This was our first time in Chicago, and we were determined to make the most of it. We crafted this 5 day Chicago itinerary for foodies to dive headfirst into the city’s incredible food scene while still hitting the iconic sights. Known for its jaw-dropping architecture and legendary deep-dish pizza, the Windy City did not disappoint. Here’s a look at our adventure, filled with the tips and must-eats that made our trip unforgettable.
Where We Stayed: Riu Plaza Hotel
We checked into the Riu Plaza Hotel, which had just opened when we arrived. The rooms were modern and stylish, but there were a few teething problems you’d expect from a brand-new hotel. On our first night, the staff was happy to bring us water, but the next day, we were told this service wasn’t available at all—a minor service inconsistency.
The absolute highlight was the rooftop terrace. It offered stunning, panoramic views of the skyline and was the perfect spot to enjoy a cocktail and soak in the city’s energy. While the busy breakfast was standard, the hotel’s prime location made it an excellent base for our explorations, easily justifying the rating. Being able to walk to so many central sights was a huge plus.
Overall ★★★½☆ (3.5/5)
Must-Do Chicago Experiences
River Architecture Tour
You’ll find this in every Chicago guide for a reason—it’s simply the best way to see the city. Cruising down the Chicago River while a guide points out architectural marvels like the neo-Gothic Tribune Tower and the corn-cob-shaped Marina City towers is a truly captivating experience. You gain a deep appreciation for the history and design that make Chicago’s skyline one of the most famous in the world. This is an absolute must.
A Day at the Ballpark: Wrigley Field
We caught a Chicago Cubs game at the legendary Wrigley Field, and the experience was pure Americana. Opened in 1914, it’s one of the oldest ballparks in the nation, and you can feel the history. From its iconic ivy-covered outfield walls to the manual scoreboard, it’s a trip back in time. The atmosphere was electric. We grabbed a classic hot dog and a helmet-shaped ice cream cup. We booked seats in the upper ranks, which offered a fantastic view and were great value.
The Classic City Walk: Parks, Piers & The Bean
For a great look at the skyline, head to the pier at North Avenue Beach. From there, enjoy a scenic walk through Lincoln Park down to Millennium Park. Here you’ll find the famous Cloud Gate, affectionately known as “The Bean.” Designed by artist Anish Kapoor, its seamless, reflective surface distorts the city skyline in fascinating ways, making it an irresistible photo op.
Continue your stroll to the magnificent Buckingham Memorial Fountain, one of the largest fountains in the world. It’s another perfect spot for photos, with the grand fountain in the foreground and the city skyline rising behind it.
Museum Hopping
- Field Museum: An impressive natural history museum where you can come face-to-face with “SUE,” the world’s largest and most complete T. Rex skeleton. The exhibits on ancient Egypt and Native American history are also fantastic.
- Griffin Museum of Science and Industry: As a tech fan, I loved this museum. We caught a special 007 exhibition, but the permanent exhibits, like the U-505 submarine, are incredible. While you’re there, take a walk around the beautiful University of Chicago campus.
- Sears (Willis) Tower: For a bird’s-eye view, head up the Willis Tower. If you’re brave enough, step onto The Ledge—glass boxes that extend from the 103rd floor, allowing you to look straight down 412 meters (1353 feet) to the street below.
A Note on the City Pass: We’re usually skeptical, but in Chicago, it was a fantastic deal. We planned which sights we wanted to see first, did the math, and found that the pass saved us money. It also let us skip the long queues at places like the Willis Tower, which was a huge time-saver.
Logan Square Farmers Market
If you want to escape the downtown buzz and experience a more local, suburban vibe, head to Logan Square. We visited during the farmers market, and it was a delight. It’s not huge, but it’s packed with charming stalls selling everything from fresh coffee and local honey to artisanal cheeses and baked goods.
Chicago Eats: A Deep Dive into the City’s Best Flavors
The food in Chicago is a journey in itself. Here are the spots from our 5 day Chicago itinerary for foodies that we’re still dreaming about.
