How to Spend 3 Days in Chicago

I just recently traveled to Chicago, Illinois!

I have always wanted to visit the Windy City (in the summer, because who likes -30-degree temperatures and many feet of snow?) but I have not gotten the chance until now!

I brought the sunshine and warm weather with me from New York for my week in Chi-Town.

Thursday 5/23

I walked eight miles my first day in Chi-Town. I saw it all! We started off at the River Walk, a brand new beautifully landscaped and designed seating and bar space along the Chicago River.

I then walked to Millennium Park, where I saw the infamous Bean. 

J.Crew Factory chambray shirt | American Eagle tall jeggings | Tory Burch double pearl earrings | Tory Burch gold logo bangle | J.Crew Factory New York pink and white scarf (similar) | Rocksbox Aster dawn ring | Ray-Ban tortoise shell Wayfarers | Sperry classic boat shoes | Tory Burch pink satchel

We took a beautiful walk along Lake Michigan, until stopping at the third largest fountain in the world, Buckingham Fountain.

Shedd Aquarium was the next stop on our adventure around town. My mom said I had to go see the aquarium. I do not even remember the last time I was at an aquarium, so it was a nice change of pace. The tickets were $40 a person, which was outrageously expensive to see some fish and some jumping dolphins. I would not recommend. Rather, we should have gone to the Chicago Art Institute, but maybe next time.

The best views in the city are from the grassy area between the Shedd Aquarium and the planetarium. 

Later we took an $8 water taxi from the aquarium to Navy Pier which put us on route for dinner at 312 Chicago. A delicious Italian restaurant that I found on OpenTable.

I have never picked a bad restaurant with Open Table regardless of what city or country I am in.

Friday 5/24

Let’s go Cubbies!

We took the “EL” or elevated train, or for New Yorkers, an elevated subway, right into Wrigley Ville, the home of Wrigley Field.

It is clear that only people under the age of 30 live in Wrigley Ville. It is a hip and trendy area of the city filled with bars and young college grads. Some of the town-houses outside of the green, 30,000 seat sized baseball park have roof top seating where Cubs fans can buy tickets to sit on top of these houses on bleachers and watch the game from the outfield. It was so cool.

The temperature and wind were chilly, which did not help our bitter loss to the Cleveland Reds.

But we were warmed by the sweet and friendly people inside the stadium.

The staff was so pleasant and was so smiley.

Our neighbors in our row were also so friendly and welcoming, I felt like the Cubs fans were my friends rather than strangers.

After every run, everyone would stand and high five each other. It was very cute and sure warmed me up.

So did the deep dish or “real” pizza I had at Giordano’s after nine innings. 

I thought New York had the best pizza in the world, and then that was confirmed when I tried deep dish.

Deep dish was almost like eating a big cheese, sauce and meat pie. It was delicious, but not my favorite.

I am glad I had the full Chicago experience with deep dish pizza, but I will stick to my cheese slice for $3 in New York.

J.Crew gingham faux wrap dress (same dress in different color) | Mango denim jacket | Baublebar pink tassel earrings (similar) | Tory Burch gold logo bangle | Rocksbox Aster dawn ring | Ray-Ban tortoise shell Wayfarers | Longchamp le pliage large shopping tote | Jack Rogers sandal in white

Saturday 5/25

Saturday was probably my favorite day in the city. We walked the full length of the river walk, where I almost got swept away by the wind, before arriving at our architecture tour with Chicago River Boat Architecture Tour company.

By the time we got to the boat we were dripping in sweat.

Once the ship set sail, the Windy City cooled us off and gave us a bit too much sun while we learned about the city with the first skyscraper and former tallest building in the world, the Sears Tower.

Currently known as the Willis Tower, Sears Tower, is now the 17^th tallest building in the world.

The architecture was beautiful, and I learned so much about the city.

I loved how all of the windows on each building reflected the sky and the clouds.

This tour was so interesting, and I would 10/10 recommend.

To cool off from the boat ride, we went and got some Ben & Jerry’s on Navy Pier. We got to see the beautiful skyline and had great views of the aqua colored lake.

Lake Michigan looks like it could be an ocean. It is so large you cannot even see the other side of it.

We walked along the other side of Navy Pier towards dinner and saw families and kids swimming and lounging by the lake.

Dinner was at Ditka’s, off of Michigan Avenue, the 5^thAvenue of Chicago. Mike Ditka, former Chicago Bears coach, or as I know him from Kicking and Screaming, the kid’s soccer movie starring Will Ferrell, is the proprietor of this restaurant. 

Chicago was absolutely beautiful (in the summer, not sure how pretty it can be in the winter)!

I am a city girl, so of course I loved this new city.

It was sparkling clean. Chicago is the best of both worlds, beach and city!

 I loved being near the water. 

Chicago is not that big of a city, so I felt like I got a really good taste for the Windy City in 72-hours.