When people think about foodie vacations or shopping getaways, cities like New York, Paris, and Los Angeles usually steal the spotlight. But after spending time in all of them, I honestly think Chicago is one of the most underrated destinations for both.
What I love most is that Chicago gives you so much of what those cities offer—amazing restaurants, incredible shopping, beautiful architecture, and vibrant neighborhoods—but without feeling quite as overwhelming. You can spend the morning over a fabulous brunch, afternoon shopping while absorbing the sites, followed by dinner at a Michelin starred restaurant. The city checks all the boxes for an amazing day!
The Food Scene Lives Up to the Hype
Chicago has a reputation for great food, and it absolutely deserves it.
Sure, everyone talks about the deep-dish pizza (and yes, you should try it), but that’s only scratching the surface. Some of my favorite meals in the city have been completely unexpected—from incredible tacos and handmade pasta to authentic Vietnamese pho and some of the best steakhouses in the country.
If it’s your first visit, don’t leave without trying:
- Deep-dish pizza: Lou Malnati’s and Giordano’s are the staples
- Chicago-style hot dogs: The best are at the ballpark, if you can catch a game—go for it!
- Italian beef sandwiches
- Garrett Popcorn: There’s a freestanding shop on Michigan and bonus, there’s a kiosk at O’Hare airport in case you forget to grab while out and about
- A classic Chicago steakhouse: All the names, Gibson’s, Morton’s, Palm, Smith and McCormick’s and hidden gems like Bavette top the list
The best part? You don’t have to spend a fortune to eat well here. Some of the city’s most memorable meals come from neighborhood restaurants that locals have loved for years.
Every Neighborhood Has Its Own Flavor
One of my favorite things about Chicago is how different each neighborhood feels.
You can wander through Chinatown for authentic dumplings, head to Little Italy for fresh pasta, explore Pilsen for incredible Mexican food, or spend an afternoon discovering restaurants in the West Loop, one of the city’s hottest dining destinations. Fulton Market in the West Loop has some really good options, as well as the restaurants along Randolph. I personally love Au Coeval’s simple, yet appetizing menu!
It’s the kind of place where every meal can feel like you’re visiting a different part of the world.
Fine Dining Without the New York Prices
If you’re celebrating something special, Chicago is one of the best cities in the country for fine dining.
The city is home to numerous Michelin-recognized restaurants and award-winning chefs, but compared to cities like New York, it’s often easier to get reservations—and in many cases, you’ll spend less for an equally memorable experience.
Shopping Is Just as Good as the Food
Once you’ve eaten your way through the city, it’s time to shop.
Most visitors start on the Magnificent Mile, and for good reason. It’s filled with luxury brands, department stores, flagship retailers, and plenty of places to stop for coffee or lunch between shopping bags.
But some of my favorite finds have actually come from Chicago’s neighborhoods.
Wicker Park is perfect if you love trendy boutiques and vintage stores. Andersonville has charming independent shops that are ideal for finding unique gifts, while Lincoln Park offers a mix of local boutiques and familiar favorites.
These are the places where you’ll discover something you won’t find back home.
Bring an Extra Suitcase
One thing I never expect when I visit Chicago is how much food I end up bringing home.
From artisan chocolates and locally roasted coffee to gourmet popcorn, specialty bakeries, and incredible food halls, there are so many edible souvenirs worth packing.
It’s almost impossible to leave empty-handed.
One of the Best Big-City Values
Chicago also offers something that’s becoming harder to find in major cities: value.
Hotels are often more affordable than New York, restaurant prices tend to be more reasonable, and getting around is surprisingly easy thanks to the city’s excellent public transportation.
That means you can spend more of your budget on memorable meals, unique shopping, and experiences instead of transportation and overpriced accommodations.
My Ideal Chicago Day
If I had just one day in Chicago, it would probably look something like this:
I’d start with breakfast at a neighborhood café, spend the morning shopping along the Magnificent Mile, wander through Wicker Park looking for local boutiques, grab an Italian beef for lunch, visit one of the city’s incredible museums, and finish the evening with dinner overlooking the skyline.
It’s the kind of city where every day feels full without feeling rushed.
Final Thoughts
Chicago has quietly become one of my favorite destinations for both food and shopping. It offers everything you’d expect from a world-class city—award-winning restaurants, luxury shopping, diverse neighborhoods, and unforgettable experiences—but often at a better value than many of its competitors.
Whether you’re planning a girls’ getaway, a romantic weekend, or simply looking for your next city escape, Chicago deserves a spot on your travel list. Come hungry, wear comfortable shoes, and leave a little extra room in your suitcase—you’ll probably need it.
