5 Fun Cities to Explore With Kids

If you follow along on our adventures, then you already know that we love to explore the outdoors and hike around National Parks. But, we also enjoy changing it up sometimes and venturing to the city with our boys. Below are 5 fun cities to explore with kids!

5 Fun Cities to Explore with Kids: DC, New York City, Philadelphia, Chicago, and Dallas!

Washington, DC

Touring the White House was on my bucket list for years!

Washington, DC was the first big city we traveled to with our kids. It was such a great “starter city” for our family. Not only is it extremely walkable, there’s so much to do. And the best part is, there are several free activities around the city to enjoy!

The boys’ first request was a visit to the Lincoln Memorial!

We’ve traveled to DC in September, November, and March. We got lucky on all of our trips and had gorgeous weather each time. DC is stunning in the fall, but just as beautiful in the spring with the cherry blossoms in bloom!

My littlest boy, cherry blossoms, and the Capital!

My favorite visit was our trip over our Thanksgiving break in November. The city was not crowded at all, which made it easy to explore the museums and we didn’t have to wait long for dining at restaurants. The only downside is that we were not able to tour the White House because it is closed this week for Christmas decorating.

Excited to be in DC!

Washington, DC Must Dos:

We can say we’ve been inside George Washington’s house! It was beyond amazing!

Be prepared for a lot of walking. We clocked an average of ten miles per day when we were there! Our boys were only five and nine on our first visit and were tired, but made it just fine! We did use a taxi to get from the airport to our hotel. There are also several taxis that stay around the National Mall area, mostly near the Lincoln Memorial. We jumped in a few of those when the boys were too tired to make the walk back to the hotel for the night.

Posing with the White House

Our most memorable moments of our trips to DC were going inside the White House, watching President Trump leave the White House on Marine One, seeing George Washington’s actual teeth on display at Mount Vernon, and seeing the original United States’ flag & the Declaration of Independence!

George Washington’s actual teeth on display at Mount Vernon!

Click here for my tips on securing a White House tour.

Click here for my complete Washington DC guide.

New York City

Top of the Rock

New York City is an amazing destination for just about anyone! I’ve traveled to the Big Apple with my boys twice now and honestly, we can’t wait to go back!

Our first visit to the Statue of Liberty!

We’ve visited NYC in June and in November. Summertime can get pretty hot, but we’re from Texas, so we’re used to it. Our first day in the city on our November visit was extremely cold, but the rest of the days felt really nice.

My favorite, Christmastime in NYC!

I loved both visits, but there’s something really special about traveling to this city before Christmas! We enjoyed the Christmas décor so much. So, I have to say that our trip over Thanksgiving break in November was my favorite. I highly recommend visiting this week if you can! We got to see the Macy’s Thanksgiving Day Parade and experience all of the Christmas spirit at the same time!

The Empire State Building!

New York City Must Dos:

Summer in Central Park!

You should also prepare to walk a lot in this city, too! Besides walking, we also used the subway system to navigate around the city. It’s definitely true, you’ll never be able to do everything on your list in one visit, so don’t over plan activities and pack in too much each day. We picked one major activity per day that was a must do/must see and it worked out well for us!

The boys’ first subway ride!

Of course, there are different activities based on the season you’re traveling. Some of our favorite New York City memories are riding the subway for the first time, going inside the Statue of Liberty, watching the Macy’s parade balloons being inflated, watching Elton John perform in the street in front of Saks, and finally seeing Naked Cowboy in Times Square!

Awesome experience getting to watch the Macy’s parade balloons being inflated the day before the parade!

Click here for my NYC summer guide with kids.

Click here for my NYC Thanksgiving guide.


We are in Philly!

We were so pleasantly surprised with our first ever visit to Philly! This city is fun, historical, and full of many different activities to explore. And it’s so easy to maneuver, which made it even better for me since I was there with my boys, without Jereme.

The Liberty Bell!

We visited Philadelphia in late June and were only there for three days. The weather was fantastic! It was in the low 80s while back home in Texas it was already pushing 100 degrees.

Independence Hall

I loved that we were comfortable to walk around the city from morning until evening! I feel like we left the city with more early American knowledge than ever before. The old buildings and historical sites, basically everywhere in Philadelphia, have me yearning for another visit!

