A trip to Chicago can be an exciting and unforgettable experience. Known as the "Windy City," Chicago is a bustling metropolis with a rich history, stunning architecture, world-class museums, and delicious food. I will be going over what I did on my trip, what I would do again, and what I would do better!
Before you plan your trip, you should look into the Chicago City Pass or Go City Pass to save some money on a bundle of attractions. Tip: Although the pass is a ticket to various attractions, some have to be scheduled ahead of time; some popular ones are on a first-come, first-serve basis. If you do not schedule ahead of time, they might not be available when you would want to use them. I schedule some two weeks in advance to get a popular slot available.
One of the best tips I recommend is staying in the tourist or downtown area. Although on the map it seems a short distance, it's really long way. Plus, it will save in the long run on paying for Uber or using public transportation into unknown areas at night.
One of the best ways to explore Chicago is on foot, taking in the stunning architecture and vibrant street life. Visitors can take a stroll down the Magnificent Mile, a stretch of Michigan Avenue that is home to some of the city's best shopping and dining options. You can also explore the Chicago Riverwalk, a scenic walk that guides you through various breweries and small bars and nice sight views.
We used the CTA train for transportation for the majority of our trip. The fare was only $15 per person for a 3-day pass to use both train and bus, which covered unlimited transportation. It is very easily accessible, and it goes through all the most popular places one needs to go to in the downtown area.
Hop-On Hop-Off Big Bus Chicago
You can never go wrong with a Hop-On Hop-Off Big Bus Tour. If at any point, you want to get refreshed from the heat or warm from the cold, or save a walk to the following attraction in the city, this is the right Bus for you! Tip: Certain places like the Willis Tower are not accessible by the CTA Train. This helps reach even the further out attraction places.
1. Skydeck Chicago at Willis Tower
One of the must-see attractions in Chicago is the famous Willis Tower, formerly known as the Sears Tower. Stopping here is a must, and I would do this again! The ticket purchase includes a museum tour breaking down the Willis Tower history, Chicago culture, food & celebrities that have come out of their hometown Chicago. Towards the end of the attraction, visitors can step out onto the glass-bottomed box that extends 4.3 feet from the Skydeck At 1,353 feet in the air.
2. Millennium Park
Another popular attraction is Millennium Park, a 24.5-acre public park in the heart of downtown Chicago. The park is home to several iconic landmarks, including the Cloud Gate sculpture, also known as "The Bean," and the Jay Pritzker Pavilion, which hosts free outdoor concerts and events. We didn't stay for any of the outdoor events but had fun walking around the park and taking some worth moment pictures.
3. Architectural Boat Tour
Taking an architectural boat tour is a popular way to experience the stunning architecture of Chicago. The city is known for its unique and diverse architecture, with styles ranging from Gothic to Art Deco to Modernist. The Chicago River runs through the city's heart, offering a unique perspective to take in the city's impressive skyline. The boat tour is the best way to see some of Chicago's aspects and sky rises.
4. Chicago Navy Pier
Navy Pier is a popular destination, offering a range of exciting attractions, restaurants, stores, and rides. Recommend trying out the Centennial Ferris Wheel - There is so much to do here you can never go wrong with a pleasant evening or sundown.
5. Museum of Ice Cream
Unlimited ice cream!? Yes and no, unlimited ice cream is included in the ticket purchase while touring the museum, a raspa as well plus also a chance to try a Chicago Hot-Dog Ice Cream Edition! I definitely recommend this if you are looking for your next top Instagram or Facebook photo or simply something to do during the daytime.
6. Starbucks Reserve
Spending an evening at the Starbucks Reserve is a must, especially for coffee enthusiasts. Not only will you be visiting the biggest Starbucks in the world with 5 floors full of coffee art, craft, and beans and more beans. You can enjoy the most perfected expertly crafted brewed coffee I have ever tried anywhere. I definitely recommend paying to take the coffee guide tour, although it's a bit pricey I highly recommend it, and has its perks. You get your own knowledgeable tour guide, and a chance to try unreleased coffee- plus it comes with free coffee of choice!
Psshh, The 5 floor is a bar!
For a taste of Chicago's famous food scene, visitors can head to one of the city's many iconic eateries. Here I will share my top 5 picks:
1. Giordano's Pizzeria is famous for its deep-dish pizza and has become a personal favorite now.
A trip to Chicago is not complete without trying a Chicago-style hot dog-a beef hot dog served on a steamed poppy seed bun, topped with yellow mustard, bright green relish, diced onions, tomato wedges, a pickle spear, and a sprinkle of celery salt. No Ketchup!
We recommend Relish Chicago Hot-Dog. They have various locations, but the one we recommend the most is the location at 315 S Michigan Ave, Chicago, IL 60603