Chicago Travel Guide

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/Willis Tower/Sears Tower

Really cool view of the city. We went at night to see all the city lights

SkyDeck Chicago / Trench Coat – Banana Republic

Giordanos or Lou Malnati’s 

My favorite places to get deep dish and thin crust Chicago style pizza

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. We had a ton of fun at the game


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


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


Magnificent Mile / Michigan Ave.

All the major mall stores on one giant street


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.


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


Next Time Must Do’s:

Lincoln Park Zoo & Conservatory

360 Degrees Chicago (John Hancock Observatory)

North Avenue Beach/Oak Street Beach

Shedd Aquarium

Jazz Club

Downtown St. Charles for Dinner

Joffrey Ballet Swan Lake Performance

Lou Malnati’s Italian Ice

Eat Garrett Popcorn – Garrett Mix Flavor (cheese & caramel)

Chicago Waterfront / Pullover – Vineyard Vines; Khaki Pants – Banana Republic; Boat Shoes – Sperry Top Sider

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

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