow her on social media:
📍 TikTok
📍 Youtube
Stay connected for even more local tips, insider recommendations, and behind-the-scenes looks at the best of Chicago!
