Chicago | take twelve

Portillo's | Restaurant

A great place to have a Chicago-style hot dog, or a Chicago dog. On a poppy seed bun with yellow mustard, chopped white onions, sweet pickle relish, tomato slices, a dill pickle, peppers and celery salt. The Chicago dog does not have ketchup on it! And they are oh so good. They also have delicious Italian beef sandwiches, chicken sandwiches and super thick milkshakes. Portillo's has locations all over Chicagoland and many are paired with Barnelli's Pasta Bowl. They offer Italian homestyle cooking with many pasta options and really good salad combinations. And the chocolate cake is not to be missed. It is incredibly rich and delicious. With the two paired together there are many options for diners. Each location has a different design theme based on a decade. Watching the employees expedite orders is an impressive process involving them writing your order on a paper bag and saying your order over a microphone where somehow the line cooks hear the orders and make your food. At the far end of the counter someone else gathers your order based on the paper bag with your order, usually in chicken scratch, written on it. It really is something impressive to watch. Their drive through is also expedited differently when it becomes really busy and employees can be found outside taking orders and calling them in; and other employees collecting money and then running orders out to cars. It allows more cars to get through the drive through and not have one order hold up the cars behind them.

INFO | Portillo's

Portillo's Chicago Dog | Photo courtesy Jeff Eats Chicago

Chicago | take eleven

Gino’s East v Lou Malnati's | Pizza Restaurant

Okay, there is much debate about deep dish pizza in Chicago. Which is the best? Which is the original? Which layer is the cheese on? Where should I eat?

The two that I have found to be the best tasting and most authentic are Gino's East and Lou Malnati's. Both offer many locations in Chicago and the surrounding suburbs, plus both offer the option to ship nationwide. Deep dish pizza is unique in that it places the ingredients backwards than a typical thin crust pizza, ending with sauce on top.

Gino's East was founded by two taxi drivers and a friend who were frustrated with Chicago rush hour traffic. They decided to open a pizzeria off of Michigan Avenue and Superior Street. The recipe is the same as when the pizzeria opened in 1966 and it became a legendary place with locals and tourists alike. From the secret recipe for the crust to the vine ripened tomatoes the pizza is always delicious. Many locations are covered in customer's graffiti on the walls drawn with Sharpies. Some even allow you to continue to write on the walls and add to its history.

Lou Malnati, the founder of the namesake restaurant, worked in the first Chicago deep dish pizza restaurant, which is where he learned the secrets of this delicious food. He then took his knowledge and opened his own pizzeria in 1971. Since then 32 locations have opened creating all pizzas by hand using only the finest ingredients. Lou Malnati's places mozzarella directly on the dough, which has been rolled out by hand and placed up the sides of the pan. Then additional ingredients are added, finishing with sauce and a sprinkling of cheese and spices. Their sauce uses only the finest tomatoes and they meet with the growers each year to select the tomatoes to be used in the sauce.

Both are going to provide great deep dish pizza experiences and are worth the 45 minute wait for them to prepare and cook your pizza.

INFO | Gino's East
INFO | Lou Malnati's

Gino's East Deep Dish Pizza

Lou Malnati's Deep Dish Pizza

Chicago | take ten

Museum Campus | Field Museum, Shedd Aquarium, Adler Planetarium, Soldier Field

If you’re up for visting museums in Chicago, then this is a one stop spot for that! All are different depending on what interests you, and the Aquarium is my favorite. There can be quite a line for it however when school is out of session, so plan ahead and buy tickets online. Also check for free days during the week if you aren't restricted to seeing it on a weekend. I have never used CityPass or any similar option in Chicago, but if it gets you ahead of the line and you plan to see enough to make the cost worth it, then I suggest it. The Field Museum has exhibits from Sue the dinosaur to the Ancient Americas to the Mammals of Africa with plenty of things for kids to do. The Adler Planetarium is great for anyone interested in space and space exploration. Soldier Field, home of the Chicago Bears, also hosts other sports and music events. Their website has upcoming shows with information on purchasing tickets. If you love football a Bears game in traditional "Bears weather" is great fun, if you can handle the cold that is! If the weather is nice, Museum Campus can be reached on foot from the Millennium Park area by walking along the path by the water. There are many points where Lake Shore Drive can be crossed safely aside from the winding bridge from Millennium Park, its a busy, fast, wide road in the city so don't try crossing anywhere else.