Breakfast & Coffee
- Ralph’s Coffee: A perfect, stylish stop for a robust cup of coffee. Located inside the Ralph Lauren store on Michigan Avenue, it’s a little oasis of classic American elegance. You can combine it with a browse through the store for the full brand experience.
- Magnolia Bakery: It’s hardly a secret, thanks in part to its fame from Sex and the City, but you can’t leave Chicago without trying their famous banana pudding. It’s a heavenly mix of vanilla wafers, fresh bananas, and creamy vanilla pudding. It absolutely lives up to the hype.
- Nutella Store: A fun, quirky spot we stumbled upon on Michigan Avenue. It’s a novelty cafe dedicated entirely to the chocolate-hazelnut spread, with Nutella-filled crepes, gelato, and coffee. More for the experience than a gourmet meal, but a fun stop nonetheless.
Best Bagels: Tilly Bagel Shop
We’re always on the hunt for great bagels, a quest we take seriously on our travels. Tilly Bagel Shop in the South Loop was a fantastic find. They serve up hand-rolled, boiled, and baked bagels that have the perfect chew. We grabbed an everything bagel with scallion cream cheese and a sesame with lox on our way to the Museum Campus, and it was the perfect fuel for a day of exploring.
Lunch & Dinner: The Heavy Hitters
Au Cheval: This isn’t just a diner; it’s a pilgrimage site for burger lovers. The dimly lit, hip atmosphere sets the stage for what is, without exaggeration, one of the best burgers we’ve ever had. We ordered the double cheeseburger, which comes with three patties (a single has two), sharp American cheese, dijonnaise, and pickles, and we added the thick-cut peppered bacon. Be prepared to wait—we waited two hours, which we used to explore the West Loop. The reward is a perfectly seared, incredibly juicy burger that is worth every single minute of the wait.
Pizza and Oven Grinder Co.: My favorite meal in Chicago, hands down. Tucked away in a historic brownstone in Lincoln Park, this cash-only spot is famous for one thing: the Pizza Pot Pie. They build the pizza upside down in a ceramic bowl—piled with cheese, homemade sausage, and mushrooms—cover it with dough, and bake it. The server flips it at your table, revealing a glorious, gooey, and utterly delicious creation. It’s pure, unforgettable comfort food. 10/10, would go back in a heartbeat.
RL Restaurant: The restaurant counterpart to the coffee shop is just as stylish. We sat at the bar, enjoying fantastic cocktails and a delicious dinner in the sophisticated, buzzy atmosphere. The food and cocktails were both amazing.
Labriola Ristorante: You can’t visit Chicago without trying its most famous culinary invention, the deep-dish pizza. We went to Labriola for our taste of this beast. The crust is thick and high, creating a deep bowl that’s filled with layers of cheese (on the bottom!), toppings, and a rich, chunky tomato sauce on top. It’s less like a pizza and more like a savory pie. One slice is often enough to fill you up!
Velvet Taco: We stumbled upon this vibrant, modern taco joint and were blown away by the creativity. This isn’t your standard taco stand. Their globally-inspired menu features combinations like the Spicy Tikka Chicken, Korean Fried Rice, and the Fish n’ Chips taco. It was a delicious and unexpected find.
The Chicago-Style Hot Dog:
Finally, you must try a classic Chicago-style hot dog from a local stand. It’s a specific culinary creation: an all-beef frankfurter on a poppy seed bun, “dragged through the garden” with seven specific toppings: yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices, pickled sport peppers, and a dash of celery salt. And whatever you do, don’t ask for ketchup!
Final Thoughts on Our Chicago Trip
Chicago completely won us over. It’s a city that effortlessly blends grand, historic architecture with a down-to-earth, friendly vibe. The food scene is world-class, the museums are captivating, and the energy is infectious. Five days felt like the perfect amount of time to get a real taste of the city, leaving us with plenty of reasons to plan a return trip to explore even more of its amazing neighborhoods and restaurants.
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