Since living in Illinois for nearly a decade, we continue to enjoy a family trip to Chicago as often as possible. Anytime family or friends visit from out of town, they always ask to visit the Windy City.
Although I am still an amateur at knowing all the amazing things Chicago has to offer, I am getting better at navigating the city. Recently, I took my nieces on a family trip to Chicago for two days. If you’ve read my blog post 48 Hours in Texas, you know I love to take fun weekend trips.
riding the train to the Windy City
We are a short train ride to Union Station in downtown Chi-Town. I love Union Station with all of its architecture and history. Side note–there are many movies that have scenes shot in Union Station including The Untouchables and Man of Steel. The girls had a great time watching some of the clips on Youtube while standing in the exact places the movies were filmed.
When the girls stepped out of the train station for the first time, they were speechless when they saw the tall buildings, the busy streets, and all the people. They were instantly in love! This family trip to Chicago was starting off perfectly.
We stayed in the Gold Coast area, which is the northern part of downtown. This area has lots of shopping, fancy cars, and fancy hotels—the girls were in awe.
the best area to stay for a Family Trip to Chicago
We stayed at the Hilton Chicago/Magnificent Mile Suites. I got a great deal at our hotel, and it was just a few blocks away from the Hancock Building, the beach, great shopping, and Giordano’s Chicago-style pizza! The hotel was a two-room suite, so we all fit very comfortably.
I am a Hilton Honors member (free to sign up!), which is how I landed such a great deal on the room. Every time you book a room using your Hilton Honors reward number, you get a discount on your room! Hilton has great rooms and offers AAA discounts, government discounts, and military discounts.
We went directly from the train station to check into our hotel. It was 10:30 a.m., so our room wasn’t ready, but for a couple of dollars, we were able to check our bags and leave them so we didn’t have to lug them around the city.
sightseeing around the Windy City
We began our family trip to Chicago with sightseeing at the John Hancock Building. Here, we purchased a package of three tour options called the Go Card Chicago, which is a great deal. They also offer an option to visit four or five attractions, but for a two-day trip, we decided we could only squeeze in three attractions and still have time for shopping and other free sightseeing options. There are also coupons for tours in Chicago on Groupon.
We went to the 360 Chicago Observation Deck on the 94th floor of the Hancock Building. The view is breathtaking and the lines to get in are much shorter than Willis Tower (formerly known as the Sears Tower). And to be honest, the views of Michigan Lake and the city are essentially the same from both buildings. Two of my nieces did the Tilt on the Observation Deck, but the rest of us were too chicken!
delicious food and retail therapy
After our visit to the Hancock Building, we had to hit up some famous Chicago-style deep dish pizza at Giordano’s. It was ahhh-mazing! I try to stay away from carbs because of dietary restrictions, but I just can’t help myself with Giordano’s. The girls absolutely loved it.
Next, we indulged in a little retail therapy on our Chicago trip. The main attractions for my young nieces: PINK on Michigan Avenue (also known as the Magnificent Mile) and the LUSH store. Thankfully, they are right next door to each other. The PINK store is one entire floor above Victoria’s Secret. Luckily, we were there for the semi-annual sale, and the girls got some serious bargains.
If you have never been to a LUSH store, you are missing out! They have handmade health and beauty items including hair care products, bath bombs that are to die for, face products, really…just about anything your heart desires in the health and beauty world! Another bonus is that they use all-natural ingredients.
more sightseeing on our Family Trip to Chicago
Since everything was in such close proximity, we dropped off our shopping bags at the hotel and walked to the beach. The Lake Michigan beaches are absolutely gorgeous. And free admission!
Our next stop that same day was Navy Pier. We grabbed a quick bite to eat and then we went on a Lake Michigan boat tour. The tour was part of our package of three attractions we bought. The boat ride went up and down the shoreline of Chicago and provided spectacular skyline views and historical information about Chicago. We chose to do this tour right at sunset for some fantastic photo ops.
The next day, on our way to breakfast, we saw a movie being filmed. Michigan Avenue was blocked off and a helicopter was filming aerial views with a huge camera mounted on the front. It was such a fun and unexpected surprise to have the opportunity to see this. We stood there for a short time, with all of the other spectators, just watching this helicopter maneuver in between such large high-rise buildings.
Breakfast was my treat to the girls in the Signature Room at the John Hancock Building. It was a brunch buffet with the most exceptional food. Lots of seafood, omelets made to order, a dessert bar, fruit and cheese, salads and so much more. It was crazy how much food we ate!
Next, we hit the beach, because Chicago has some gorgeous beaches on Michigan Lake. The girls played beach volleyball and swam in the lake. At the end of the two-day trip, they said the beach was their favorite.
can’t miss attractions on our Family trip to Chicago
Our final attraction was an architectural river tour. It’s a boat trip up and down the Chicago River that talks about the history of Chicago and the various buildings along the riverfront–when they were built, the style of architecture, etc. The boat tour is such a great way to learn about the history of Chicago, including the Great Chicago Fire of 1871.
We hit a few more shops, Garrett’s Popcorn (if you visit Chicago, you have to go to Garrett’s!), and then stopped at Cloud Gate, also known as “The Bean.” The Bean is located in Millennium Park and it was super crowded the day we were there.
More Attractions in Chicago
If you have more than two days to spend in Chicago, there are so many fun things to do. There are world-class museums, sporting events, amazing food, and the list goes on and on. Here are some of my other favorite attractions in the Windy City that are fun for the whole family:
- Skydeck Chicago
- Shedd Aquarium
- Adler Planetarium
- Art Institute of Chicago
- Lincoln Park Zoo
- Museum of Science and Industry
- Wrigley Field
saying goodbye to the windy city
After The Bean, we picked up our luggage from the hotel and headed back to Union Station to catch the train. I feel like our family trip to Chicago was a success, because my nieces are already planning their next trip to go back to the Windy City! If you are considering a Chicago family vacation, it is a great place for the entire family because there is something fun for everyone.
Let me know what is on your must-see list when visiting Chicago.