Chicago – The Perfect 3-Day Itinerary



The windy city has great history. After the fire of 1871, also know as the Great Chicago Fire, nearly 4 miles long and 1 mile wide of the city was completely destroyed. Chicagoans took this as a second opportunity to remake their city exactly how they wished. Today, the architecture is one of the best aspects of the city. But, skyscrapers, deep dish pizza and beautiful buildings are not the only things you can expect to find when you visit; and while you can easily spend your days in tourist-filled attractions, there are many hidden gems that will give your visit that special touch. Read ahead for a great 3 day itinerary in Chicago for first time visitors!

Day One

Magnificent Mile

This 13-block stretch of North Michigan Avenue boasts style, flavor, entertainment and fun. You’ll find hundreds of stores, restaurants, hotels and all kinds of entertainment. Walking around is half the fun!

Strolling through the Magnificent Mile!

Museums

Many to choose from, if you’re only going to visit one museum, the Field Museum is the one to visit. The world-famous fossil known as “SUE” is the largest, best-preserved, and most complete Tyrannosaurus rex ever found. Measuring 40.5 feet long from snout to tail and 13 feet tall at the hip, it’s quite a sight.

Navy Pier

A stroll through the Navy Pier ais a great spot to watch the sun go down.

Deep Dish Pizza

A visit to Chi-Town is not complete without indulging in the world-famous deep dish pizza. Lou Malnatis is one of the best deep dish pizza spots in the city. Giordano’s has several locations and is also a tasty option. Calling your order in is a great option as deep dish pizzas take about an hour to cook.

Day two

Drink in the Views

Grab a drink at the Signature Lounge at the 96th while enjoying the beautiful Chicago skyline.

Architecture Boat Tour

A really great way to enjoy the city from a different perspective and learn about its rich history. Loved by locals and tourists alike!

Great views from the boat tour!

Cloud Gate

Stroll through Millennium park and take pictures with the Cloud Gate. The bean, nicknamed because of its shape, is made up of 168 stainless steel plates welded together and highly polished so that there are no visible seams.

The infamous bean

Iconic Chicago Theater

A really fun stop! The Chicago Theater was built in 1921 is the unofficial emblem of the city and appears frequently in film, television, artwork, and photography.

The Chicago Theater

Day 3

Sky Deck

Such a fun adrenaline rush, located in the Willis (aka Sears) Tower. An elevator takes you up 103 floors in less than a minute. If that’s not exciting enough, the sky deck is a glass box with unobstructed views of the city right below. Perfect for thrill-seekers! P.S. If you go early, it will be less packed!

1.353 feet above ground in the glass ledge!

Rent Bikes

Divvy, Chicago’s bicycle rent program has hundreds of bike stations sprinkled through many parts of the city and are easily and inexpensive to rent (less than 10 bucks for 24 hours!). A great way to visit the city.

Divvy bike stations everywhere!

Neighborhoods

Wilker Park – a fun neighborhood!

There are so many neighborhoods, each with its own unique personality. Outside of The Loop, you will find the GoldCoast, Wilker Park, Bucktown, Logan Square and much more. To get a real sense of the Chicago culture and it’s multifaceted personality, you definitely want to visit these areas.

Strolling through Gold Coast

I’d love to hear about your favorite spots in Chicago! Let me know!

About The Author

Natalia

La Joly Vie is your ultimate destination for all things travel, motherhood, and style. As my family and I collect more stamps in our passports, I share my lessons and tips right here with all of you!