Things to do in Chicago – A Chicago 3 Day Itinerary

Chicago is more than hot dogs, deep dish pizza and bitterly cold winters. It’s a city of mesmerizing architecture that’s best seen on a boat cruise and has a pace that’s less intimidating than other major cities in the United States. There are so many thins to do in Chicago. Just 3 days in Chicago gives you a taste of the city that will have you coming back for more. I recently spent a three-day weekend in the Windy City and can’t wait to share my Chicago 3 day itinerary with you. I am Erin Jones, of Adventures of Erin, a full time corporate worker and avid traveler. I share a lot of my adventures on Instagram, @londonerin.

My Chicago 3 Day Itinerary includes:

• Getting to Chicago
• Where to Stay in the Chicago Loop
• Things to Do in Chicago Loop
• Eating in the Chicago Loop

I’m based in the middle of the United States and searching for something unique; I planned a Chicago 3 day itinerary that started with a seven-hour journey by train!

Getting to Chicago

Yes, I could have taken a plane and been to Chicago in an hour, but I went for the scenic route to see more of the countryside and save a little money.  I didn’t miss the security lines and cattle herding to get to my gate but did have to get to the station early in the morning. The Amtrak train originated from California and picked up Kansas City passengers at Union Station.  I had a reserved coach seat and was surprised at the roominess even with the passenger in front of me leaning back to sleep. Gazing out the window and watching the countryside pass by was peaceful. If the train car gets a little loud or you need a change of scenery, the observation car provides an alternative place to sit and relax.  With larger windows, you have a bird’s eye view of the world around you.

I arrived at Union Station Chicago around three in the afternoon and checked into a hotel central in the city.  I wanted to be in the center so that I could walk to the sites with ease for the duration of my three-day weekend.  Chicago is known to be a city of neighborhoods, and the Loop is downtown where the spiderweb of commuter trains known as the “L” all convene.

Where to Stay in the Chicago Loop

Right by the Chicago River I stayed at the LondonHouse hotel.  The architecture on the outside is from the art deco 1920’s but inside its been modernized with dark wooden fixtures and velvet green couches.  Upon entry to the hotel the check in desk is on the second floor. The staff was friendly and the check in process was quick. For the best views, request a river facing view from at least the 17th floor. 

The rooms are all a great size with luxurious sheets and a comfy bed. I hit snooze when I planned to explore the city.  Each room has an espresso machine and giant television for additional comfort. Bathrooms are roomy with tile floors and the fluffiest of towels. Artwork in the room is of local Chicago sites that further inspired my exploring.

You don’t have to leave the hotel to have one of the best city scape views.  If you head up to the 21st floor there is a trendy rooftop bar that’s a hit with the locals.  It’s great people watching to see the line of trendy millennials anxiously awaiting their turn.  As a tenant of the hotel, you get first dibs and do not have to wait in line, just show your room key to the attendant and you’re on your way.

From the rooftop there is a scenic view of the Chicago River and the local architecture it’s known for.  Architects construct buildings to match the local area so even though each building is unique they meld together for a dazzling city scape. On certain summer evenings, there are fireworks on the Navy Pier that can be seen from the rooftop.  

If crowds aren’t your style, I went up to the roof in the morning and had the place to myself for picturesque views of the skyline and river below.

You can reserve the best price on your room at London House right now!

Things to Do in Chicago

After you’ve discovered the rooftop and the amenities of the hotel, it’s time to start exploring. There are so many options close by the hotel that you can definitely spend your entire three days in Chicago.

Get Creative at the American Writers Museum

The American Writers Museum is located on Michigan Avenue and is devoted to the many American authors who have contributed fiction, non-fiction and music.  Currently there’s an exhibit on Bob Dylan that describes how his music transformed the folk music scene. The exhibit provides headphones so that you can listen to the many songs written along with how other musicians recreated some of his songs.  There’s also information about his Nobel prize for literature. You can read through the book that outlines his speech.

My favorite part of the museum is the typewriter room.  The click clacks of the typewriters as visitors start the next great American novel is satisfying. The museum provides paper so you can start your own story or even continue one from the previous visitor. There is a collection of typewriters including John Lennon and Ernest Hemingway.

Next, there’s a computer that allows you to pick from your favorite American authors and create a bookmark that’s emailed to you.  Once you select the author, the computer displays how your favorite ranked among the top authors of other visitors. My only author to rank top 10 was Louisa May Alcott, the author of Little Women.

The museum is filled with inspiring quotes of authors and provides much needed motivation for those aspiring to be a writer too.  I ended up spending about an hour at the museum and really enjoyed it. The exhibits are interactive, and I learned a lot about American writing and those who contribute to it.

Millennium Park

Next on my Chicago itinerary was Millennium Park, only two blocks from the Writers Museum. Millennium Park is home to the Cloud Gate sculpture affectionately known as the “Bean”.  The sculpture was created by British born Anish Kapoor. It’s polished surface beautifully reflects the skyline and visitors. The area does get crowded with selfie takers, but everyone is friendly and its fun to join in. For less crowded photo taking, come early in the morning and you’ll almost have the place to yourself.  

Also, in the park is Crown Fountain, a splash park enjoyed by kids and adults alike.  The fountain has two parallel towers that change faces periodically. Eventually the pictures change, and it appears as if the people are spouting water out of the fountain.  Obviously, the fountain itself operates during warmer months but the people projections last all year round. Entry to the park is free and on a good weather day, there’s plenty of benches to relax and people watch and enjoy the surroundings.

