I have so many post ideas I want to share, and this one topped the list. Mainly because everything’s still fresh on my mind!

Vishnu and I took the kids (Kaiden – 6 and Mila – almost 2) to Chicago a couple of weeks ago for a few days. We picked Chicago because it was home for five years and we wanted to share one of our favorite cities with the kids (spoiler alert – they loved it!) and because it’s a very family friendly city we’re (re: Vishnu) familiar with. We truly had the best time!

So let’s kick this off with my usual travel blog break up…

Where we stayed

Because we had the kids with us and could use the extra space, we rented a condo on Airbnb in the Gold Coast/Streeterville area. The unit itself was fine…a little dated but clean and good enough for us. The location, however, was perfect. We walked everywhere! There were coffee shops, restaurants, parks, etc. all within a few blocks of us. This is a great area to scope out, especially in the summer.

Where we ate

I wanted to take the kids to some of my favorite Chicago restaurants, but Vishnu quickly reminded me that we would never be welcomed back if we did that. So we opted for more family friendly places instead!

Wildberry Pancakes and Cafe – A must go to restaurant right off the Magnificent Mile (there are a few different locations around the city). This place has everything from oatmeal to pancakes to skillets to omelettes. The kids’ menu is extensive with options for even your pickiest eaters. We had breakfast here twice.

Cafecito – We had lunch with our parents here years ago so my expectations were super high. Cafecito has a Cuban inspired menu that sounds delicious. We liked what we ordered for breakfast, but didn’t love it the way we always do with Wildberry. Our food was a little oversalted and the coffee was nothing special.

Boca Loca Cantina – When we lived in Chicago, I always said the one thing the city was missing was a good Mexican restaurant. And now they have it! I loved this place in River North. They have a TexMex type menu with delicious options for everyone. My enchiladas were amazing, and I really enjoyed the spicy guac too!

Parlor Pizza – This is a really family friendly pizza place with plenty of outdoor seating. If I’m being honest, I’m not the biggest fan of deep dish pizza (what Chicago is known for), so I was really glad that Vishnu made reservations for Parlor. The pizza is unique – we had a burrata pizza that was to die for – and super delicious. Even the pepperoni pizza had something to it!

Protein Bar & Kitchen – The thing I love about Chicago is that there is some kind of cafe or restaurant literally everywhere. One of the days, we found ourselves walking back home and not super hungry, so we stopped at Protein Bar and picked up smoothies for everyone. Quick, delicious, and healthy.

What we did

I’m going to break this up by day so you can see our little itinerary. We based this off of Mila’s nap, and it worked well for us!

Evening of arrival

We dropped off our stuff at the condo and headed to our friends’ place for dinner (their son and Kaiden went to daycare together for 3.5 years!). The perfect way to kick off our trip!

Day 1 AM

Breakfast, park (across the street), Navy Pier (walk around, Ferris Wheel, Swings, and Carousel, lunch at the food court).

Break for nap, showers, and rest

Day 1 PM

Old neighborhood, park, meet up with Amy, dinner

Day 2 AM

Breakfast, Milienium Park (the (boring, per Kaiden!) Bean), Maggie Daley Park, lunch

Break for nap, showers, and rest

Day 2 PM

The Museum of Ice Cream (highly recommend) and dinner

Day of departure

Breakfast, park, airport, and home


We chose to rent a double stroller and a pack n’ play via BabyQuip. This was live saver in terms of not having to lug things through the airport. And the double stroller really helped save us from ALL THE from Kaiden. HIGHLY RECOMMEND!

And it goes without saying, but pack really really good walking shoes. Chicago is absolutely beautiful and magical in thee summer, and you will want to walk everywhere! We logged over 72k steps in under 4 day!

I think that’s the long and the short of our trip! Let me know if you have any questions!

By Parita

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