The Double Decker Bus Tour

Philadelphia Must Dos:

We happened to visit the Betsy Ross House on Flag Day!

Be prepared to walk a lot in this city, too. Again, it’s very easy to maneuver, but we clocked in eight to ten miles each day exploring. The boys were a little older, one was almost seven and the other was ten during our visit.  

We walked to New Jersey on the Ben Franklin Bridge!

My favorite moments in Philadelphia were seeing the room that our Founding Fathers developed the ideas for our country in person, watching early American time period re-enactments, seeing an actual ghost on our Philly ghost tour, and watching my boys get excited to learn so much about Benjamin Franklin! We had an absolute blast and I hope we are able to return again soon with Jereme!

We have a strong love of learning in our family!

Click here for my complete guide to visiting Philadelphia with kids.



We road tripped to Chicago a few years ago on a total whim when we realized it wouldn’t take us that much longer to drive to than our yearly trips to Colorado. Since that first trip, I’ve traveled back another four times!

The Bean

Most of my trips to the Windy City have been in the summertime, only once did I visit in the fall. We love being outside, so walking around Chicago was something that my family enjoyed. In the spring and early summer, the weather is gorgeous, and I still can’t get over the flowers that are blooming virtually everywhere!

I loved the flowers!

My favorite trip was our first summer visit. We packed in so much and had a wonderful time together. Plus, I had previous students that had recently moved to the city from Texas, so they showed us all around!

The Chicago Riverwalk

Chicago Must Dos:

Dream come true! We’re at the Home Alone House!

Even though we had our car with us since we road tripped, we walked just about everywhere. We left our car at the hotel the whole entire time. We clocked an average of ten miles each day that we were here. We did brave the bus one time, but otherwise we enjoyed walking.

Walk back from the Planetarium

My favorite memories in Chicago are seeing Payton Manning filming on the Chicago River, eating delicious food the entire time, exploring the aquarium with my boys, and of course, seeing the house that Home Alone was filmed at!

Famous people, no big deal!

Click here for my complete guide to visiting Chicago with kids.



If you live near the Dallas area, or you want to visit Texas, this recommendation is for you! I’ve lived near Dallas my whole entire life, but never really visited as a tourist until last summer. My best friend and I took our boys for a few nights, and we truly had a blast!

A rooftop pool is a must!

We visited in July, and true to Texas, it was HOT. But, that’s not anything we’re not used to. We planned mostly indoor activities and booked a nice hotel with a rooftop pool.

We spent a lot of time swimming!

I wouldn’t really call Dallas a walkable city, we needed our car for most of the places we decided to visit. But, it’s not nearly as crowded as the other cities mentioned above and we never had any issues finding places to park. If you’re visiting from out of town, I do suggest renting a car!

George W. Bush Presidential Library

Dallas Must Dos:

The Reunion Tower

Even though Dallas is close to home, we still had such a great time on our “staycation!” We didn’t even get to do everything on our list, but fun was had by all. My favorite Dallas memories are visiting the George W. Bush Presidential Library, going inside the Reunion Tower and up to the GeO-Deck, lounging by the rooftop pool, and not having to drive too far on our road trip here from home!

The Perot Museum

Click here for my complete guide for visiting Dallas with kids.

No matter which city you plan to visit, a fun time is guaranteed! My boys both agreed that New York City is their favorite city of the five. Mine is Philadelphia! Be sure to check back soon to see what we’re up to next. And don’t hesitate to reach out if you have any questions!

How to do Chicago in 2 Days with Kids!

Hey y’all! This is Jasha here. I am so excited to share our quick trip to Chicago. I am not going to lie, I was NERVOUS to head to the windy city with the kids… without Jereme. But it ended up being SOOOO much fun! So let me start from the beginning…

I am famous for planning our next road trip while on a road trip haha! So, as I was driving us through Missouri, we decided that we had to go visit our dear friends that were staying in Chicago for the summer. We really didn’t have any idea how long of a trip Chicago would be from Dallas, but it turns out that it’s only 13 hours away! I mean, we drive that far to Colorado for our ski trips and we’ve definitely gone farther before. Once we ran the idea by our hubbies, we booked our hotel on Expedia (book now/pay later of course). Which was brilliant, because we originally planned to go in early July but we ended up stranded up in Wyoming and Colorado with our Yukon issues. I am so happy that we were able to go, we had a great time on this road trip!