Compete at City Mini Golf

Right in the city center you will also find City Mini Golf, a mini golf course in Maggie Daley Park which is adjacent to Millennium Park.  The mini golf course offers a fun course with the first half of the holes dedicated to Chicago landmarks. Trying to putt through a Chicago Bulls basketball hoop is challenging but the staff will give you a sticker each time you get a hole in one.  I loved playing the game right in the middle of the city as the skyscraper views were spectacular. The course is a full 18 holes and was a bit challenging leading to a fun competition with friends and plenty of laughs at our lack of skill.

Get Cultured at the Chicago Art Institute

Across the street from Millennium Park, you can’t miss the imposing Beaux Arts style Chicago Institute of Art. Even if you are not an art lover, the museum deserves a place in your Chicago 3 day itinerary. Ranked #2 among all museums in the US, and in the top 20 worldwide, the Art Institute attracts visitors from around the world. If you are expecting nothing but walls of paintings, you may be surprised by the variety of art types featured including baroque home furnishings, ceremonial wear of indigenous peoples around the world, and an extensive collection of Japanese and Chinese arts.

Look for a full article on spending a layover at the Chicago Art Institute here on Gypsy With a Day Job soon! While you are there, look across Michigan Avenue to see the starting point of westbound Route 66.

Be Wowed at the Chicago Cultural Center

Just down the street is the Chicago Cultural Center, a historic building that used to be the public library.  The center is free to visit and has exquisite tiled ceilings and dramatic staircases. Within the building is a dome made from Tiffany glass.  On a sunny day the colors shining through are magnificent with roses and blue outlines, it reminded me of cathedrals in Europe. The Cultural Center holds many events for the public but on the day, I went it was great for wandering around enjoying the beauty around me.

Explore Navy Pier

Venturing past the same block where I’d spent the first part of my Chicago 3 day itinerary, I found myself at the Navy Pier.  The pier is family friendly with a wide range of fast food restaurants and souvenir shops. You can also ride the giant Ferris Wheel, the Centennial Wheel. Although there are plenty of places to ride, it is especially appropriate here, as the world’s first reduced steel Ferris Wheel was invented for the Chicago World Fair of 1893 by structural engineer George Washington Gale Ferris Jr.

Enjoy a Chicago River Cruise

I ended up taking a Seadog Cruise that held around 50 passengers and was a speed boat that zipped around the lake before cruising up the river.  Observing the architecture by boat is fun and an easy way to see which part of the city you might want to explore more. The river used to be very dirty and not a pleasant place to be. Recent efforts have cleaned up the river and more cafes and businesses are opening on the riverbanks, and now the cruises are an essential part of any Chicago 3 day itinerary.

The cruise I took was just over an hour and didn’t cover as much territory as some other cruises do.  For a more in-depth overview of Chicago and the architecture, I recommend the Chicago Architecture Tour which departs from a dock right off Michigan Avenue. Although it may cost a bit more you do end up learning more about the architecture and the growth of Chicago.

Indulge

After enjoying the boat cruise, I treated myself to a bit of pampering at Trixie Girl Blow Dry Bar.  Tucked away in a building right on Michigan Avenue, the salon is small and focuses on washing, drying and styling your hair.  They offer makeup services too if you want to get jazzed up for a night on the town. I went for a classic blow dry and felt like a million bucks afterwards.  The stylists were efficient, and it only took 30 minutes from start to finish. To be honest, I should have checked the weather forecast as my stylish curls soon fell after some rain moved in.  Overall it was still an excellent experience I recommend for girls or solo travel trips!

Eating in the Chicago Loop

Stan’s Donuts

Who doesn’t love a donut? Stan’s Donuts with several locations within Chicago will have a line but it’s worth the wait.  They offer a variety, with my favorite being an orange old fashioned. The orange flavor in the cake donut is the perfect amount of citrus and sweet.  This was the first donut shop where I had seen this flavor and was anxious to try it.

Stans’ interior is perfectly pink and inviting to stay awhile as you munch on the sweet treats.  There’s a great mix of patrons from families to the millennial crowd ready to update their Instagram. The menu ranges from Standard, Specialty and Dough Boy’s best with the prices increasing with the fancier the donut you pick.  I must admit I was a repeat customer and will be sure to stop in on my next Chicago visit too.

Garrett’s Popcorn

Right next to Stan’s on Michigan Avenue is Garrett’s Popcorn.  Creating popcorn snacks since 1949, Garrett’s is a Chicago institution. You must have some during your 3 days in Chicago, and it’s an excellent treat to bring back home for family and friends (if you manage to save some).  The Garrett Mix is what’s most popular and is a combination of Caramel and Cheese corn. It’s a great balance of salty and sweet and my number one choice.  They have other flavors like caramel pecan and plain that the staff will allow you to sample. You’ll walk into Garrets and receive a friendly smile and prompt service, but as its one of the more popular shops in Chicago, gather some patience for a wait. 

Giordano’s Pizza

I would be remiss if I didn’t mention deep dish style pizza.  Every local has there favorite and there’s plenty of options to choose from.  For your 3 days in Chicago, Giordano’s has a location close to Millennium Park and Michigan Avenue. Around since 1974, you’ll get the traditional deep-dish pizza overflowing with cheese, tomato sauce and toppings of your choosing.  Even with a small pizza, it’s very filling so bring your appetite.

Winding up My 3 days in Chicago

After my 3 days in Chicago, it was time for me to return back home on the train.  I was once again amazed at how smooth it was to board the train and save some time without airport security lines and potential delays.  I left Chicago in great spirits as I tried to learn a little bit about the city with each moment. From great food, luxurious hotels and amazing architecture, a Chicago 3 day itinerary is a perfect getaway.  I hope you get to experience it soon!

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About Erin Jones