Chicago has been sitting on my travel list for a long time.
I remember passing through the Windy City when I was younger while my dad was heading north to pick up a vehicle. I was probably around 13 at the time, and while we technically saw Chicago, we didn’t really experience it. Ever since then, I’ve wanted to go and actually explore the city properly.
Fast forward to 2018 in college, a few friends and I made one of those casual promises people usually don’t hold:
Once we graduate and get real jobs, we’re taking a trip to Chicago!
Jump to 2026, and we held true to it!
One of the things that made Chicago such an easy choice for us is that it has a little bit of everything to enjoy. Baseball, museums, food, architecture, parks — there’s enough variety that everyone in the group could find something they were excited about.
Early on, we agreed on one thing:
If one of Chicago’s MLB teams happened to be in town during our trip, we were going to a game.
That ended up helping us choose our travel dates and became one of the foundations for the entire trip.
Giving Ourselves Plenty of Time to Plan
Even though the idea for this trip started years ago, we officially began planning around September of 2025. Since we’d travel in May of 2026, that gave us around eight months to slowly piece everything together.
And I’m glad we gave ourselves that much time.
Trying to rush a trip together — especially with multiple people involved — can create quite the headache! Planning ahead gives us room to coordinate. We could monitor flights, compare hotels, work around schedules, and slowly build an itinerary without feeling pressure.
It also gave us time to actually plan carefully throughout the process.
One of the biggest mistakes people make with travel is waiting too long to book things. Flights climb, good hotel options disappear, and suddenly you’re either overpaying or settling for what’s left!
For trips in the U.S., I personally think having 3 months to prepare makes the experience much smoother because having a solid foundation makes the trip itself better, which reduces stress.
Building the Foundation for the Trip
Once we officially committed to our Chicago trip, the big questions started popping up:
- Where are we staying?
- Which airport are we flying into?
- How walkable is everything?
- What absolutely has to make the itinerary?
- How much are we willing to spend?
Answering these questions created the foundation for our trip.
Our group had a few major interests that shaped our planning. Some members of our group are huge fans of baseball, so attending an MLB game would be one of our priorities. We are also a group of foodies, thus trying the deep dish pizza, signature Chicago Dogs, and other bountiful foods was a requirement!
Some museums will be a major interest for us as a group. The Field Museum was an immediate priority to the itinerary. The museum happened to be hosting the Pokémon Fossil Exhibit during our trip dates, which made this attraction even more attractive to our group. Since most of us grew up loving Pokémon, this museum paired with the exhibit became all of our #1 Must See Attraction on this trip!
When it came to lodging, everyone had slightly different priorities. Personally, I wanted:
- Easy access to transportation
- A centrally located hotel
- Walkability to major attractions
- A decent city view
- Strong overall value for the price
I’ve never been someone who simply chooses the cheapest option. I look for the best value — the most “bang for my buck.” In the end, I focused on finding a hotel near The Loop that would give me quick access to Chicago’s major attractions while still fitting into the budget.
After some research and comparison, my choice of lodging would be the Whitehall Hotel on Delaware Ave for this trip. I almost selected a Hostel due to a better price but my partner was not in agreement. 3 major attractions for me would be attending a White Sox Baseball Game, Field Museum, and Skydeck. These would lay the foundation for my trip and where I would begin with my itinerary creation.
The next piece of laying down a foundation would be how would we get around in the city? What better way to get around other than the transit system available via train and bus plus some walking! (I absolutely love public transportation systems)
Now we can build upon our foundation and shape our itinerary with the building blocks of transportation, starting point, and our must-do attractions on our list!
Shaping the Itinerary
Once we had the foundation of the trip laid out, I began loosely shaping what our days in Chicago could look like.
I’ve never really been someone who enjoys a rigid itinerary while traveling. Personally, I prefer being in a general direction for the day rather than feeling like every hour has been decided before I even arrive, but with multiple people involved I made an itinerary with rough timelines to help us have dedicated times to spend together as a group.
Instead of building a strict schedule, I focus on creating a flexible outline built around the bigger things we knew we wanted to experience as a group, plugged times in to showcase major attractions, times for lunch/dinner which we would try to stay true to, and if anyone wanted to find me they’d know where I’d be.
For our group, the Field Museum and baseball game would be major centerpieces of the trip. After comparing schedules, we decided Saturday the 23rd would probably work best for the Field Museum, while the Chicago White Sox game on the 25th became our baseball day together.
Those became our anchor points along with a few lunch or dinner times guaranteed to spend time with the group.
Everything else around these attractions stayed intentionally flexible. This is how I travel, and prefer it this way. It allows me to do as much as I’d like to on a trip while leaving time for variables out of my control!
I like having anchors along the trip – major items we know we are doing 100% – while leaving room for exploration, room to wander, and change plans on the fly as needed!
While researching Chicago, it became prevalent that timing matters for certain attractions. Places like Skydeck and Chicago 360 can become extremely crowded later in the day, so mornings seemed like the better move.
The Field Museum also seems like the kind of place where you could accidentally lose an entire day without realizing it, so I wanted to leave plenty of room for that too. Especially if this museum is anything like the American Museum of Natural History in New York City.
One thing I enjoy doing when forming an itinerary is grouping nearby attractions together cohesively.
