Chicago is perhaps one of the major U.S. cities I know best. Growing up in Wisconsin and then relocating back to the Midwest after college, I have spent many days visiting and driving through this great town. More recently I have spent time here on business often which has given me some insight into the hotel scene as well. This city is near and dear to my heart, and ultimately a city I can see myself eventually ending up in. 

EXPERIENCE

Chicago has so much to offer to visitors, especially in the warmer months. Be sure to visit Millennium Park for a free concert and to check out the Cloud Gate sculpture, better known as the Bean. The park also has lovely gardens and is very close to the Art Institute of Chicago. This is a great walk to combine with a shopping trip down the Magnificent Mile. This walk will boast views of the Chicago River and open up to sights of Lake Michigan. Be sure to check out the marina and Chicago’s many beaches if you plan to visit in the warmer months.

Bikes and the El are great ways to get around the city and visit some of Chicago’s more outlying neighborhoods such as Wicker Park, Lincoln Park, Logan Square or Ukrainian Village. All of these neighborhoods have a ton of character and are home to lots of fun and eclectic shops and restaurants. 

There are so many things to see while in Chicago, but favorites of mine have included the Shedd Aquarium, Navy Pier, Museum of Science and Industry, Lincoln Park Zoo, Adler Planetarium, and Wrigley Field. Chicago is also home to lots of entertainment venues, so be sure to catch a show in one of Chicago’s many historic theaters while in town. 

STAY

In the past few years I have had the chance to stay in many of Chicago’s downtown hotels. I a have also recently had two wonderful experiences staying in Airbnb houses in Logan Square and the Ukrainian village, be sure to check this out as an option if you are looking for a more unique experience and to get off the beaten path of the Loop.

Favorite hotels have been the W Lakeshore, great for beach access. The Hotel Sax, Silversmith, Hotel Allegro, Hotel Felix, and Palmer House have also been nice. Noteworthy nice stays have been at the Swissotel and  Sofitel, which is perhaps my favorite downtown hotel. It is classy and cozy and nestled in a quiet pocket off of the Magnificent Mile. The Wit is nice too and offers a great roof deck for the evenings, with a beautiful view of the lake and downtown. In a recent trip I stayed at the new Thompson Hotel, which really impressed! I loved the decor, very hipster friendly, complete with a great new eatery attached, Nico Osteria.

EAT

While downtown, be sure to have breakfast at Rick Bayless’ XOCO. Pastoral, Japonais, Frontera, The Purple Pig, Slurping Turtle, Gilt, and GT Oyster Bar are some of my favorites while in the Loop. I seem to find myself eating lots of pork while in Chicago, namely pork belly. Publican and it’s sister butcher shop, P.Q.M. are great stops if you’re looking for such things. The best coffee in Chicago is Intelligentsia, it’s worth the wait!

Other favorites include Avec, Cafe BabaReeba (tapas brunch), the Bedford, and Cafe Au Cheval (best bloody mary ever). Former top chef Stephanie Izzard has a great spot called Girl and the Goat. If you visit here be sure to try the octopus dish, it is my vorite thing on the menu. She has a new restaurant across the street called Little Goat that is wonderful for breakfast and even has a rooftop deck. 

The outlying neighborhoods have lots of great dining spots as well. While in Wicker Park, don’t miss Big Star for tacos or Piece for a clam pizza. Revolution Brewery is also a good spot for a beer and casual meal. Hit Logan Square for drinks at the Whistler, dinner or brunch at Longman & Eagle and a meal at Telegraph. Another good stop outside the city is Urban Belly, home to some wonderful soups and noodle bowls, the owners have another spot in Wicker Park called Belly Shack, which I have not yet checked out. Oh, and if you’re in town for a cold day, Hot Chocolate near Wicker Park makes the most rich, delicious cup of Mexican cocoa I’ve ever had. Other new favorites include Parachute, Beverly Kim’s new Korean place in Avondale and Nico Osteria in the Loop. 

Chicago is also home to several spots I have not yet tried, but desperately wish to. Those include Alinea, one of the country’s top gastronomical experiences. Also it’s subscription based sister restaurant, also prix fixe menu, NEXT. I have also yet to try Topolobambo, Blackbird or Yosho, which I’d love to visit.