Chicago is that perfect middle spot for most North Americans living on the East Coast and for us Torontonians, Chicago is only an eight hour drive away. Now mind you, took the hubs and I 12 hours in a snowstorm during our pre-baby days. Took us 12 hours with two kids on a bright sunny day! Our road trip was wonderful as we stopped our Buick a couple times before reaching our destination. Be sure to stop by the Three Floyds Brewery during your drive and eat there too as you stock up on the beer! We navigated Chicago in a big group of six adults and 4 kids and while we did split up a couple times, for the most part we explored the Windy City as a troupe. We had our double stroller and I was surprised to see how stroller friendly the city is. We also took a few cabs as they were quite cheap compared to Toronto. Chicago has something for everyone, just like most major cities. However Chicago wins my heart with the great architecture and gorgeous water views right in the heard of their downtown.

 

 

Where to Stay

Chicago has many hotels and while we originally wanted to rent an apartment, we found it challenging to find one in a safe location at the centre of it all. Which is why we were absolutely thrilled with the location of our hotel, The InterContinental Chicago. As the only hotel actually on Magnificent Mile, this is a great spot to not only be at the centre of it all, but also a hotel with a lot of history that will please architecture buffs. For our full review, click here.

 

 

Where to Dine 

I had high hopes for dining out at numerous spots but the reality is that walk-ins with a group our size was pretty much impossible and we weren’t ready to wait two hours for dinner. So what you see below is where we got in to during our random pop ins.

Weber Grill : We ended up here out of sheer desperation once we couldn’t get into other spots late on Thursday night. Steaks were done well and service was good. The kids were exhausted and Little Monkey had tantrum after tantrum but luckily no one cared. They were kind enough to bring me hot water to warm the milk bottles too!

Giordano’s : Honestly I’m not a fan of deep dish pizza and if you’ve had it once, you’re probably good for life. Which is why when we ended up here I ordered wings. I did have a slice of deep dish to confirm that it really was as overrated as I remembered; My opinion stands. Giordanos was very kid friendly though (high chairs, change tables and plastic cups) and if you plan to order a deep dish pizza, be sure to come in early and place the order before going for a walk. Takes 45 minutes to get that pizza made!

Las Palmas : Stumbled here accidentally and was the best meal we had on our trip. I hope to visit again for authentic Mexican fare in a very kid friendly environment. Click here for a full review.

Ann Sathers : My friend chose this as our final meal in Chicago and said that this is where the locals go for a good breakfast. Reservations were made but we still had to wait 35 minutes to get in. Once in, food came by quickly and the eggs benny was good. Frech toast was ginormous and their famous cinnamon rolls are famous for a reason. Our server spilled some drinks on me and made it up to me for the rest of our meal…I felt sorry for the fella! He was too kind to us and some of those rolls even made it back to Toronto!

I plan to return to Chicago to explore the famous food scene and some spots on my hit list are : Purple Pig, Reza , Cafe Baba Reeba, Macku Sushi, Howells & Hood.

 

 

Where to Play

Chicago has something for everyone, from museums to play grounds, everyone of all ages will find something to do in Chicago. Something that will keep their heart beating and their faces smiling. It was hard choosing which spots we’d visit because my list was very long and even though I got a Chicago CityPass but wasn’t able to make full use of it. Quite a few spots remain for our next visit.

360 CHICAGO & TILT : To get a full view of Chicago and TILT out on to Mag Mile get yourself to the 94th floor of the John Hancock building. The kids were able to run around as it wasn’t busy and we got some amazing pictures up there. For a full review click here.

Chicago Children’s Museum : Our love for Children’s Museums continue and we were thrilled we got the chance to visit the one in Chicago. From driving a fire truck to digging dinosaur bones the kids and dads were entertained. Click here for a full review. If time permits you should plan to spend the day at the Navy Pier as it looks like fun, unfortunately we didn’t have time to do that.

Shoreline Sightseeing : The highlight of our trip was the architecture cruise we took and the fireworks we ended with. Definitely a must do during your first Chicago visit. Especially if you like to learn about the history of the gorgeous buildings. For a full review click here.

Millennium Park & Cloud Gate : Of course no visit to Chicago is complete without a visit to the famous “bean”. We goofed around as the kids slept and then hung out at the park and let the Little Monkey run around. This is a perfect stop half way through the day as kids can run around freely without a care in the world (for the parents).

Shed Aquarium : We made a quick visit to check out the penguins, the 4D Ice Age show and of course see the jellies. The space is stroller friendly but ask for directions because there’s various elevators for each wing and they can be hard to find. Plenty of stroller parking at each exhibit as well.

Wrigley Field Tour : We enjoyed our tour as we celebrated 100 years of Wrigley Field. Baby wear if you have an infant and definitely check it out if you’re a baseball fan. Click here for a full review.

 

Chicago can be an expensive city, especially when it comes to accommodations. We didn’t realize this but we visited during a busy weekend and so if you have the chance, plan your visit by checking Chicago’s city calendar. Avoid any big conventions and you’ll have better luck with the hotels. As you can clearly see we plan to visit Chicago again, hopefully sooner rather than later. Especially for the craft beer scene. There’s so much more to see and EAT in this city that I hope to get the full scoop for you!