Sisters take Chicago: A three day jaunt through the Windy City

Chicago skyline

Photo: Roman Boed

Chicago, the Windy City; the epicenter of city life in Illinois. Growing up in the Land of Lincoln Chicago was the big city to visit for school trips, fancy prom dresses, and weekend getaways for those that could afford it.

Now, living in Minnesota, it is still a quick trip for a weekend getaway, especially when your travel pals are still located in Illinois. The easy access, affordability, and sense of familiarity is why we chose Chi town for our first annual sisters weekend.

We desired a little relaxation and plenty of space to have fun so we rented a house instead of going the hotel route. I found a great little place on Home Away located near Lincoln Square and if I ever moved to Chicago this is probably where I would end up. (Other than the fact that the house across the street was going for close to a million!)

Easy access to the brown line, a beautiful park, lots of little restaurants and local shops, and plenty of history. Designated Lincoln Square in 1925, the area use to be heavily German. You will still find a few German relics, such as the Chicago Brauhaus, but the neighborhood has become an eclectic mix of smaller chains such as Fleet Feet and unique shops like Merz Apothecary.

Chicago el

Photo: Tony Webster

Day one I found a tasty little place named Gene’s Sausage Shop that would be my go-to spot if I lived there. A great deli, prepared salads, and killer giant pretzels; not to mention, the upper level alcohol selection and rooftop beer and wine garden. Then of course there was the consignment shop, A Secret Closet, where I grabbed a whole new outfit in less than 15 minutes and chatted with the friendly staff.

Once my sisters joined me the next day, we spent a little more time wandering Lincoln Square for shopping and dining. We enjoyed a morning coffee stop at The Grind, which seemed to be the favorite among the locals. The wait in line was well worth it! We walked out with delicious iced coffees and a moist zucchini muffin.

A quick trip on the brown line and a switch to the blue line got us to Wicker Park/Bucktown. This area is now very popular among the younger Chicagoans, and therefore has a reputation as a hipster area. However, it has great shopping, restaurants, and people watching. And it is a nice alternative to the crowds and large national chains that clutter the Magnificent Mile. We wandered up and down the neighborhood and enjoyed a leisurely lunch at Francesco’s Forno. The wide open windows and classic rustic settings made us feel like we were dining al fresco in a café a world away. We made a post lunch pit stop at the Toms store which offers coffee that gives back along side their comfy shoes that give one for one.

Wicker Park

After a long day of walking, our legs were cramping and we were ready to head back to our apartment. We decided to stay close to home base and dine in Lincoln Square. Of course, that didn’t really narrow our options or make it any easier to decide on a restaurant. We finally settled on Barba Yianni Grecian Taverna for Mediterranean and it was a great choice. The staff was friendly and knowledgeable; and the food was fantastic and authentic. We highly recommend the humos, greek salad, lamb kebobs, gyro platter, and olive plate. Really I don’t think you can go wrong with anything on the menu, but be prepared to eat big or share a meal.

Day two we hopped back on the brown line and jumped to the red line to go check out Navy Pier. Unfortunately, Navy Pier is undergoing a massive redevelopment and is currently missing some of the grandeur and fun that it is known for. I’m sure it will look amazing when it is finished, but for now I’ll keep it off the list of possible stops for future trips.

River North

Although Navy Pier was a bust, we really enjoyed our lunch at Osteria via Stato. So if you find yourself in the River North neighborhood, stop by for great pizza, Italian specialties, and drinks.

Unfortunately, we didn’t have more time to explore further, but I’m sure we will visit again. Good thing, because I’ve already started a list of places I haven’t gotten to visit yet: Chicago Foodseum, the Andersonville neighborhood, Scone City in Wicker Park, River Roast for a Hoosier Mama Pie. Any other things I should add to the list?

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