For example:
- Millennium Park
- The Bean
- Grant Park
- The Field Museum
These flow together well geographically, so it makes sense to connect them into the same day instead of constantly bouncing across the city.
That’s how I approach travel planning:
Identify the major “must-see” locations first, then slowly connect the attractions around them.
You could go to Millenium Park, catch a game at Wrigley Field, then go down to Hyde Park but you’d spend a lot of time travelling between the places!
Below is the structured-flexible itinerary I put together for our Chicago trip.
You may notice when looking through our plans that most activities have rough times attached to them. Those times aren’t meant to create a rigid schedule or force us to rush from place to place.
Instead, they’re there to help us establish a rhythm for the day.
For example, if the Field Museum opens at 9:00 AM and is one of our priority attractions, it makes sense to start our morning around opening time. Likewise, if we know a baseball game starts at a certain hour, we’ll build the rest of the day around it.
Meal time is another item roughly timed in our plans. Everyone travels a little differently, and some members of our group definitely prefer knowing when and where the next meal is happening. Rather than wandering until someone gets hungry, we’ll identify lunch and dinner windows so everyone can enjoy the day without worrying about missing a meal.
These meal times help us experience some of Chicago’s food scene. Whether it’s grabbing deep dish pizza, finding a local restaurant for dinner, or stopping somewhere along the way that caught our interest, having rough meal windows allows us opportunities to enjoy the city’s delicious food.
At the end of the day, these times aren’t strict appointments. They’re simply guideposts that help us balance attractions, meals, transportation, and downtime while still leaving room for spontaneous discoveries along the way.
Pinning Our Priorities
When travelling, not all tasks and attractions should be treated equally. In a group, every one is going to have an activity that is prioritized more than others.
During travel, there are 3 categories I put attractions as:
Must Experience – Items or attractions at the top of our list. We’d be disappointed if we missed this.
High-Interest Stops – These are items we individually place a high value on. We may be upset if we can’t experience this item, but we won’t feel like we missed out on the trip. These stops will typically fill in around your must experience items.
Flexible Opportunities – These are items that may be plan C if B can’t be met. if weather changes course you’ll do this, or if something pops up and it grabs your attention. These will be the most negotiable pieces on everyone’s itinerary, but be careful on the negotiations. Your flexible opportunity may be someone’s Must Experience, and they will be upset when you chalk their prized attraction down to unimportant.
Every person is going to put items in different spots on this list. Everyone may put the same attraction as Must Experience, there will be some that a Must Experience for one is a High-Interest or Flexible Opportunity for others.
I like to ask everyone what is an item or two that they must do before returning home. This will develop the itinerary as you’ll find many Must Experience and High Interest items from everyone and these will be prioritized.
Fine Tuning Before the Trip
With the foundation built and our plans mostly in place, the last thing left to do is a little fine-tuning before we leave.
About two weeks before departure, I’ll start checking over everything one last time. Not because I expect major changes, but because little details have a way of sneaking up on us if we don’t pay attention.
The first thing I’ll begin watching is the weather forecast. While some attractions on our list are locked in place, others can be moved around if needed. If one day looks like it’ll be sunny while another has rain in the forecast, I’d rather spend the nicer day walking around the city and save indoor attractions for the rainy weather.
I’ll also start checking operating hours for attractions and restaurants we’ve talked about visiting. Sometimes places change hours, close for private events, or aren’t open on the day you expected them to be. I’d rather catch that while sitting at home than while standing in front of a locked door in Chicago. (This happened in The Netherlands and New York, I know it will happen in Chicago too)
This is also when I’ll confirm my flights, hotel reservations, attraction tickets, and look into things like luggage storage or early/late check-in options. Arrival day goes smoother when we already know what to expect.
As departure gets closer, I’ll begin laying out what I’m bringing and making adjustments to my packing list based on the forecast. Comfortable walking shoes are always guaranteed, but things like jackets, or extra layers depend entirely on what Chicago decides it wants to do that week. If rain is expected, I’ll have a light rain jacket in my bag. I’ve never been a fan of umbrellas, and much prefer keeping my hands free while I explore so I can take photos, carry food or use them for anything else than holding the umbrella.
By this point, the major planning is finished. The foundation has been built, the attractions are chosen, and the itinerary is ready. The final days are really just about making small adjustments and getting ready for the trip ahead.
Then it’s time to pack the bags, check into our flights, and finally see what Chicago has in store for us.
Finally, Heading to the Airport
After years of talking about this trip, months of planning, and countless conversations about what we wanted to see, Chicago is finally within reach… literally as I’m making my way to the airport.
The foundation has been built. Flights are booked, hotels are reserved, attractions have been selected, and our plans are ready, we just have to show up! There will undoubtedly be changes along the way, and that’s perfectly fine. Some attractions may take longer than expected, weather may shift our plans, and we may stumble across something completely unexpected that wasn’t on our radar at all.
That’s part of the fun of travel.
At the end of the day, this trip was never about creating the perfect itinerary. It is about finally making good on a promise made years ago, spending time with friends, exploring a city we’ve wanted to experience, and creating memories along the way.
Now all that’s left is going through TSA, and making it to the gates for our flights, and touching down in Chicago!
Chicago, we’ll see you soon.
As always, thank you for reading, and remember…
It’s Turtle Time!
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