How to Travel in a Large City with Kids

Traveling with kids can be stressful, but it can also be one of the best ways to connect and create long lasting relationships and memories! Here are some tips on how to travel in a large city with kids so you can enjoy your stay to the fullest!

      1. Have a helper (spouse, parent, sibling…) If at all possible having an extra set of hands will make your travel so much more enjoyable. Tag teaming who looks up directions while other helps the baby or the bare necessities of carrying the luggage and getting in and out of buses/vehicles can be a huge help. If you do not have a helper, consider buying strollers that can carry a couple kids and have space for luggage too. Two of my favorites are the sit and stand, as it can hold a child and luggage pieces quite comfortably. My favorite side by side is the Britax double. It is a side by side, but it is still narrow enough to fit through a single size door. 
      2. Talk to your kids about safety (how to cross the street, cars, traffic, watch where you walk) If your child is younger or if this is their first time in a big city, they may not understand how quickly traffic can come through. Talk about a safe distance to stand back from subway cars, understanding the traffic signals and sounds of a busy street, or simply being aware of their surroundings. I like to do a buddy plan with my kids so that even though my eyes are looking out for them they are also looking out for each other.
      3. Talk to your kids about what to do if you get separated. Have your child memorize your name and number so that they can get help from a stranger if they get separated from you. If your child is too young to know your number you can buy them a wrist band with your name/number on it, or simply write your name in pen on their ARM. Hands tend to get washed and messy, so putting your number on their arm will make it an easier place to stay safe. Another good idea is to take a picture of your child at the beginning of each day so that you can identify them with what they are wearing that specific day, and an outfit that others can spot is so helpful too.
      4. Get a sturdy but small stroller. 
        You don’t have to buy the most expensive stroller to get a good one. My favorite brand are the city stroller and Britax.
      5. Research your transportation options (uber/taxi, you’ll need carseats, shuttles, buses and subway you won’t. but find out the ease of public transit in each city) I have traveled in areas where I simply brought the booster/carseat along with us as I transported a baby through Boston and New York City. I loved using this Britax stroller that could pop right into the stroller from the car seat.

        light weight travel options

      6. Always enter subways, buses and elevators adult, children and then another adult. Getting separated during transitions can be one of the most stressful times as well. Designate who will be the leader and who will follow up so you can keep eyes on the kids the whole time!
      7. Get kids’ attention before moving on or off shuttles, buses, elevators, subways or going in and out of buildings. Keep them in the loop of what’s happening or about to happen. Buses, elevators, and subways are almost always crowded and there have been times that we have been separated to find a seat for everyone. Try to make a plan and tell the kids what stop you’ll be listening for. Also, keep eye contact and let the kids know when it is time to get ready to go. Enlist your older children to help queue the younger ones too.
      8. Find a hotel with a shuttle. I love the service of Uber and Lyft, but sometimes using those services or public transportation can add up quickly. Oftentimes your hotel will offer shuttle services to popular travel locations or hotspots. You can also check on prices for hop on/hop off services or check to see if you have access to a CityPass that can take you all around town all week long.

    1. Check luggage at a hotel. Talk with your concierge to see if you can have your luggage checked and shipped before you ever get to the airport. This service has saved me so many times!
    2. Don’t over-schedule. I have made this mistake in the past and always regretted over scheduling my kids. I tend to be a “go getter” and wanting to see all the things, but this is exactly the thing that will send your kids into overdrive where meltdowns and tantrums will start happening. Take naps, take a break, sit in the shade and eat an ice cream cone. These slow moments may be their favorite times of the whole trip.
    3. Find places for kids to play and have downtime. No matter where we are visiting, my kids love having unstructured play time. This could mean a swim in the hotel, a picnic in the park, or tv time in the hotel room. 


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  1. Let go of the “foodie experience” you may want to experience all of the local favorite hot spots for food/drinks but if you’re traveling with kids chances are it may not be the best fit. If you’re dying to try out a certain menu item or experience pick one or order to go. 
  2. Do more activities in the morning and afternoon. No matter where you may be visiting you and your kids will always be freshest in the morning and in the afternoon after lunch and a break. The morning hours can also be one of the very best times to see different places because the crowds are down and you’ll have a much more enjoyable experience.
  3. Hotel pool for evening time (great way to unwind and get out of the city at night) City life can get a little crazy and uncertain at night. Bring the party in and enjoy a dip in the pool. A lot of times you can even find fun places nearby that will deliver to your hotel. My kids love having pizza of course, but there are other options that are delicious and deliverable too, check with the concierge as they will always tell you the best places to try.
  4. Be prepared (snacks, drinks, bottles, etc…) Nothing changes the atmosphere more than a bunch of hangry/thirsty kids (or husband if you know what I mean!) I love using a bottle that is refillable and having enough snacks to sustain you while you’re out and about. Dry snacks are the lightest to carry, but don’t forget to pack things that are a little more filling like nuts, protein bars, and dried fruits.
  5. Get a backpack diaper bag. I have fallen in LOVE with my Ryla back. It is the perfect size for a day out on the town. It has insulated pockets, separate zipper compartments, and frees up your hands to do whatever you need to do. It is also small enough that I could have my oldest son carry it and know it wouldn’t break his back. You can snag your own RYLA pack with this special discount code:MYMOMMYSTYLE FOR 15% off. I am obsessed with their new leather line, they are sleek, gorgeous, and so lovely.
  6. Be flexible. Plans will change. You may be delayed by the pace of your kids, or a tantrum, or a dirty diaper. Allow for room to wiggle so you make space for magical moments too.

I am taking my two oldest to Chicago in a couple weeks and I cannot wait to explore the city with them! We are going to see Hamilton and explore the sites while my husband is in a work conference. I cannot wait to share with them the wonderful city of Chicago, my husband and I loved traveling there. More on that trip to come soon!

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