We left on a Sunday afternoon and stopped in Joplin, Missouri for the night. Then we woke up early and ventured to Springfield, IL. Click here to see our All Things Abe Lincoln Blog! We finally arrived to our hotel late Monday night. We stayed at the Congress Plaza Hotel in Chicago. It was lovely. I was nervous about driving through Chicago & unloading our things in the city, you know these are the things Moms worry about when traveling alone. Fortunately, there was a little driveway to pull into and we valeted the car for the 2 days we were there. It did cost $50 per day, but I was okay with that price, mainly because we didn’t really have a choice! We pretty much went straight to bed so that we could wake up early and get together with Roz and the girls! Their apartment in Chicago is amazing! Check out these views of the lake!!

The Wright’s Lake House

Day 1: Our hotel was only 2 blocks away from Roz’s “lake house.” We walked straight to their place and then headed to breakfast. After we ate, we started our adventures with the kiddos. We had the best tour guides, too! Emma and Hayley (my former kinder and 1st grade students) were the best at guiding us through the city! We walked from breakfast to Shedd Aquarium, which is another place I’ve added to my list of “places to work when I grow up” haha! There was so much to see and do. I don’t think we even touched the surface of all the things there, but we did see some neat exhibits and watched a dolphin show! The kids also found some great souvenirs! You can actually see the aquarium from the Wright’s apartment, so I am sure you can imagine how gorgeous the walk was back to their place. We took in the sights from the city and went back to swim in their pool and hot tub! After swimming, we went back to the hotel for a quick rest/do some work (I was still styling for Stitch Fix at the time). We met back up with Roz and the girls and had some deep dish pizza at Gino’s East. Then we called it a night. We walked a grand total of 8.1 miles this day and the kids did awesome!

Walk along the lake to Shedd Aquarium

Shedd Aquarium

The fountain from Married with Children LOL!

The most beautiful pool I’ve been to!

These kids have it so bad ha!

Had to pose with some deep dish pizza! My secret… I hate pizza LOL!

Day 2: I think this day was my favorite! We met up with Roz and the girls at The Bean. It was so sunny and bright, but we were able to snap a few pics to mark our time here. From The Bean, we actually loaded up on a bus and took public transportation to the famous Portillo’s for lunch. My anxiety was through the roof in this place. So many people, so many choices, so many workers yelling. But let me tell you, THE FOOD IS WORTH IT! I had the best chopped salad I have ever had with a side of Italian beef LOL. It was to die for! After lunch, we walked through downtown Chicago down by the river. This city is so beautiful. Then, we went to Jojo’s Milk Bar for a fun treat! Check out these milkshakes!!! They were an instant tummy ache, but oh so yummy! From here, we took the kids to Adler Planetarium. It was super cool and kept the kids entertained for hours! It was another fabulous walk back to the hotel and we had fun spending some time out by the lake on our way back . We finished the day with dinner at Roz’s and watched a firework show over the lake from their living room! Apparently, there’s a firework show over the lake every Sunday and Wednesday in the summer. Then, we hugged the girls goodbye and went to the hotel for our last night in Chi-town. As you can tell, we packed in a lot for our two full days in the city. And, we walked a grand total of 10.3 miles this day!

The Bean

Braving the bus!

Inside Portillo’s

jojo’s Milk Bar

Adler Planetarium

Fireworks over the lake!

Day 3: We had to head back this day, but we were SOOOO close to the infamous Home Alone House. I mean, when you’re only 20 miles from the filming location of the BEST Christmas movie of all time, you have to go visit. OMG, I was so nervous the closer we got. I didn’t know what we would encounter. But I was also super excited. I honestly think I may like this movie more than my kids. When the house came into view, I was pumped! This has been a dream of mine for years! We parked the car, jumped out and took the quickest pic in history haha! Looking back, I wish I would’ve knocked on the door and asked for a tour. Click here for the address.

My childhood dream come true!