Experience what true sightseeing in Chicago is all about by taking in the culture beyond the downtown scene.
A trip to the vibrant neighborhood of Lakeview gives you a taste of hip, authentic Chicago flavor. First, start your journey at a noteworthy lodging experience, then take a walking tour of where to shop, eat, party, and more in the area.
Villa Toscana Guest House
A great way to experience all that Chicago has to offer is by staying in Lakeview at the Villa Toscana Guest House. The Victorian-style bed-and-breakfast was constructed in the late 1800s, and offers eight remodeled European-themed rooms such as British Colonial, neoclassic, and Venetian. Its cozy, secluded vibe is designed so you never want to leave (at least, not until breakfast is served). Shrubbery surrounds the entrance, making you feel like you’re entering a secret garden. Best of all, the prime location provides you with the proper opportunity for awesome sightseeing in Chicago.
After spending some time in your old-timey lodging, you’re ready to experience that same feeling in the surrounding community. You don’t have to be a bookworm to appreciate The Bookworks, a boutique-style shop selling rare, vintage, and out-of-print books. Just a 6-minute walk from where you’re staying, it’s the sort of place you can spend an entire afternoon exploring, as the extensive selection of first editions and used books can definitely keep you occupied. But what makes it even cooler is that it’s more than a bookstore—it appeals to the historian within you with its immense collection of antique photos, rare albums, and vintage papers.
Also within walking distance from Villa Toscana is this sleek craft brewery where hops-centric suds are designed to match your menu selections. The brunch service, called “Kegs & Eggs,” remains a distinct, seasonal offering in the neighborhood. You find that the chilaquiles (made with house-made fried tortillas and pico de gallo) as well as your friend’s country fried steak and eggs paired with “crushed” breakfast tomatoes, which perfectly complement the Belgian-style IPAs and pale ales.
For late-night snacks, you expect the likes of poutine topped with applewood smoked bacon and a vegetable Reuben stuffed with savory grilled portobello mushrooms. The best part of your visit? You found a drink you really love—so you take a growler of it to go enjoy back at your room.
Pastoral Artisan Cheese, Bread & Wine
Also down the street is Pastoral, a cheese and wine-focused venture where guests may purchase items to take home or enjoy on premises. In addition to cheese, breads, and charcuterie options, you notice that the menu features a number of artisan sandwiches and salads. You pick up a souvenir that’s also a picnic option, as Pastoral specializes in gourmet baskets. Your final selection is the “Taste of the Midwest,” stuffed with local cheeses, cured meats, summer sausages, dried Michigan cherries, and spiced almonds. Its local, tasty, and varied culinary goodness is worth bringing along as you partake in sightseeing in Chicago.
For a combination of shopping, education, and caffeine during sightseeing in Chicago, you take a nice stroll to TeaGschwendner, an upscale tea-focused shop. Once inside, you indulge in everything tea. With so many loose-leaf options lining the walls and menu, you find it difficult to pick an option. Thankfully, you sample a few selections to ensure you make the right decision (not that there’s a wrong one here). You finally decide on some earthy matcha green tea, steeped to taste perfection. But it doesn’t stop there—as you immerse yourself in learning about tea traditions, preparations, and culture from the friendly staff.