Finding New Roads: Family Road Trip to Chicago

Third time’s a charm, well in our case it’s the best one yet!

Ever vacation to a big city and fall in love with it immediately?  This is us with Chicago, and it’s not just me that loves it, we all do as a family, so when we were planning a family road trip with our close friends, Chicago was on the top of our list!  They had never been there so it was nice to share some of our favorite places and discover some new ones too.

Family Road Trip 2018! Chicago. Picture Taken at Millennium Park, Chicago
Family Road Trip 2018! Chicago. Picture Taken at Millennium Park, Chicago

If you have never been to Chicago, I hope this blog makes you add it to the list of must see places, I’m going to share with you some of the highlights of our trips, the best places we found to eat and all the stuff we did with the kids.

When I shared on my instagrams stories that I was heading to chicago, a lot of people asked me if it was safe enough to go with the kids and my answer is absolutely yes. I mean, like any other big city there are worries, you need to be smart about how you travel and where you go, but I never once felt worried or scared for our safety.  Chicago reminds me of my own city Toronto, just seems bigger with more shopping, more architect and one of the best cities for foodies!

From shopping, to architectural buildings, beautiful parks and amazing eats, Chicago offers a bit of everything for everyone!

The drive!

Lets start off with our decision to take a road trip versus flying there.  As the kids get older, roads trips have become one of our favorite things to do.  It gives us a chance to explore different cities, allows us the convenience of having a vehicle but most of all I don’t feel rushed.  There is no plane to catch, so we can take our time, plus it gives you extra space for shopping without trying to shove everything in a luggage.

My biggest worry when taking road trips is safety, I mean we are going to spend a lot of time driving so you want to make sure the vehicle you are taking is fully serviced and ready to be driven for a lot of kilometers/miles.  

Chicago Family Road Trip! Most important pit stop- COFFEE! Driving the new 2018 Chevy Traverse!

For this trip, I partnered up with Chevrolet Canada and had the privilege of driving the new 2018 Traverse. Voted as the most dependable midsize SUV, the traverse immediately made me feel safe, and since I would be doing all the driving this was important to me.  The Traverse has On-Star, which provided me with some relief knowing that should anything happen, like us getting into a car accident that we were connected immediately with first responders. The Navigation system was amazing, it calculated traffic, identified food and gas stops and the voice prompts were accurate and with advanced notice. I hate when the alerts are said at the last minute, especially when driving in a very busy city, but “Shelley” (thats what we named the voice of the navigation) was awesome! Some of the other amazing features I loved about the Traverse were: the lane assist, rear vision camera, rear parking assist, lane change alerts with blind zone alerts and low speed forward braking.

How beautiful is this 2018 Traverse!
Chevrolet Traverse, comes with full navigation system, On-Star & WiFi
Chevrolet Traverse, comes with full navigation system, On-Star & WiFi

The BEST feature was the wifi! (yes, the Traverse came with wifi)

Travelling with kids can be challenging, they get bored quickly and restless.  I am happy to say that my boys did not complain once the entire drive there or back. They watched their favorite shows, played games, listen to music and watched movies. The didn’t argue one single time- not once!


The drive from Toronto to Chicago took us 8 hours and 45 minutes, with 4 stops along the way for bathroom breaks, eating and 1 stop for gas- yup, we only stopped for once to fill up on the way there.  The drive back took longer as we left mid day and there was a lot of traffic, plus we took a long dinner break. The drive home took us 12 hours and we spent a total of $215.00 on gas for our whole trip, this includes using the Traverse in Chicago. Not bad for a big truck!

Our road trip to Chicago made me realize that I need a Traverse in my life on a daily basis, especially since the majority of my business is spent travelling between clients with a car full of workout equipment.  My lease is up next year on my current car, and the Traverse is on the top of my list. It was so hard to give it back, but I am so thankful for the opportunity to work with Chevrolet Canada they were amazing in every aspect.

Look at the space of Traverse’s trunk! A Personal Trainers Dream!

The Hotel!

Okay- next- lets talk about our hotel!  We stayed at The James Hotel. We had stayed there previously, we had such a great experience the first time that we wanted to stay there again,  but the recent change in management left us a little disappointed. Although the staff were amazing, the management of the hotel was not. There we additional hidden fees that are not disclosed when booking, they charged us an additional $20 a day for ‘facility fees’ on top of the final price. Because we had paid in full when we booked, these were then added on upon checkout, however because of the other unfortunate errors they did end up waiving that fee. Listen, I’m okay with paying whatever fee you have, I just like to be told about it in advance. Overall we had a good stay, some other hiccups but nothing major. Would I stay there again? Yes, but I would probably try a new hotel next time!

If you are thinking about heading to Chicago, pick a hotel that is on or close to Magnificent Mile.  It puts you in the centre of everything, and within walking distance to all attractions.

Here is a list of all the must see places and the amazing eats we had! From adults to all the kids, these are the places we loved the most! (Kids ages were: 13, 11, 10, 8)

Chicago’s Must see places:

  • Millenium Park
  • The Bean
  • John Hancock Building
  • Navy Pier
  • Chicago Riverwalk
  • Art Museum

I’m just going to let the pictures do all the talking!








City Art

Chicago Eats

  • Quartino ( This is a must in Chicago): Our favourite restaurant EVER! 
  • Eataly:  From Gelato, to espresso, pizza, fresh pasta, focaccia- Eataly brings you a whole lot of Italy and it’s delicious!
  • True Food Kitchen: This restaurant went above and beyond our expectations. It’s a scratch kitchen, which means everything is made to order- EVERYTHING! It takes a bit extra time to get your food, but trust me it is worth it.  From Organic wine to vegan Ricotta, the entire menu offered organic fresh foods and was able to meet all dietary restrictions and allergies.  From the food to the service, this was the favourite new restaurant by far!
  • Howells & Hood: Beer and Fish Tacos- I’ll just leave it right there for you!
  • Eleven City Diner: Best Pancakes hands down in USA!
Sangria at True Kitchen, Chicago
Sangria at True Kitchen, Chicago
Dinner at Quartino, Chicago
Dinner at Quartino, Chicago

Working out while on vacation:

If you followed along my instagram stories, you know that I workout even when I’m on vacation, even though the James Hotel had a nice, fully equipped gym, the Chicago River was so beautiful and peaceful that I ran along the river walk every morning instead (4.5 Km).  

Morning run along the Chicago River Walk
Morning run along the Chicago River Walk

And for all you fitbit lovers, we  clocked in an average of 23,000 steps per day! Crazy right?

We were sad to leave, everyone could always use a few more days, but we packed in as much as we could in 3 days! The moms loved it, The dads loved it and the kids loved it so we couldn’t ask for a better family Road trip destination! So if you’ve been thinking about visiting Chicago- do it! you won’t be disappointed (promise)

Good bye Chicago till next time!



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