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It has been a long, long time since I wrote a travel post. Travel content, including travel guides and travel tips, used to be my very favorite thing to write. The last one I put together was a compilation of links to all my posts about our 2.5 month long backpacking trip in Europe, and I posted that in January 2018. So, after a long hiatus, I am back with more travel content. The next several posts I share will be focused on traveling with a baby, but this post in particular could be used by someone traveling sans children.
Today I am sharing about our family trip to Chicago during July 2018. This was my baby boy’s first time on an airplane, and he turned 3 months old while we were on this trip. I have lots of content on flying with/traveling with babies coming soon, so that won’t be the focus of this post. Today I am sharing what we did in Chicago for baby’s first big trip. And, even though we were “newbies” to traveling with a little one, we came home from that trip feeling like we made the most of our time in the Windy City, so I feel comfortable sharing this post as a guide to enjoying a trip to Chicago with a baby. I have also shared a map outlining our trip at the bottom of this post.
The Trip
Our time in Chicago during July 2018 was part family vacation and part web development conference for my husband Daniel. Since I was in the middle of maternity leave, it was the perfect time for Baby Carson and I to tag along. We were so excited but so nervous about our first big trip with Carson. We flew in on a Saturday, and we had through Tuesday to enjoy Chicago together as a family. Then Tuesday through Thursday Daniel had his conference while Carson and I hung out and took it easy. We flew home Friday.
The Flight
Again, I’ll be sharing more practical information based on what I learned flying with my three-month-old in a future post, but I had to document Carson’s first flight here! He did great and slept like a dream in his DockaTot. For a baby that didn’t nap very well at this age, we were pleased to have a flight filled with snoozes and smiles. Even the airport experience itself (checking in, getting through security, boarding the plane, etc.) went just fine.
Transportation in the City
One of my concerns when planning this trip was how we were going to get around with a baby. In the recent past, we did take a lot of public transportation, but we could also easily call a Lyft or Uber which we were now unable to do since we would have needed a carseat. However, using the Chicago public transportation system was no problem for us at all. You will see below in Day 1 that we opted for a private transfer to and from the airport because we had a lot of luggage, but the rest of the time we either walked, rode the Metra rail system, or rode buses. I discuss some of this more below, but in the end, it was very easy to use public transit, even with a full diaper bag and an infant in a stroller.
The Itinerary
Some of you may look at the title of this section and laugh. Really, an itinerary with a baby? Well, I have to say, especially at this age when they are so small, it really is possible to have an itinerary, albeit very loose and flexible. That being said, here is what we did each day during the trip.
Day 1
Our flight, getting to the hotel, settling in, picking up our pre-ordered Amazon Primed diapers and wipes from the front desk, and running to the store made up all of day one. In this photo, Carson is in an infant carseat that was provided by our car pick-up service with Ride in Bliss. We decided to splurge on a private car service for Carson’s first big trip primarily because (a) we had a lot of stuff for our week in Chicago with an infant, and (b) we wanted to make this first trip as easy as possible because we were so nervous when planning! We are glad we made this decision as it definitely made our first and last days of the trip more relaxing.
The Hotel
We chose to stay at the Hyatt Place Chicago/River North because of its proximity to places we wanted to walk, access to a train station, and our ability to use Hyatt points to book the room for part of our stay.
The hotel had the standard hotel pack ‘n play, and it even had a sound machine in the room already. We also had a wonderful view from our window. It was great for our five night stay with our baby.
In the earlier days of traveling with Carson, we opted to let him sleep in his Dockatot inside of the pack ‘n play since he was used to sleeping in a snug bassinet at home, and it gave us peace of mind that he would not be flipping over onto his stomach or pushing his face into the side of the bassinet while we were all asleep.
Day 2
Morning Walk
The second day began with a walk around the city. We just love Chicago. I’ve been many times in conjunction with work trainings, and I blogged here about the last time Daniel and I were there together in 2014. One of my favorite things about Chicago is the beautiful architecture mixed with the Chicago River and the energetic vibes of the city, so I was sure to soak all of that in during our walk.
