Chicago with Kid{s}

Travel. Something we as a duo have always loved. It almost defined us for awhile, always looking for an adventure whether near or far. It personally gives me life to go to new places and have new experiences. To see how other people live. To breathe in a new culture. It was always a romantic notion that I would be able to do this with my little one in tow, and the time had finally come. We had decided to put on the training wheels and take her somewhere that wasn’t too far, that we had traveled to a few times already and that was kid friendly. We ultimately decided on Chicago.

Luna shocked us with her stellar behavior on the plane. I packed her a small backpack with some new toys and activity books (all from the Dollar Store), along with her tablet loaded with her favorite movies and some headphones. I also brought some lollipops to help with the change in pressure during take off and landing. Even with connecting flights, turbulence and no service or bathroom access, she didn’t complain once. We had prepared her a couple of weeks before with these awesome books that I found on Amazon. She knew what to expect, and I think that eased her anxiety.

We stayed at StayPineapple at The Alise, which was SUCH a lovely hotel. It was super central, in The Loop, which is very important when you have a little one in tow. They also have an amazing restaurant and bar (The Atwood), which was great after long days where we were too tired (or the weather was too bad) to look for one to visit. I think Luna loved the hotel more than the city, and would ask to go back to it all the time! She especially loved opening the huge windows and watching the busy city in the morning.

One important lesson we learned was that we cannot travel the same way we used to. It may seem obvious, but our kid is pretty good (as far as 3 year olds go anyways), and is used to our lifestyle, so we thought we could carry on in a new city. Not the case. She found some things to be the actual worst (like Navy Pier, especially when she saw all the fun amusement park rides were shut down or shopping down the Magnificent Mile), would get overtired or overstimulated, and it would result in the most psychotic of tantrums. She doesn’t tend to make these scenes in public so it led to some frustrating and embarrassing moments. Sometimes we had to walk a very long way, only to walk a very long way right back because she was not having it. We had a very loose daily itinerary and didn’t stress when we couldn’t do something or had to leave early. This is so important.

The days that “looked” more like the ones we have at home were the most successful. We catered to her and then squeezed moments to cater to us when she was napping. We were even able to have a grown up dinner at a hot spot at her bedtime as she slept in the stroller next to us. Looking back, although some moments were frustrating, exhausting or embarrassing, she did AMAZING for her first time and we were able to make some notes for future trips.

Here’s what we did and how we managed to do it!
I hope it helps all other parents that may be reading and wanting to explore a city with little ones in tow.

Friday

• flew in on a direct flight, hopped on The L and made our way to the hotel
• checked in, changed, and walked over to our lunch reservation at Cindy’s Rooftop. Luna fell asleep on the 5 minute walk over and allowed us to enjoy our food and several rounds of drinks before waking up. Gorgeous views, amazing food. Can’t recommend this place enough.
• went to Millennium Park, visited The Bean, had her run around and have fun.
• met a friend at Willis Tower and SkyDeck, explored the beautiful views, skipped out on taking photos on the “ledges” because they were 30 minute waits.
• walked to dinner at Small Cheval. The most ridiculously simple menu, but the most ridiculously amazing burgers ever.

Saturday

• Went to both The Field Museum + Shedd Aquarium back to back with friends and their son. Luna is obsessed with dinosaurs so the big draw for us was “The Sue Experience.” Totally worth it as dinosaur lovers ourselves. Big, beautiful museum that would take days to fully enjoy. Shedd is equally beautiful, but we missed some shows because Luna fell asleep while we were here. The winners for me were the arctic creatures since we don’t have them at home, like the penguins and beluga whales. They also had great play areas that Luna just loved.
• Hung out for a bit afterwards on an area between the Shedd + the Adler Planetarium with the most beautiful views of the city where the kids played.
• Returned to the hotel to have some drinks with our friends and the kids.

Sunday

• Went to Longman + Eagle in Logan Square for KILLER brunch. Very family friendly. Another gem.
• Went to a nearby shop, Wolf Bait + B-girls, and did some shopping. Really great place for local makers.
• Found a park nearby and had Luna play while we relaxed until the weather got a little dicey.
• Went to an Italian shaved ice joint in the neighborhood, Miko’s.
• Luna napped in her stroller while we visited Revolution Brewing + The Radler. Both really great places that we enjoyed.
• Did some more shopping at Logan Square when Luna woke up and then headed back to our neck of the woods.
• Went back to the Loop and had her run around Millennium Park some more before the downpour started….
• Had reservations for dinner at The Girl + The Goat right at her bedtime. She fell asleep just as our food arrived. AMAZING experience with delicious food and probably the best service I’ve ever had while dining.

Monday

• Breakfast at Yolk (local haunt that never disappoints)
• Walked to the Magnificent Mile to shop, went to Disney store (duh).
• Walked to Navy Pier. Luna was extremely unimpressed. Walked all the way back to Eataly (she fell asleep as we walked over). Really big Italian food hall with anything you can imagine. Snagged some pink bubbles and pizza.
• Made our way back to the airport.

I highly recommend getting the Citypass if you are visiting Chicago with kids because we saved a lot of money for admission into the big “tourist spots.” We even got priority entry for some. Also make sure to make reservations for the hotter spots weeks in advance because otherwise you will have to wait. A long time.

 

I hope this post was of some help to you all!
Have you traveled to a big city with your kiddos? Do you have any additional tips to share?
Arizona is next in September for us!