As I had mentioned in other blog posts, I used to live in major cities for months at a time for work. Chicago was one of them. And while living there, the one thing I did regret the most was not doing as much as I should have on the List. If I was smart enough, I could have completed everything that Chicago had to offer. But since I didn't, here are my thoughts on the things I did do.
Art Institute of Chicago - This building is located near Millennium Park and close to city center. I thought it was a decent museum to go to, and the admission price of $18 wasn't too bad for what it had to offer. If you only have an hour to spare, the pamphlet provides you with a recommended path to follow to see the major artwork that sums up the museum. Do I recommend it? I would, only if you have the time and money to spare. I consider this place of interest to be optional. Also, in somewhat nearby distance (about 7 blocks) is the famous Willis Tower (formerly known as Sears Tower) that has the Skydeck glass encasement overlooking the city. It's touristy but fun to check out! For those that love panoramic city views, another place to see the entire city is the John Hancock Center.
Millennium Park - Since the Art Institute of Chicago is located right next to it, it seems only natural to talk about this awesome park. This park will always be a tourist zone due to the world famous Cloud Gate (you know, the metallic bean shaped sculpture). But keep exploring around and you'll discover other awesome art installations, like the Crown Fountain (which displays videos and spits out water). One of the must-do things locals do in the summer is attend one of the many concerts at the park, called the Millennium & Grant Park Music Festivals. Here's the thing though; when I went to see Idina Menzel perform at the park the tickets were cheap, you can bring food/drinks in and have a picnic on the back lawn, but you could barely see her. So if you want to enjoy listening to her and spend time with your friends while doing it, then you should definitely attend. But if you are expecting a more traditional outdoor concert venue, then be prepared to buy the more expensive tickets up where the actual seating is. Another festival they hold at the park is the Taste of Chicago. The city hypes it up to be this grand food festival, but in reality, it's kind of lame. There aren't that many food vendor booths to begin with, there aren't that many well known restaurants on display, and the food quality is about the same as carnival food/food trucks. However, it's free to attend so it won't hurt to check it out. I just wouldn't recommend flying out solely to visit this festival.
Chicago Architecture Tour - There are a few boat tours in Chicago, but the List recommends taking the one Chicago Architecture Foundation offers. Whenever I'm in a new city, I usually like to fly my parents out to visit me because it's nice to see family and I enjoy seeing them explore new places. And since this boat tour was quintessential in exploring Chicago, I took them on it. Now if it ends up being a cool day when you're in Chicago, I'd recommend bringing a jacket for this tour. You might not think it's cold, but once you're out on the lake and the wind starts blowing, you will be. It was a pretty amazing tour, especially at the end when they take you out onto the lake and you can see the famous Chicago buildings all lined up in a row. I must admit that some of the information given on the tour was a bit boring, but overall it's a great way to see the city.
Frank Lloyd Wright Home & Studio - If you are a fan of Frank Lloyd Wright's architectural design, then you should definitely come visit his home and studio. It's out of the way from Chicago's city center, so if you don't have a car, it's gonna be an expensive Uber ride over. I'm not that big of a fan of architecture, but I do appreciate great design when I see it. So when I booked the guided tour, I was a bit worried that I wouldn't enjoy it. But I absolutely did. I didn't know much about the designer, so it was eye-opening to hear everything about this man and his design philosophy. The tour includes a visit inside and outside the house, and you'll agree the house interior is really beautiful and designed with purpose.
Magnificent Mile - If you didn't know, I love shopping. I'm always excited to see any shopping related items on the List, cause it gives me even more of an excuse to do so! You can really spend the entire weekend on this strip of shops, hotels, and restaurants. The book does mention this strip but doesn't really mention where to go while you're walking it, so think of this area as Chicago's answer to New York's Fifth Avenue. I'd recommend eating at the RL (Ralph Lauren) Restaurant where Oprah famously admits to loving their fries or M Burger (Chicago's version of Shake Shack). But really, you come to Mag Mile for the shopping.
Second City - For a nighttime activity, consider going to see the comedy troupe at Second City. This place is very well known in the comedy world since Tina Fey, Amy Poehler, Dan Akroyd, and Chris Farley were all graduates there. If you've been to a comedy club, this one isn't all that different. I think the only difference I saw was the seating arrangements being all horizontally long instead of having those individual round tables. I had a fun time there, and you probably will too.
Deep Dish Pizza - The List recommends Pizzeria Uno or Pizzeria Due (which I haven't gone to yet). But even though Pizzeria Uno has historical significance as being the originator of deep dish pizza, I just thought it was OK. The other options I tried were Giordano's (very touristy and offers behind the scenes tours of pizza making), Gino's (good, but not memorable), and ultimately the best deep dish pizza I had in Chicago, Lou Malnati's. It could be their buttery crust from a secret family recipe, or it could be the exclusive sausage blend they have. Either way, it is hands down the best deep dish pizza I had in Chicago.
Restaurants I Ate At - From all the restaurants I went to in Chicago, the one restaurant that would top my list is The Girl and the Goat. The place is always getting booked up, so try to make reservations well in advance. If they end up being booked full when you get there, try Au Cheval across the street. They have awesome burgers. For something much more pricier, try getting reservations to Alinea. Every time I looked for reservations, there were only early and late dinner time slots open. But when you do get one, it's a pretty amazing feeling since they're hard to come by to begin with. Dinner at Alinea has been highly praised by the food Gods and I kind of understand why. I had the 16 course prix fixe dinner, running around $285/pp depending on the time of day you have your reservations for. The presentation was on point, most of the dishes tasted great (except the pork belly covered in seaweed that looked like coal and the "cement"), and it felt like dinner theater. I felt they sacrificed the taste of the food in some of the dishes in order to make it more artistically presentable. Another pricier joint I ate at was dinner at Topolobampo, known to locals as just Topolo. When I was there, you were able to partake in the coursed menu or purchase a la carte. Since I wasn't that hungry when I went, I did the a la carte menu. I forgot what I ordered that night so I can't really give you any recommendations. The place is also pretty small since it shares the restaurant space with Frontera Grill, the middle sister to Rick Bayless' restaurant collection in Chicago. Frontera Grill is less stuffy and much more relaxed of the two. Like Topolo, I don't remember what I got here except the Carne Asada which I remember being really good. For cheap quick eats, I'd recommend Al's No. 1 Italian Beef. It's like having a roast beef dip, but with a Chicagoan twist. Portillo's (near Mag Mile) is also a great option that I recommend! Get their hot dog, beef sandwich, or chocolate cake! Hot Doug's, a hot dog joint, has closed down so no point in trekking over there. And the cheeseburgers at the famous Billy Goat Tavern aren't really good, so feel free to pass on this one too.
Wrigley Field - The Wrigley Field is a cute baseball stadium you should at least visit from the exterior if you can't catch a game. On a hot day, try to avoid the bleacher seats by the score board. I was burnt to a crisp from being out in the sun for that long! But for picture taking, it's a great place to be sitting since you get to see into the ball pit. I've been to a few baseball games in my lifetime and the experience here takes the cake....for now.
Sadly, it will probably take me 3-4 more trips to finish out the List for Chicago. At least the airfare getting to Chicago is usually pretty cheap! Hope you follow me on my goal to finish it up!