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Last Chance to Enter to Win a Chicago Staycation!

Giveaway and Tips for a Great Staycation

By Sara Yaniga, Macaroni KID Chicago April 9, 2023

Chicago is a popular travel destination for people all around the world to visit, but it makes a great staycation destination for locals too! Here are five things to consider when planning a little local adventure for your own family and don't forget to enter to win our Chicago Staycation Giveaway!

1) Accommodations - Consider the size of your family, budget, and travel habits before booking a room. While our family of four used to be able to comfortably fit into a standard room with two beds, as our kids grow, so do our needs. We will compare options for adjoining rooms, suites, or rooms that can accommodate a rollaway and consider our own enjoyment as well. If one of the goals of this staycation is for the adults to actually get a little relaxation or enjoy a cup of hot coffee in the quiet morning, then it's important to make sure your sleeping arrangements match your needs as best they can.




2) Location - There is so much to see and do while in Chicago, even for those who live in the city, so location is important to consider. When we travel as a family we try to pinpoint a spot to stay that is convenient to the places and things we want to experience, but also has amenities nearby that are perfect for a family - such as a place to walk, play or just relax.  Restaurants to grab a bite to eat or shops in case you need more diapers, wipes, or a last-minute souvenir for the neighbor feeding your fish back home. 

3) Really "See" Chicago - When people ask what I think are "musts" for a visit to Chicago I always say that there are two ways to get a great view of this city. One is from the water and thankfully there are multiple great river tours operating from the docks by Michigan Avenue or from Lake Michigan. The second is to get up high and take in the view from Skydeck Chicago. This is actually something our family does nearly every year, even if we don't have family or friends in town for a visit. Chicago is alive and always changing and that view from the 103rd floor of the Willis Tower never gets old. Plus, if you haven't been in a while, then the interactive Skydeck Experience (added in 2021) shares Chicago facts, highlights, and history as you make your way toward the elevators. 

4) Explore Something New - In 2021 we discovered the Museum of Illusions and my children have been asking to go back ever since. It is really easy to get to since it is only a couple of blocks away from Millennium Park, right on Washington and Wabash. This is a smaller museum but it packs a mighty punch when it comes to the entertainment factor. Plus, hidden in all that fun is a little education and workout for your brains, but I won't tell the children if you don't! MOI Chicago is also a great spot when you have a variety of ages to entertain. I am so glad we didn't walk by the door that day and we gave something new a try because it is worth visiting more than once!

5) Connect to Your Destination During Down Time - I love reading and traveling so it won't come as a surprise that I try to use books to connect myself, and our family, to a destination. Now, you may be thinking, "I'm from Chicago, (or the Chicago area) and I am already "connected" to the destination!" but I ask you to hear me out. Remind yourself that just because you may know about the lion statues at the Art Institute, or which museums were part of the World's Fair, and what really goes on a hot dog - our kids may not! So I love to grab a book, something not too heavy so I can easily carry it around with us, and pull it out when we want to take a break to rest or grab a bite to eat. Hide & Seek Chicago is a great one for this very scenario and I like that each section is a two-page spread so more than one kid can enjoy it simultaneously.

6) Tour Freely - This city offers tons of free, or low-cost, entertainment! Here are some of our favorite places and things to experience when playing tourist in our own city:

  • Lincoln Park Zoo, Farm, and Conservatory (FREE)
  • Chicago/Illinois Resident Free Admission Dates at Museums (Proof of Residency Required - Check Calendar for Dates.)
  • Garfield Park Conservatory (FREE)
  • Art on the MART (FREE)
  • Check out a Museum Passport from the Chicago Public Library which is good several museums, zoos, and gardens (FREE)
  • Explore Northerly Island (FREE)
  • Ride the "L", the Brown Line offers especially great views of the city when heading toward the Loop (Kids under 7 are FREE)
  • Take a Water Taxi from Michigan Ave to Chinatown (Kids 3 and under are FREE)
  • Play mini golf, ride scooters and climb on the playgrounds inside Maggie Daley Park (Mini Golf is FREE for kids ages 4 and under with $12.00 adult admission and scooters are available to rent; prices vary)

If you haven't caught on - I am a fan of our city and all it has to offer families which is why I want to give one subscriber a great Chicago Staycation Vacation! Click this link, or use the form below to enter for a chance to win! 

One winner will be randomly selected to win the following:

- One Night Stay in a Swissotel Chicago "Kid Suite"

Swissotel Chicago's special "Kid Suites" which is perfect for every traveling family! This two-room suite offers a room just for the parents and the second is set up just for the "VIK" (Very Important Kids) guests with special bedding, toys, books, and surprises to make them feel at home and extra special. As an added bonus, the Swissotel Chicago is conveniently located with access to the lakefront, the parks, Mag Mile and so much more - like the amazing Lake Shore East community which has a great park, playground, restaurants, and shops steps away

- 4 Passes to Skydeck Chicago 

The Skydeck is open year-round, seven days a week. The viewing tower is popular with locals and visitors alike and offers unparalleled views of Chicago and beyond. Are you brave enough to step out onto The Ledge while you are there?

4 Passes to the Museum of Illusions Chicago

Prepare yourself to hear your family utter, "How in the world?!?" more than once while exploring this popular spot! Experience the classics and the never-before-seen illusions and brain teasers. Immerse yourself in an intriguing visual, sensory, and educational experience!

Hide & Seek Chicago Activity Book

This 32-page book is the perfect size to bring along when you want to have a little downtime, or perhaps are waiting for a table at your favorite lunch spot. It will keep kids entertained and engaged in exploring the Windy City. Also included is a small sketchbook and colored pencils to perfect for entertaining kids during downtime or for jotting down notes or sketches of things they saw during their staycation adventure!


To see complete giveaway rules, please click here. One entry per person, duplicates will be removed.  Winner will be selected at random and have 48 hours to respond and collect prize. Failure to respond in time will be a forfeit and a new winner will be selected. Must be 18 years of age and a subscriber to Macaroni KID Chicago.