My second trip to the Windy City was every bit as enchanting as the first. I popped by for a few days to accompany my friend Nisreen on her work trip. She’s a top dog marketer in the food world and was attending the National Restaurant Association’s convention. The last time I went to Chicago it was January, it was like a dream visiting the city in nice weather. It’s a totally different metropolis.
This was Nisreen’s first time in Chicago so we hit all the big sights including Anish Kapoor’s Cloudgate, the Wabash mural corridor, and Navy Pier. Millennium, and the bordering Grant Park, are beautiful, European-style gardens that merit a visit, and if it’s summertime, a picnic. I can’t speak to accommodations in this guide. My first trip to Chicago I stayed with a friend and this time around Nisreen’s work put us up in the Kimpton Gray. Though it was beautiful and well located, I didn’t get a very friendly vibe from the staff.
What to Do
Navy Pier is touristy but I feel like you’ve got to see it once. There are carnival rides, food stands, performances, and restaurants. It’s a long boardwalk that stretches out into Lake Michigan and there are lots of spots to stop with a cocktail and enjoy the view. The Ferris wheel is a nod to the Chicago World’s Fair in 1893. George Washington Gale Ferris Jr. invented the first Ferris wheel as the fair’s central attraction.
For art lovers (or Instagram lovers) the Wabash Arts Corridor is a mile of murals in downtown. Equally as wonderful as the murals is the website which gives wonderful, detailed information and location for each one. The mural below isn’t in the Wabash art walk but it is in the West Loop district which has some of the best food in downtown.
For more structured art, I recommend The Art Institute of Chicago, known for pieces like Nighthawks by Edward Hopper, Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat, and American Gothic by Grant Wood. Per my tastes, I sought out their solid collection of Goya portraits and prints. Most of their prints are off view but they do have out the Friar Pedro and El Maragato series. Chagall’s stained glass triptych is also a must-see.
To cap off the art equation we saw Hamilton at the CIBC Theatre. I’m not sure why Chicago has a separate run of the show but it’s a great way to see the production without paying a trillion dollars in New York. Some members of the original cast performed and everyone was amazing. There isn’t a bad seat in the theatre, we sat in the upper mezzanine for only $100 apiece.
Where to Eat
The Girl and the Goat is one of Chicago’s most well know restaurants but it’s often booked up way in advance and the pricing is quite steep. I recommend Proxi as an awesome alternative. Located in the West Loop, it’s a beautiful, huge, contemporary space. The staff is friendly and there’s a spacious bar as well as ample table seating.
The innovative menu is meant to reflect global cuisine influences. The small plates offerings range from Indonesian Pork Jerky and Coal Roasted Oysters to Kashmiri Lamb Shank and Burrata. Everything is delectable, each dish with a subtle, penetrating mix of flavors. Plan to be at Proxi for a while, you can spend hours savoring each dish.
Drinks and desserts are equally as interesting. I had This Air Is Curious with novo fogo cachaça, carpano bianco, rhine hall mango, yellow chartreuse, and St. George absinthe. It was a wonderful, unexpected mix of flavors. In each creation you can taste Chef Zimmerman’s creativity and passion. The team’s love for food shines through every piece of the Proxi experience.
For breakfast I recommend you head to the top of the world, or at least the top of Chicago. Willis Tower offers a private breakfast before the attraction opens to the public. You receive a private escort up at 7am, have the space to yourself for as much sightseeing and picture taking as your heart desires, and then dine on a gourmet breakfast overlooking the city. It was a spectacular experience. There’s nothing like watching the sunrise over the city, from above it.
After breakfast you can either stay while they open the Skydeck to the public or get ushered out a back door to avoid the fray. It’s the ultimate VIP way to experience Willis Tower.
These are just a few tips from our whirlwind 48-hours in Chicago. It’s a spectacular city with so much to see (and so much to eat!). I’m already planning for my next visit. Where are your favorite Chicago spots?