As you can see, it was a foggy day! But still beautiful nonetheless….
One funny side note: we saw our stroller brand, UppaBaby, ALL OVER the city. I know it’s a popular stroller brand, but of all the places we’ve traveled to date since having Carson, I have never seen so many UppaBaby strollers being pushed around. Our stroller was perfect for strolling around Chicago so I recommend it for those of you parents who are considering stroller options for city walks.
Monteverde
Our morning walk ended at Monteverde, an Italian restaurant in the West Loop. We met my friend Suramya who lives in the city there for brunch. It was so good to see her and for her to meet Carson! Unfortunately, Carson left a surprise for her in the form of his first blowout while she held him. Thank goodness, she has a little niece and nephew and loves babies! Of course his first big blowout ever would be in a nice restaurant on my friend wearing a white shirt! Anyway, Monteverde was a great option for a nice brunch in the West Loop, even with a baby. There were several families with kids there, and they let us push the stroller next to the table, so it’s definitely family-friendly (at least for brunch). Definitely make a reservation though – the place is popular!
After brunch, we walked back to the hotel for naps and showers. While it was much cooler in Chicago than at home in Austin at this time, we were still sweaty by the time we got back from our walk.
Lou Malnati’s
That evening, we checked another thing off our Chicago “to-do” list and went to my favorite deep dish spot – Lou Malnati’s! I didn’t take any photos of the food that evening because our hands were full passing Carson back and forth while eating our food in between. In my opinion, Lou Malnati’s is certainly the best deep dish in Chicago. You need it on your Chicago itinerary! There are locations all over the city. This one was just a few blocks from our hotel.
Day 3
Caffe Umbria
After an early wake-up and a feeding session, we were ready for some good coffee. We love trying new coffee shops when traveling, so this trip was no exception.
That morning, we shared a Chemex at Caffe Umbria. The cafe itself was completely packed, so we sat in the overflow seating in the lobby of the connecting building where there was plenty of room for our stroller and to pass the baby back and forth between coffee sips. The coffee was delicious!
Lincoln Park Zoo
Next on the agenda was Carson’s first trip to the zoo! I had never gone to Lincoln Park Zoo before, and it seemed like the perfect opportunity to go during Carson’s first big trip. We took the bus over from Caffe Umbria, which was a surprisingly easy thing to do with a baby in a stroller. Because the bus was not full, we were able to keep Carson in the stroller in the spot with the fold-up seats and stand there with them. The bus took us straight to the entrance of the zoo with no problem at all.
We spent a wonderful morning at the zoo, stopping for lots of breaks and feeding sessions while staring at the animals. My favorite (and I think Carson’s favorite too!) was the gorilla exhibit.
Directly outside of the zoo, there is a nice garden area with lots of shaded benches. We took another break there after spending lots of time looking at the animals in the zoo.
The Wiener’s Circle
After our break, we walked over to The Wiener’s Circle hot dog stand to check another must-do off of our Chicago list. Our Chicago dogs were yummy, and they thankfully had a few tables outside so that we could rest our feet.
After lunch, we went back to the zoo to see a few more animal exhibits.
Ramen-San
One of our favorite types of foods to try in different locations (other than the local cuisine) is ramen. So, when we saw that our hotel was right by a ramen place, we knew we needed to go! We each got a bowl of ramen, and we shared the pork buns. We used to live across the street from the original Ramen Tatsu-ya in Austin, so we are always comparing other ramen places to that one. Ramen-San was good, but I would not say it was anywhere close to the wonderful-ness that is Ramen Tatsu-ya.
Day 4
Day 4 was our final day together with Daniel, so we were ready to make the most of it.
