I lived in Chicago for one year while my dad was completing his last year of grad school when I was
about 7 years old. My family almost stayed put there but ended up moving back to California. In my
freshman year of high school, we visited again because I had a basketball tournament there and
remembered how much we loved it. We have visited every summer since then. What makes Chicago a
cool place to visit is the clean, fresh vibe while having a modern, big-city feel. Chicago has four
seasons, and depending on the time of year you choose to visit, your trip will have a slightly different
itinerary.
Where to stay
My family has stayed in the Lincoln Hotel the last few years located in Lincoln Square Park. It’s North
of the Loop. We prefer this area because it is safe, clean, and close to a lot of the things we like to do,
which makes pretty much the entire trip walkable for us. The service at the Lincoln Hotel is great.
There is also a rooftop restaurant and bar with a spectacular view of the city and its skyscrapers. If
there’s a different area you would prefer to stay in, we can accommodate a hotel in that area for you
as well.
Transportation
Chicago is a very walkable city. It’s also super easy to navigate yourself since the city streets
are essentially laid out like a grid. I can get around by myself and I’m incredibly directionally challenged.
If you need to get somewhere farther than you can walk, transportation is easily accessible as well. You
can call a taxi or an Uber. If I can’t walk somewhere, I will likely be taking the L-train, similar to a
subway.
Weather
My favorite time to visit Chicago is certainly the summer. It’s warm and gorgeous and there’s lots to
do. Winter is quite literally the opposite of summer, but will still be a cool experience. Winter can be
very cold, so if you choose to visit during this time, bring your warmest clothes. There’s still plenty to
do and you can probably even find a place to go sledding. Spring and fall are similar temperature-wise.
I remember fall being very pretty when I lived there, same with spring. You can’t go wrong when you
choose a time to go to Chicago, you just have to be properly prepared.
What to do
The options are endless when it comes to things to do in Chicago. One of my favorite activities I did in
Chicago was this last summer. My parents took my brother and me to see a Second City show for the
first time. If you’re unfamiliar with what Second City is, it is a comedic performance put on by a few
actors/actresses. These entertainers often go on to act at SNL. Second City is now a must-do for me
every time I visit Chicago. The show was hilarious and very entertaining. I didn’t order any food there,
but they serve food and drinks and the menu looked decent. Another favorite of my brother and mine
is jumping into Lake Michigan. We can walk to a ledge to jump off about half a mile from where we stay,
it’s just outside of Lincoln Park. Last time we were visiting we jumped in the lake about 50 times per
day, not exaggerating. If you’re not into jumping in, you could also have a relaxing beach day. Lake
Michigan is like a freshwater ocean, you can’t see the opposite end of the lake. I also enjoy shopping
and Chicago is one of the best places to visit for this. I often go to the Water Tower Palace and the
Magnificent Mile. My youngest siblings loved the Lincoln Park Zoo and it’s free to visit. The nightlife
here is very vibrant since there are plenty of clubs and bars. There’s also a number of sports teams
you can go watch (I suggest a Cubs game at Wrigley Field), art museums to visit, and local concerts,
considering Chicago’s musical legacy. A jazz club would be fun. Lastly, you can go to the top of Willis
Tower or see The Bean for some good sightseeing.
Where to Eat
This is something my family knows all too well. Chicago has such an amazing food scene it will blow
your mind. My family gets donuts every. single. morning. We go to a tiny store named Donut Vault
(they also have a donut truck going around sometimes). We went while we lived there all the time and
will not miss going when we visit. When the Donut Vault first opened, there would be a line out the
door and around the block and the donuts would be sold out before lunch. Donut Vault is still popular
but their donuts are thankfully no longer sold out that quickly. My family got on their website one time
because we chased down their truck to be the first customer of the day. Donut Vault has a flavor of
the day, which is always so creative. This week some flavors are birthday cake, carrot cake, apricot jelly
filled, coffee caramel old fashioned, peanut butter and jelly, strawberry lemonade, chocolate chip
pancake, and raspberry cheesecake. Their classics are still my favorite though. I love a good chocolate
old-fashioned. They have pretty good coffee to go with the donuts as well.
For lunch, we usually pop into any place that looks yummy while we’re out walking. This last visit we
went to a brunch place named Blue Door Kitchen and Garden. The ambiance was so adorable (very
Instagram-worthy) and the food was delicious. For dinner, we usually make a reservation online. A few
of our favorite dinner spots are Gibson Bar and Steakhouse and Hugo’s Frog Bar & Fish House.
Chicago is a beautiful city and very well-kept. I have loved it since I was a kid and it’s great for all ages.
It can be family-friendly depending on how you plan your trip. I believe there’s something here for
everyone. It’s filled with cultural diversity, stylish people, and historical architecture. There’s lots to do
and eat. If you are interested in booking a trip to explore the Windy City, let us know and we can help!