INFO | Field Museum
INFO | Shedd Aquarium
INFO | Adler Planetarium
INFO | Soldier Field

Chicago | take nine

Millennium Park

Across Monroe Street from the Art Institute, this park is one of my favorite places to visit. Home to the Bean [technically named the Cloud Gate], the Jay Pritzker Pavilion and Lurie Garden spaces. In the winter you can ice skate in front of the Park Grill Restaurant and in the summer enjoy Crown Fountain which has two face statues that “spit” water at each other while the face pictures change. Along Michigan Avenue south of the park are many restaurant options to grab a quick lunch or coffee.

INFO | Millennium Park

Anish Kapoor, creator of the Cloud Gate

Chicago | take eight

Art Institute of Chicago | Museum

I love going to the Art Institute because it is so expansive with art for everyone's taste. They have many stationary exhibits and alternating ones as well. Check the website for what is currently on display. Many of the traveling exhibits require additional ticket purchase with an entry time, which I believe you can purchase online, highly recommended. I still have not experienced the new modern wing that was designed by Renzo Piano, but have heard its a fantastic way to view the art. The new addition also connects the art museum to Millennium Park across the street with a new pedestrian foot bridge.

INFO | Art Institute of Chicago

Sunday Afternoon on the Island of La Grande Jatte | 1884-1886 | Georges Seurat

Chicago | take seven

Segway Tour | City Adventure

This is something that I do recommend, but understand that its not for everyone. It is a different way to see a lot of major sights in the city, especially if you are visiting for just a short period. There are a four tour options depending on what you might be interested in seeing with the company that I've used. I’ve done the Park Glide tour and had a great tour guide who was funny and knowledgeable at the same time. You spend some time learning how to ride a Segway, its quite easy and everyone on our tour was able to successfully learn, and then go out into the city!

INFO | Segway Experience of Chicago

Chicago | take six

Sears Tower | City Views

I’m sorry the Willis Tower.... A great way to see the gridded city streets of Chicago, especially on a clear day. There is a new glass box that extends from the side of the building allowing you to stand over the street. I have not been up recently to experience this new feature, but I can guess that if you don’t like heights its not for you. If you want similar city views the Hancock Tower, located along Michigan Avenue, has a restaurant at the top to enjoy the city views as well. The Hancock also has cheaper admission than the Willis Tower. It is also convenient to shopping and the restaurants along Michigan Ave.

INFO | Willis Tower
INFO | Hancock Tower

Chicago | take five

Michigan Avenue | Shopping

If you enjoy shopping, or even just window shopping, walking around Michigan Avenue is a unique experience. With its many stores you are sure to find something to help remember your time in Chicago. You can enjoy shopping inside at Water Tower Place, or in one of the many designer shops on the street. Head north from the Chicago River toward the historic water tower and enjoy the photography exhibits inside that are often changing.

INFO | Historic Water Tower

Chicago | take four

Volare | Italian Restaurant

An Italian restaurant that I’ve eaten at plenty of times, always with great service and food. A good wine list, large menu and many daily specials make this a great option. Friends have described it as better than their favorite NYC Little Italy restaurant. Make reservations though, even on weekdays it fills up! There's a reason I've eaten here many times, the food is delicious. My favorite is their gnocchi with vodka sauce and sausage cut up in the sauce. AMAZING!

INFO | Volare

Chicago | take three

Navy Pier | Family Fun

A fun place to walk around for all ages. The Chicago Children’s Museum is located here if you have the kids along. There is also a ferris wheel that provides fantastic views of the city, sometimes with a long wait, and other rides for entertainment. For the adults there is a beer garden and plenty of food options. There are also dinner cruises that leave from Navy Pier and plenty of other entertainment that will be talked about loudly, trying to get you to cave in and participate of course.

INFO | Navy Pier + Children's Museum

Chicago | take two

Fox & Obel Food Market | Lunch spot

This grocery store is in the same building block as the Chicago Line Cruises and also offers amazing lunch options [sandwiches/soups/cookies] or coffee and dessert for an afternoon pick me up. I love their sandwich creations and this is very convenient when going on one of the boat tours! Eat inside at their tables or take your food to go and enjoy eating on one of the benches behind the building overlooking the water where the boat tours leave from.

INFO | Fox & Obel

Chicago | take one

Chicago Line Cruises | Architecture Boat Tour

Located in the River East Arts Center, walk between the building and pier to find the ticket office. Buy tickets online ahead of time for tours in the summer, they will sell out. The last tour is considered a booze cruise, it goes through the locks and onto Lake Michigan after going up the Chicago River. It will not go down the branches of the Chicago River, but I enjoy it more because you get to experience the locks and be on Lake Michigan.

INFO | Chicago Architecture Cruise