Intelligentsia Coffee
Again, we started out the morning with some delicious coffee! Intelligentsia is know as one of the original “Big Three” third-wave coffee shops in the US, so while they have grown tremendously, they still serve wonderful coffee. We got a pastry as well. Carson was content in his stroller next to us which made this coffee shop visit all the more pleasant.
There are many locations for Intelligentsia, but we went to the Millennium Park location since our next stop was The Bean.
Millennium Park
The Bean at Millennium Park is a must-do attraction at the top of most Chicago tourists’ lists. We had been before, but I wanted to take Carson. Parks are a great place to take babies while traveling because the babies can either snooze or sit in their stroller, or you can take them out and let them people watch while sitting on a bench or in the nice grass.
After a quick, sweaty photo shoot by The Bean (there was no shade over there!), we scouted out a shady spot to sit and do our three month photo shoot.
Behind the Scenes of a Newborn Photo Session:
The Final Result:
Carson was a very happy baby people watching in the shade!
Goddess and the Baker
Next we walked to Goddess and the Baker for a relatively healthy and highly Yelp-rated lunch stop. We loved our salads and drinks (juice for me, an iced latte for Daniel), and Carson loved doing some more people watching. There wasn’t room for our stroller, but it was easy enough to fold up and put to the side while we ate.
On Tour Brewing
We then made our way to On Tour Brewing, but we took the long way! We took the Metra from lunch to the brewery, but before we got there, we went the opposite direction on the Metra for THIRTY MINUTES. We blame the fact that there are two Metra stops on the same line with a very similar name, but it was probably just “mom and dad of an infant brain”. We were glad that Carson chose this time to nap or else he probably would have gotten a bit impatient.
Once we arrived at the brewery, we enjoyed sitting in the air conditioning sipping a few samplers. The brewery was great and had lots of space – we recommend it!
Forbidden Root Restaurant & Brewery
We ended this day with dinner at another brewery, Forbidden Root. The restaurant here was much nicer than we expected, but the food was wonderful. We shared a roasted chicken plate and a cheese plate for dinner. Yum!
Days 5 and 6
On days 5 and 6, Daniel spent all day at his conference, so Carson and I spent these days mostly alone together. These were the toughest days because Carson would not nap for more than twenty minutes. I remember trying to write this blog post (over one year ago!) but not being able to because he wouldn’t sleep. While they were hard, they were also sweet days because we spent lots of time playing and walking around the city together.
Ema
One evening, Suramya (who had met us for brunch a few days earlier) came to dinner at the hotel restaurant, Ema, which happened to be a really great Mediterranean small plate restaurant. There is an overflow section in the hotel lobby that had plenty for room for the stroller next to our table.
Lou Malnati’s (Take Two)
One afternoon I went and got myself a personal-sized deep dish pizza at Lou Malnati’s and took it with me for a walk. Once Carson finally fell asleep, I sat down and ate my pizza by the river.
Travel Home
Our flight home was just as successful as our flight to Chicago, but we did arrive home very ready to be back.
I hope that this post gives you some inspiration for your next trip to Chicago, with or without a baby. Even though we packed in a lot less than we would without Carson in tow, we certainly did more than I thought we’d be able to manage with him. This was the first of several trips we have taken with our baby, and I look forward to sharing more travel guides and tips & tricks in upcoming posts!
This article is now available as a mobile app. Go to GPSmyCity to download the app for GPS-assisted travel directions to the attractions featured in this article.
{Thanks for reading! Want to know a little more about me? I’m a CPA learning how to balance a career with motherhood and regular travel while planting roots at home in the Austin, TX area. When I’m not exploring my home city with my husband Daniel and baby boy Carson or cuddling with my chubby orange cat Banana, I’m probably either out on a playdate with my son or planning, packing for, traveling to, or daydreaming about our next adventure. After all, my travel mug collection is never complete. If you have wanderlust too, be sure to follow me on Instagram (and InstaStories!), Pinterest, and Facebook, or subscribe to my blog!}
Itinerary Map – Click the icon at the top left to see a list of the pinned locations by day.
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