When I picture Chicago I think of deep dish pizza, Chicago style hot dogs, jazz/blues/house/electronic music, Lake Michigan, city living, tall skyscrapers, unique architecture, Joffrey ballet, Dunkin Donuts, L train, Garrett popcorn, Great Lakes and The Loop. Here’s my favorites:

Skydeck Chicago (Willis Tower) / 360 Degrees Chicago (John Hancock Tower)

Spectacular beautiful views of the city. Go at night to see all the city lights and enjoy the magnificent city scape view of the buildings during the day. My personal favorite was 360 over Skydeck because of the beach views, but both were terrific. Skydeck has the cool photo opportunity with the glass ledge which was a highlight.

Giordano’s & Lou Malnati’s

My favorite places to get deep dish and thin crust Chicago style pizza. Personally Lou’s was my favorite for deep dish over the two, get the Malnati Chicago Classic (sausage, cheese, tomato sauce on butter crust). Also tried the Chicken Marsala Pasta at Lou’s which was amazing. Lou’s also had Italian ice which we tried lemon and strawberry – lemon being my favorite. If you go to Lou’s eat at the Gold Coast location, the area is super trendy. Giordano’s had my favorite thin crust pizza, so delicious.

Shake Shack

The midwest In&Out, super delicious burgers and the best crinkle cut fries. Also the black & white shake is delicious!

Wrigley Field Cubs / US Cellular Field White Sox

Not a huge cubs fan, but definitely a huge MLB fan. This stadium is so historic and amazing. Seeing the ivy wall was exciting since usually I only see it on television. We had a ton of fun at the game. Take the L Train there.

Chicago Riverwalk / Water Taxis – Architecture River Cruise

Probably one of my favorite things I’ve ever done in Chicago, the architecture of the skyline is gorgeous. We took the Chicago Architecture Foundation’s 1.5 hour tour and loved it, super beautiful on a sunny day.

Grant Park / Buckingham Fountain

Beautiful fountain located past Millennium Park. There are water fountain shows at night during the summer.

Millennium Park / Cloud Gate / The Bean

Iconic site of Chicago. The Bean is beautiful and it’s cool to see your reflection in it amongst the city scape. The area all around is extremely crowded and very touristy.

Arts Institute of Chicago

My favorite museum I’ve ever been to, this competes with The Met (NYC) and The National Gallery (London) for me. My favorite is the Impressionism paintings…love Monet & Van Gogh. featured my top 2 favorites at the bottom. The top 3 most famous artwork are American Gothic, Nighthawks & A Sunday Afternoon on the Island of La Grande Jatte.

Navy Pier

Cute pier with beautiful views, unique storefronts and wonderful restaurants. During the summer they have firework performances at night which was a fun date night experience.

The Original Rainbow Cone

If you go to Navy Pier, please try one of these iconic rainbow cones. Each layer is a unique different flavor, but of course my favorite was the top layer of orange sherbet. The stacking of the ice cream is so unique, I got it in a cup this time but next time I’ll try the cone.

Chicago Theater

Beautiful theater with rotating performances. Super pretty all lit up at night.

Magnificent Mile / Michigan Ave.

All the major mall stores on one giant street. I loved staying near this area, super convenient for souvenir/gift shopping and lots of restaurants to select from.

Joffrey Ballet

Would love to see a performance if I’m in Chicago during Swan Lake or The Nutcracker usually during October and December. Probably my favorite ballet company besides ABT in NYC.

Lincoln Park Zoo

One of my favorite activities we did in the city. The zoo & conservatory are both free admission to visit. We saw so many unique animals, my favorite were the giraffes and zebras. They even had a dippin’ dots stand – love the banana split flavor. Lots of fun exhibits and a great place to learn about all these crazy animals.

Lincoln Park Conservatory

Right next to the zoo is the conservatory, which has a lot of neat plants located in a greenhouse. My favorite room was the orchids. Felt super peaceful.

North Avenue Beach/Oak Street Beach

Personally think these are my favorite beaches in the city. You can see them both from the 360 degree observatory deck. Both are great, but Oak Street beach is the smaller of the two. My favorite is the North Avenue Beach which has the hook like peninsula. You can see the most spectacular close view of the city scape from this beach. Oak Street beach is near one of my favorite cities to stroll around, Gold Coast.

Garrett Popcorn Shops

If you’re ever in Chicago you have to try Garrett’s popcorn, official popcorn of the Chicago Cubs. They sell this popcorn in the stadium and all over the city. My favorite is the Garrett Mix which has both the cheddar cheese and caramel corn – perfect savory sweet combination. Eat it quick or it’ll become stale.

St Charles

Small charming town with beautiful nature and picturesque views.

Transportation – L’Train

Super easy to navigate and get from place to place in the city. Wouldn’t recommend using at night due to safety, but easy to use during the day.

Conrad Chicago (Hilton Hotel)

We stayed at the Conrad Chicago in the city off of the West Loop. Super easy to get to from O’hare by taking the blue line from the airport. Highly recommend this hotel, it’s gorgeous, the rooms were really really nice. It’s pretty central and located near all the shops on the magnificent mile.

Next Time Must Do’s:

Downtown St. Charles for Dinner

Joffrey Ballet Swan Lake Performance

Hope you all enjoy the windy city as much as I did!