I really want my son to grow up knowing and loving the town that his Mamma is from. I hope he does, and I can't wait for his first Cubs game. Here are a few of my favorites:
I think Lula Cafe is hands down my favorite spot to grab lunch or brunch. It's in a neighborhood of Chicago called Logan Square which is just West of Lincoln Park where I grew up. The food is always delicious at this place. They make an amazing turkey sandwich with avocado that's delish. The crowd is pretty hip and for some reason I always run into my old Bio teacher Mr. Sherry here and you probably will too if you go. P.S. They also have a fancier restaurant that I've tried twice which is also amazing called Nightwood in the hip Pilsen neighborhood that is really great too.
Another lunch favorite is Jane's in Bucktown. The food is really good here and the space is cute. I had my baby shower here and it was a lot of fun. It is a great spot for a shower because the day we had ours there was another shower going on. There are probably great new spots (this one is definitely been around since the nineties) but I love this place.
People take their hot dogs very seriously in Chicago. My younger brothers literally cried when their favorite hot dog spot in Lincoln Park closed a few years back. I think unless you are a vegetarian you have to indulge while you are in town. People will probably say the place to go is Hot Dougs. I've never actually been because this place opened after I left and whenever I drive by the line is out the door and crazy. You have to be dedicated. Also while this place does a classic Chicago dog (no ketchup, sesame seed bun, etc) they also have some weird ones and they have duck fat fries on the weekend. By all means check this place out and tell me how it is, but if you want a simple, delicious Chicago dog I always head to Murphy's. It's in Lakeview which is the home of Wrigley Field and it's just a simple, classic, delicious hot dog. I always go for the Char dog fyi which they grill.
Who is this dreamy man? Why it's Paul Kahan and every single one of his restaurants in Chicago are delicious and amazing. I am serious that his food rivals anything you've had in New York or Los Angeles or really anywhere for that matter. He owns Blackbird, Avec, Publican, and he recently just opened Publican Quality Meats for all of your butchering needs. Choose any of these places and you won't be disappointed.
If you are in town and the weather is warm, and you are in the mood for a swanky drink than I love NOMI at the Park Hyatt. It's also great for lunch. You waltz right into their lovely lobby and head for the elevator on your right (like you know exactly what you are doing) and head up to their roof top restaurant/bar. You are right on Michigan Avenue and you have a gorgeous view of the city and you can see the original Water Tower Building (one of only two buildings that survived the Chicago Fire). The hotel is also so lovely and swank if you need a place to stay and the rooms aren't too outrageous. Although be warned my cousin and I once stayed here and we literally got a noise complaint for watching "Enchanted." I think this probably says something about the clientele at the hotel (they do not like noise of any kind) and something about us (that we are super cool since we stay at hotels and watch "Enchanted"). This place just gives visitors a sense of the beauty of Chicago and they make a mean drink.
If you are more in the mood for a down and dirty drink with a photo-booth on the side than go to Rainbo in Wicker Park/Ukrainian Village. It's classic Chicago and also had lots of cool kids (assume it still does - sorry if you go and it doesn't). This place has some cheap Chicago beers and can make a mean drink and like I said they have a photo-booth. I have already written about my love of the photo booth. Even if you have a terrible night at least you have some cute, fun photos that will perhaps make you think you had an awesome night a year from now.
The entire Lakefront in Chicago is stunning and worth exploring but I will always be partial to Lincoln Park where we have the Zoo (which is free every day of the year and great) and the Lincoln Park Conservatory pictured left. This place is also free and always open (My family stopped in last year on Christmas day when Hank wasn't even three months yet). It's so lovely here. It also holds a special place in my heart because my old school is just two blocks from here and this is where we would come to time how long it takes you to run the mile (three times around is a mile if you are so inclined). A few years ago I even made my youngest sister time me while I sprinted around the path three times furiously trying to come close to the time I had in sixth grade. I am sad to admit I think I doubled over in pain afterwards and needed my Mom to come pick me up. Perhaps it was the giant coffee I drank before. I am a better runner now I swear. 
The Art Institute of Chicago is an incredible museum. I have a special affinity for this place because my step-grandmother is a docent here. She was recently honored for her fifty plus years of service. She always took us on a tour of every visiting exhibition - John Singer Sargent, Cezanne, Monet, etc. We spent hours exploring the museum. She always challenged me to think about the painting differently and she helped me discover a lifelong love of art history. The permanent collection is incredible as well. There are some big paintings here such as "A Sunday on La Grande Jatte" Seurat's pointillism masterpiece, and Marc Chagall's stain glass windows. Be sure to head downstairs and check out the Thorne Miniature Rooms. They are sixty-eight perfect miniature interiors, each representing a different time period and style (Louis XV Boudoir or a 1940's California living room). Recently they've completed a beautiful modern wing of the museum that I've only scratched the surface of but can't wait to visit again soon.
There is so many more wonderful things to see in Chicago. Just writing this gets me excited for my visit.
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