City Love in Chicago: Celebrating Our Anniversary with a Baby in Tow

Your Go-To Travel Guide for Food, Fun, and Family-Friendly Spots in Chicago

One year down, forever to go! In true city-girl/boy fashion, we celebrated our one-year anniversary exploring the beautiful and [somewhat] busy streets of Chicago for three days. 

My husband is from New York and I lived there for five years [it’s where we met and started dating], so we’ve been craving a trip to a city that felt just as vibrant. It was my second [or third] trip to Chicago and his first, so I was a little nervous about how my New Yorker would enjoy his time here. Let’s just say he absolutely loved it! 

What made this trip even more special? Our 3-month-old baby girl was right there with us, making every moment sweeter. Here’s a look back at our unforgettable trip—a perfect blend of love, fun, and ahhhhmazing food.

Where We Stayed

The Residence Inn Chicago Downtown Magnificent Mile was our home for this trip, and it was such a great choice for our little family. We went with the 2 Queen Bed Studio, which was more than spacious enough to spread out (a must when you’ve got a baby and a ton of bags for all of their things). It was 500 sq ft [quite frankly probably bigger than my NY apartment] and had a beautiful bathroom, closet area, multiple seating areas, and a small dining table. The [beautifully designed] kitchenette had everything we needed—stovetop, dishwasher, fridge, microwave, sink—and was perfect for prepping and sanitizing our baby’s bottles and storing any food or snacks we may have needed. 

The hotel is right off of Michigan Ave., so plenty of shopping, eating and sightseeing nearby [it’s right next door to the Starbucks Reserve Roastery if that’s your thing]. Butttt, it’s tucked away enough off of the busy street to still have some peace and quiet when needed. Plus, it was only a short drive to some of the city’s best spots, but we actually ended up walking to most places just to soak up the city view and vibe.

Check out my recap of the hotel on my Instagram [@everydayyyytay]. 

What We Did

We kept things simple, but also fun, focusing on iconic Chicago experiences that worked for all of us. Here’s what made the cut:

• Chicago Architecture River Cruise: Hands down, the highlight of our trip. Gliding down the Chicago River while learning about the stunning architecture was magical. Boats, nice breeze, wine in hand, soaking in the history and views. We did the 45-minute 10am tour which was very family-friendly! We booked through @getyourguide @wendellaboats.

  
  

• Exploring the Riverwalk: Following the boat tour we decided to take a stroll along the Riverwalk. We also made it a point to walk through when visiting other parts of the city like West Loop [yes we walked to West Loop…I was overzealous, but we enjoyed the longer stroll lol]. Between the river, skyline views, and vibrant energy, it was the perfect place to just be and take in the city.

  
  

• Maggie Daley Park: If you’re visiting Chicago with kids, this park is a must. From imaginative play spaces to picturesque walking paths, it’s an absolute gem. Watching our little one’s face light up as we walked through was so sweet and it was nice to sit and take a break from all the walking we did. 

  
  

• Eat, Eat, EAT: Because let’s be honest, Chicago’s food scene deserves all the attention. More on that below.

Some other activities we didn’t get to, but you should totally consider are: Shedd Aquarium, Lincoln Park Zoo, Navy Pier [although we saw it on our boat tour], Garfield Park Conservatory, Chicago’s Children Museum, Griffin Museum of Science and Industry, Field Museum, Millenium Park, and Wrigley Field.

NOTE: We didn’t get to go to the Skydeck at Willis Tower, but I do want to take my husband the next time we visit [I went on one of my previous trips and loved it…although terrifying]. And we totally missed seeing The Bean due to getting turned around during one of our walks and totally forgetting that it was one of the landmarks we wanted to see!

Where We Ate

Chicago is a foodie’s paradise, and we made sure to sample as much as we could. Here’s where we indulged:

• Roister: Modern, creative dishes served in a cozy, intimate setting. We went for brunch and it did not disappoint! They are known for their chicken so we definitely ordered the fried chicken and waffles, fried chicken sandwich, potato wedges and some really great cocktails! [Note: as of the publishing of this blog post, Roister is temporarily closed. They are exploring future opportunities and locations for the concept. FIRE by The Alinea Group will be replacing its location]. 

  
  

• Etta (Bucktown): We loved this charming neighborhood spot—it was probably our favorite of the trip! The food was flavorful, and the ambiance was laid-back yet refined. I believe their menu is seasonal, but we ordered the bubbling shrimp, hearth wood fired branzino, charred broccoli, robuchon style whipped potatoes & tres leches cake. The drinks were also so good [I remember having such a great matcha cocktail]. 

  
  

• Au Cheval: Can confirm: their burgers are worth the hype. Single cheeseburger w/ thick cut bacon [it’s really a double burger]. Add the crispy fries, and you’ve got yourself a meal to remember! I can’t resist a caesar salad anywhere I go [especially a kale one] so we ordered that too along with some yummy bourbon espresso martinis to top it off.

  
  

• Aba: We went for happy hour and got to sit on their beautiful rooftop patio. Loved the small plates to share like the crispy halloumi & spicy chicken wings. We may or may not have had 4 or so [each] of their cadillac margaritas and tried the “Aloe? It’s Me.” 

  
  

• Giordano's Pizza: I mean…it’s Chicago, so deep-dish pizza was a must. Crispy calamari and thick, cheesy pizza loaded with toppings—we were full for the remainder of the day! 

  
  

• Alla Vita: Italian comfort food done right. It was the perfect way to wind down after a long day of exploring. Another day, another kale caesar salad [shocker]! Also got the rigatoni, grilled oyster mushrooms & pumpkin spice cake. Yum, yum and YUM!

All of these spots were super baby friendly! We just made sure to put in a note when we booked our reservations to ensure we had space for her stroller. Everyone was super accommodating and so sweet. 

Final Thoughts

What a blessing this trip was! Celebrating one year of marriage in a city as vibrant as Chicago, with our little one along for the ride, felt so special. I was super nervous as it was baby's first trip/airplane ride and she did sooooooo good y'all [to the point where people didn't even know she was there half of the time because she was so quiet]!

I can’t recommend Chicago enough! It’s super walkable, beautiful scenery and clean, tons of parks, SO much to do for families, great food, nice people, and the list goes on.

We’re grateful for every laugh, every bite, and every moment spent together here. Chicago, thank you for the memories! It was great to experience one of my favorite cities with my favorite people. Here's to many more anniversaries, adventures, and milestones to come...[and maybe longer stays....*wink*]

Tip: I would suggest going during less busy times as we did [like a Sunday to Wednesday] to avoid the super busy crowds and being able to move at your leisure.

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If you’re planning travel with your family soon, check out these baby travel essentials that are sure to make your trip a little easier!

And, don’t forget to save this post to serve as your Chicago family [or friend, date, or solo] travel guide!