Curator’s statement
My first experiences in Chicago were spent wandering the streets with my best friend on quick weekend trips, leaving the city with a special place in my heart. Chicago has a way of offering something for everyone, especially when it comes to spending quality time with friends. This girls’ weekend itinerary is designed around good food, great company, and a relaxed approach to exploring the city.
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Day 1: Arrive & Millennium Park
Arrive at ORD or MDW (ORD is better for city access). After dropping your bags at the hotel, head to Millennium Park for a stroll to see Cloud Gate (the bean) and the rest of the beautiful park space. On the far end of the park is The Art Institute of Chicago. Stroll through the museum to see some really beautiful and famous pieces. Take a quick walk across the river for deep-dish pizza at Giordano's (100x better than Lou Malnati’s). Finish the night at RedHead Piano Bar for an intimate, casual drink.
Day 2: See the city
Start your day with a Chicago History & Architecture Boat Tour. I know this sounds touristy—and it is—but for good reason. Chicago by boat gives you a new perspective of the city. Taking this tour myself, I learned many things about not only Chicago’s skyline but architecture trends in general that can be spotted in other cities like NYC. I recommend arriving a few minutes early so you can secure a spot in the upper deck.
After the boat tour, head to River North for lunch at The Smith. Next, either go to the Magnificent Mile for big-box shopping, or head to Wicker Park for some great thrift shopping. In the evening, go out for dinner in the West Loop (High Five Ramen, Sushi Dokku, Time Out Market). After, grab some drinks and feel like a local at these spots—Lazy Bird, Goodnight John Boy, Bodega Taqueria y Tequila (speakeasy), and Reading Room.
Day 3: Slow day in the city
Today’s all about relaxing with the girls. Either start your day at the spa (St. Regis Chicago or Nobu Chicago), or take a yoga class at the top of 360 Chicago for a unique wellness experience. After some restorative time, shop around the West Loop and finish the day with an elevated dinner experience (Beatrix, Girl & The Goat, Alla Vita, Sepia).
Day 4: Depart from Chicago
Enjoy brunch at The Hampton Social—River North or The Dearborn, depending on your departure time and hotel location. Enjoy a final walk along the river if you have the time.
Need to know
West Loop is my favorite neighborhood in Chicago—it feels more local than other areas like River North and a bit quieter because of that, even though it gets lively at night. Some honorable mentions are the Griffin Museum of Science & Industry, Lincoln Park Zoo & Conservatory, and the Cubs Stadium. If you can’t make it to a game, a tour of the stadium is great—they allow you to walk out on the field and you learn a lot of history during the tour. Reservations are required at the Lincoln Park Conservatory, but are not difficult to get. The Rookery Building is a stunning piece of Chicago’s history and architecture, with tours available here as well.
And finally, if you’re going to Chicago, you need a Chicago-style hot dog. I highly recommend Portillo’s in River North. Everything on the hot dog—never ketchup.
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