Chicago: A Road Trip to the Windy City


By Yashy Selvadurai Murphy @yashyanthi & online at:


Chicago; cityview; travel


Chicago, home to the second busiest airport in the world, is rich in architecture and old world charm at every corner. Given its central location, Chicago is also a popular road trip destination for many North American families, which is exactly how we found ourselves snacking on pakoras in our Chevy Traverse as we set our sights on the Windy City.

Although there’s something for everyone, it’s suffice to say that Chicago is best experienced as a nuclear family. As with most popular cities, if you’re in a large group and hoping to explore the culinary delights, be prepared to make reservations well ahead of time, something a bit difficult to do if you have young kids along for the journey.

Otherwise Chicago is easy to navigate as a group, from visiting major attractions to navigating the popular EL train system, you’ll have no trouble.


MM Dreams

The heartbeat of Chicago can be felt on the famous Magnificent Mile and this is where you will want to stay, especially if you’re in town for a quick weekend visit. There are many hotels in the area but only one actually opens its doors onto Mag Mile, the InterContinental Chicago. If you’re a history buff, you’ll enjoy the old world elegance and original architecture that is still maintained throughout the property. This used to be home to the luxurious Medinah Athletic Club where male members of the Shrine Organization passed their active hours. IMG_20140606_110842

The original pool is still in place and you and the family can take a swim in the world’s first above-ground Junior Olympic-size pool. There are many historical elements, including original artwork and layers of gold leaf detailing throughout the property. Stay in the upgraded modern wing or experience the original charm (and more spacious rooms) in the historic wing! Just walk out the front door of the hotel and you can go from shopping to gazing up at well-known landmarks.


MM Bites

Gaylord: Hankering for a desi fix in steak town? Swing by Gaylord and order up some spicy dishes that will remind you of your nani’s cooking but with a twist. Get the okra and vindaloo!

Giordano’s: If this is your first Chi-Town visit, stuffing your mouth with a slice of deep dish pizza is a rite of passage. Arrive early, put your name on the list and place your order before going for a walk. It takes 45 minutes to make this pizza and the veggie is just as good as the meat one.

The Purple Pig: This busy hot spot can be difficult to get into, but if you’re looking to cheese, swine and wine, you need not look any further. A sure crowd-pleaser, there’s plenty for the pork lover and a good mix of alternate dishes for those that prefer to sway away from the swine.  IMG_20140606_120833-2

The Doughnut Vault: Chicago is home to many doughnut shops and really, how can you go wrong with these? You can’t! But if you’re looking for fluffy, melt in your mouth goodness, swing by here. Expect line ups on the weekends and yes they close shop once they sell out.

David Burke’s Steakhouse: Every street corner has a steakhouse and it’s no secret that Chicago is a meat loving city. With many great options, you really can’t go wrong but if you’re looking for the king of the bull pen, this is it!


MM Explores

Chicago Children’s Museum: A visit to Navy Pier to soak in the rays and explore the carnival scenes should make you want to visit the Children’s Museum where little ones can expel some energy, engage in pretend-play and learn some science while they’re at it. Those with infants, toddlers and tweens will all be taken care of here.

360: Formerly known as the John Hancock Observatory, 360 Chicago is where you can ride up to the 94th floor, absorb the sheer wonder that is Chicago and if you’re feeling adventurous, TILT outwards and soar over Magnificent Mile. Note that only those over 40 inches can TILT but kids can run around and enjoy the 360 views. Catching a sunset here should definitely be on your list.

Art Institute of Chicago: One of the greatest Impressionists collections outside of Paris can be found here, and if you’re looking for a personal experience of the classic American Gothic, this is where you want to be. Great on a hot day as you can spend quite a few hours perusing the collections. Kids; Travel; Chicago

Millennium Park and Cloud Gate: No visit to Chicago is complete without clicking a billion pictures of the “Bean”. Have fun with Anish Kapoor’s sculpture, capture the reflection of the skyline and then pop over to the park behind. If you’re lucky, you can catch a free movie or concert!

Shoreline Sightseeing: There’s no better way to watch the fireworks than catching a Shoreline Cruise. Board right off Michigan Avenue or the Navy Pier, take in an architecture cruise that will not only give you the history of the many landmarks and architectural marvels, but will also end with you gazing up at the sky mesmerized by the fireworks. A perfect way to end the night!


Chicago is a true cultural hub that will please artists, architects, culinary fiends and historians. This city is very family friendly and don’t be surprised if you find stroller parking and change tables wherever you go. Chicago is also a city with plenty of free entertainment, just be sure to avoid any major conventions by checking the Choose Chicago calendar to determine the best time to visit.

This summer, why not head off on a road trip?

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