We are two and a half years into this pandemic, and travel is finally feeling more normal again.
I was nervous about flight delays and missing baggage being common nowadays but thankfully we didn’t have any of that. I think it helped to have an early flight because there were less people and less delayed flights before us. Adding AirTags to our luggage also helped.
This was my first time traveling by plane since the pandemic started, and my daughter’s first time ever on a plane. She was just a newborn when everything got shut down, and our travel plans for her first birthday (Turks and Caicos) ended up being cancelled. I was as excited as I was nervous about how flying with her for the first time would go. It definitely went better than I expected and I’ll share what worked for us in making it all go smoother.
We were in Chicago for a total of 4 days. The main reason we were going is for Lollapalooza, so we set aside one full day to see as much of Chicago as we could.
DAY 1
Boarding was at 4:30am so I left home to go to the airport with barely any sleep. Thankfully the little one slept longer which helped all of us. Happy baby, happy plane.
Our layover was in Vegas so our first flight only took an hour! I thought of booking direct flights at first but it ended up better to have shorter flights with layovers. Also I paid extra for early check-in, and we already had family boarding (priority boarding when traveling with a small child) so maybe it wasn’t really needed.
I packed a bag full of snacks and toys. The one she used the most was an activity book we got from Barnes and Noble, full of over 1000 stickers of Disney characters. She also played with fidget toys for a while, her favorite being a pink stretchy caterpillar that we got from the Target dollar section. Another Target dollar section find was Cocomelon play dough, which kept her amused way longer than I expected. It seems that sensory toys in general are best to take along. We also got “Wikki Stix” that she wasn’t as interested in, but might be an option if your kid is. Other toys I packed include Tegu magnetic blocks (their smallest set is perfectly travel sized), a small stuffed animal, and a matching card game from a Lovevery toy kit.
As a plan B, we also brought along an Amazon Fire tablet and downloaded offline games into it. Her favorite app is the PBS Kids Games since there are a ton of mini games you can pick from (we downloaded mostly the Sesame Street ones). She also played the Dentist game and the Doodle game for a while.
I had some kids shows/movies downloaded too as a plan C. Disney Plus and HBO Max had the best parental locks for a kids profile, while Netflix had no lock, and Hulu had no option of watching offline. Our plane had WiFi for watching free movies on a web browser but I couldn’t use it for other apps… it’s useful to check this ahead of time. I wanted to hold off on giving the tablet because once it was on, it can be hard to turn off without a meltdown at this age. At least it kept her busy while we spent the rest of the day waiting for the rental car… more on that in a bit.
Her ears hurt during takeoff and landing, so I made sure to offer a snack with water at those times. It also helped that we brought along her car seat (she sat on it on top of her plane seat). Even though it wasn’t convenient or easy to bring along, I think it was worth it to make her feel more secure. For reference we brought the Diono Radian and the travel bag made for it.
We landed around noon local time in Chicago and our car rental reservation was at 1pm so we went there right after. The place was packed with people not getting their car reservations and I spent hours standing in line to keep my spot. We were told to keep waiting and didn’t get the car until 5pm. Thankfully I packed food for the little one because at this point, it was past 12 hours since we got on the plane and I was starving.
We went straight to the hotel after getting the car because we needed to check in. It was outside the city, so we didn’t get in our room till around 6pm… the place we stayed at was another nightmare.
There were so many issues, from bugs to dirty linens to other things reminiscent of AHS: Hotel. The room was so tiny and so dirty. Even our toilet was messed up from the start, and we were told to wait while they sent someone to fix it. Two hours later, we told them we were going out for dinner and they could go into the room while we were out. They didn’t even try to fix it all night so in hindsight we should have left sooner for food.
We drove back to the city and spent the rest of the night at Navy Pier. Lots of food options to pick from, and on Saturdays they have fireworks too. That was really nice. We finally got to eat a little after 9pm, and decided to try Chicago-style hotdogs. The longest line was for Giordano’s (a franchise serving deep dish pizza) and thinking back I should have tried that too. We paid about $40 for parking a car, but if I came back I’d go during the day instead, possibly taking the bus/metro and walking. It was worth a visit though. Needless to say, Navy Pier was the highlight of our first day.
I couldn’t sleep at all that night because of how uncomfortable and dirty the room was. Thankfully we got clean (enough) sheets for the little one and she was able to fall asleep on the way back. We already prepaid for 4 days but it felt necessary to book another one for the rest of our stay.
DAY 2
Luckily after that first 24 hours, our trip got better! I was running on no sleep but I was hopeful for the new hotel. Got ready and wore our matching outfits. Stopped by Magnificent Mile so I could check us in, and we were finally headed to Lolla!
We had a stroller with us so walking into the festival was quicker than I expected! We waited in the Hulu popup line for a few hours, which in retrospect wasn’t too bad because it kept us mostly in the shade while the sun was out. Either way, make sure to stay hydrated! After, we made our way to the kids area called Kidzapalooza. My daughter got her first (airbrushed) tattoo and took some pictures before the kids section closed at 6pm. We even got to meet another mom and her son who was also an ARMY (BTS fan). It was so cute hearing him and my daughter talk about their favorites. After, we walked around the rest of the festival grounds and checked out all of the stages, then got some food before making our way back to the Bud Light stage near the entrance.
It was perfect timing. Around 9pm J-Hope (a member of BTS) was headlining and performing his solo album for the first time! We got there right before and laid a blanket down to watch. There was a lot of people near the front, so we stayed in the back just in case to keep the toddler safe. She was waving the light stick as if she was right in front of the stage. Also it was only 7pm in our usual time zone so she was wide awake and not cranky (adding this because people asked). Definitely helps to plan out schedules ahead of time when traveling with a kid.
We were happy to just be there in person. J-Hope is an amazing performer and that by itself was already worth the trip! As we were walking back to the car, we happened to see J-Hope and Jimin (another BTS member) on the other side of the gate leaving at the same time.
DAY 3
Sightseeing day!
After eating we made our way to Skydeck Chicago. It’s a glass balcony on top of the Willis Tower, offering amazing views of Chicago. It wasn’t as scary as I thought it would be! And my toddler was absolutely fearless, stepping out on the ledge and looking 103 floors down like it was nothing. You get to learn a bit about Chicago’s history as you make your way to the top and cute photo ops too, like a life-sized deep dish pizza you can lay down on! We got tickets ahead of time which I highly recommend; it was still busy on a Monday.
We got a bus pass for the day. It was great to explore and to avoid paying for parking at multiple places throughout the city. Public transportation seemed cleaner and fairly easy to take compared to Los Angeles. The only thing was that the schedule was inconsistent… we had 3 buses that didn’t show up at all towards the end of the day. So we ended up walking back to the hotel which luckily wasn’t too far from where we were at.
I only got the rental car for the trip because we originally planned to stay outside of the city, but if I could do it over, I would book a hotel in the city from the beginning and avoid a rental altogether. Also check if there’s a valet fee (per day) to park your car at the hotel if you do have one.
So back to the itinerary! It was a quick ride from Skydeck to the Bean aka The Cloud Gate. We walked around Millennium Park (there was a concert!) and Maggie Daley Park, where there is a ton of kids play areas. My daughter loved it there! This easily could take up your entire day, but we only stayed about an hour so we could leave around sunset.
We walked along the Chicago Riverwalk as we made our way back to the hotel. The last stop on the itinerary was a (free) nighttime Art show display at The Merchandise Mart, but we were exhausted at that point so we decided to skip it.
Instead we walked to get pizza near the hotel. Keep in mind that deep dish pizzas usually take at least an hour to make, so if I did it over I would just have gotten it delivered lol. The little one fell asleep in her stroller and was able to sleep through the night—running around that park definitely helped!
DAY 4
Our hotel came with free breakfast, so we went down to eat before checking out. Afterwards we drove around Magnificent Mile. We walked around the area the night before, but it was different during the day. It was nice seeing the stores open too!
For lunch we ate at Nutella Cafe. It’s located in The Loop, where we were the day before. Everything at the cafe was so delicious! We tried the Nutella croissant, Nutella waffle with hazelnuts and Nutella whipped cream, a double scoop of Nutella gelato, a Nutella popsicle, and Nutella creme brûlée. The Nutella biscuits were my favorite (should have gotten some to go!) but everything was really good. We waited about half an hour on a weekday.
After that we stopped by for some last minute shopping. We checked out the American Girl store and the Lego store next to it in the mall. My daughter got Gwynn, her first American Girl doll.
We headed to the airport after to return the rental and to check a bag with the stroller. I confirmed that everything was good with the car (made sure to return it at the same time we got it) and they assured me there wouldn’t be any extra charges. Surprise, surprise. They double charged me afterwards and now (two weeks later) I’m still disputing it with my credit card company. Lesson learned: don’t book a car with Budget. Anyway.
We had a layover in Denver so we didn’t get home until about 2 in the morning. My daughter played mostly with the activity/sticker book and the tablet on the plane rides home. I did have to hold her on the last flight when her ear was hurting but other than that, everything went really well and much better than I hoped. She loves flying now and is ready to travel more!
A few notes for making TSA checks easier. I packed the formula stuff (formula bottles, formula cans, bottle brush, and two water bottles) in a separate bag so it was easy for them to set aside and look over. There’s no limit on formula and baby food as those are considered medically necessary. I did email Lollapalooza ahead of time about formula and had her prescription ready to show. Be ready to take it out and be ready to take out the tablet if you bring one.
Also no limits on meds as long as you mark it separately; I put in a separate labeled quart-sized ziplock. Meds for her that I packed include Maty’s all natural baby chest rub, Genexa kids’ tummy relief, children’s Zyrtec, FeverFrida cool pads, colorful band aids, first aid/burn cream, alcohol prep pads, hydrocortisone cream (for bug bites), and a Bugables citronella bracelet. For myself I also packed Earplanes plugs, Dramamine tablets, TUMS, Advil, lavender balm for my migraine, and cough drops. That last one helped a lot because the dry air in the plane was bothering my throat.
Back home it helps to have Covid tests ready too. I tested after coming home and 5 days after our last time on the plane just to be safe. We are vaccinated (even the little one) and wore a mask most of the time we were on the plane. It seemed to help because I know so many that got sick on the trip (we didn’t end up being able to meet up with them in person though) and thankfully we made it through everything okay. I also brought vitamins and elderberry during the trip for an immune boost. Probably not all necessary but I was just trying to be extra cautious.
Other useful things to pack are headphones, sunscreen, dry shampoo, lotion, etc. Also packing dish soap for the little one’s bottles and cups helped a lot.
Check out my Insta to see what beauty items I packed! I brought along travel-sized skincare and haircare in a ziplock. For makeup I separated my liquid foundation, setting spray, brow gel, mascara, and liquid eyeliner into a ziplock.
Summary of sights we saw: Navy Pier, Skydeck/Willis Tower, The Loop: Cloud Gate/Millennium Park & Maggie Daley Park & Nutella Cafe, Magnificent Mile: American Girl store & other shopping.
Have you been to Chicago and is there anything you’d like to add? Did you take a summer trip, and are there any trips that you have planned?
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