cloud gate chicago

3 Day Chicago Itinerary

I spent 5 days in Chicago, Illinois last week, & I’m already looking forward to going back! Since it’s a 4+ hour flight from San Francisco, California to Chicago, Illinois, I did my best to pack as much as possible into 3 days, & I definitely succeeded! I managed to do everything that I wanted to do & more. That said, here’s my 3 Day Chicago itinerary!

Day 1: Millenium Park, Brunch at Cindy’s Rooftop, & Lincoln Park

Despite the 2-hour time difference, I was up bright & early for my first day of exploring. I stayed at Claridge House, which was only a 2-minute walk from the Clark & Division Red Line stop. Before arriving in Chicago, I met a very kind lady at the San Francisco airport, who recommended using the “L” train, and reassured me that it was very efficient and so much cheaper than San Francisco’s BART (Bay Area Rapid Transit) train. I ended up buying a 7-Day CTA pass for unlimited rides, & I’m so glad I did!

Cloud Gate “The Bean”

Like any Chicago tourist, our first stop was Millenium Park to see Cloud Gate “The Bean”. We got there early in the morning to ensure there were fewer people around to get the best pictures. We then spent the next hour wandering around the park to see the Millenium Monument, Lurie Garden, Crown Fountain, & Jay Pritzker Pavillion.

After exploring Millenium Park, we went to Cindy’s Rooftop for brunch! Cindy’s has not only a delicious menu but also amazing rooftop views overlooking the park. As I’ve mentioned, brunch is my favorite meal of the day. I also love having brunch as a way to save money while I’m traveling, so that I only have to pay for 2 meals for the day rather than 3.

After brunch, we headed back to the hotel for a quick rest. Then, we walked over to Lincoln Park. Claridge House is only a 14-minute walk from Lincoln Park, & it’s such a cute neighborhood. Most of the houses I walked past were fully decorated for Halloween. At Lincoln Park, I saw animals at the FREE Lincoln Park Zoo, flowers at the Lincoln Park Conservatory, the Lincoln Monument, the Alfred Caldwell Lily Pool, & so much more.

That evening, we had dinner with my sister’s co-worker at GEMINI. I had water & the San Pancho cocktail to drink. Then, my sister & I shared a Baby Wedge Salad, Steak Frites, & a Pineapple Upside Down Cake for dessert. We were so hungry after exploring all day that this was the only meal I didn’t manage to photograph. lol

Day 2: Shopping, Brunch at Little Goat Diner, Skydeck Chicago, Three Dots & a Dash, & Blackhawks Hockey Game

On day 2, I took the train to do some shopping. I’m a huge Kristin Cavallari fan, so I had to stop by her Chicago Uncommon James location. I bought a Cross Ring & Strawberry Fields Earrings.

After shopping, we had brunch at Little Goat Diner. I had coffee & a Kimchi Spiced Boody Mary. Then, my sister & I shared the Smoked Corned Beef Hash with Eggs, a single Apple Cinnamon Pancake, & a fruit cup. The food was delicious, & our waitress was an awesome Chicago native who gave us the inside scoop on what else to do/see/eat during our trip.

After brunch, we hopped back onto the L to Skydeck Chicago. The interactive experience brought you through several rooms with information about famous Chicago landmarks & history. Then, we headed up to the 103rd floor to take pictures in the beautiful glass Skydeck above the city. Afterward, we hopped back onto the L back to our hotel to rest a bit.


Next, we went to the cutest speakeasy tiki bar, Three Dots & a Dash. First off, let me say that my two favorite types of bars are tiki & speakeasy. (The only other bar I’ve been to that was also both was False Idol in San Diego, which I highly recommend too.) I had delicious crab rangoons & two cocktails, Painkiller & Aloha Felicia #4.

Isle of Mango & Aloha Felicia #4

After the quick Happy Hour, I headed to the United Center for a Blackhawks hockey game! I’m not a big hockey fan, but I’m a HUGE live sports fan. I honestly wanted to catch a Cubs game at Wrigley Field & possibly get a tour of the stadium. Regardless, it was still so much fun to cheer on the Blackhawks. Plus, tickets were also only $27! After the game, we took the L back to our hotel & called it a night.

Day 3: Chicago Architecture River Tour, Chicago Riverwalk, the Magnificent Mile, Portillo’s, Jojo’s Shake Bar, & Bulls Basketball Game

On day 3, we did a Chicago Architecture River Tour, & this was actually my favorite activity. When I travel I love learning about the local architecture in addition to the history, so this tour was the perfect combination of both. (My Dad is a Civil Engineer, so I’ve always had an innate love of architecture, which is also why I love Europe. So much architecture & history!)

After the tour, I walked along the Chicago Riverwalk & the Magnificent Mile. We then headed to Portillo’s for lunch. I had a classic Chicago Style Hot Dog. (No ketchup!) Then, my sister & I shared fries & onion rings.

After lunch, I went back to the hotel to rest. Then, for Happy Hour, I went to Jojo’s Shake Bar! I had a Witch’s Brew cocktail, a loaded grilled cheese, & shared a Pumpkin Patch Shake for dessert!

Pumpkin Patch Shake

After Happy Hour, I went to opening night for the Chicago Bulls at the United Center! I even got a free T-Shirt! I’m a huge basketball fan by the way. My team is and will always be the Golden State Warriors, but who doesn’t love the Bulls right?! I love Michael Jordan, Scottie Pippen, Dennis Rodman, & I was obsessed with watching The Last Dance docuseries.

After the game, we hopped back onto the L to our hotel to start packing up for our last half day in Chicago. It was a lot packed into 3 days, & even though I still wasn’t able to check out Navy Pier or see the Cubs, I look forward to coming back to Chicago again! I hope my itinerary helps you plan out your own. Safe travels!

XO Denise

view of white airplane wing over the clouds

How-To: Plan a Vacation

I’ve been told that my planning skills are extraordinary! In a team meeting a couple of months ago, I shared my personal color-coded Google calendar, my sticker-filled, colorful, Happy Planner, & my personal Evernote notebooks for work, travel. Today, I’m going to share with you how-to: plan a vacation process, using my favorite planning tool, Evernote.

Choose a Destination & Research

Choosing my destination is usually the first step. I personally have a list of destinations on my phone that I use as a quick reference. I take into account the time of the year that I want to travel, the time it would take to reach my destination, as well as how much time I have to take off. For international travel, I like to have at least 10 days. When camping, glamping, taking road trips, or traveling to the Midwest or East Coast, I like to have a long, 3 or 4-Day weekend. And a short weekend is usually enough for vacations on the West Coast, since I live in California.

Once I choose my destination, I do my research, & I mean I do thorough research! I also look up everything I need to know, creating lists of must-dos, must-sees, & must-eats. I decide on the best days to travel & for how long to optimize everything I want to do. Lastly, I start budgeting & brainstorming how to save money during the planning process as well as set aside spending money during my adventures.

Add My Findings to a Travel Itinerary

Depending on how many days I have to travel, I create a flexible itinerary to outline my plans for my trip. I list my travel dates, flight info, & even the weather forecast to determine how to pack. I decide what I want to do & eat each day, but leave room for flexibility just in case the weather changes or we come across planning issues. Here’s an example template from my vacation in San Diego, California last Fall.

Finalize a Packing List

My last step is creating my packing list. In the example template above, I have a full Packing Checklist. Listing everything I can possibly need as well as choose specific outfits for certain days allows me to avoid forgetting anything & over-packing. I also created a travel essentials blog post a few weeks ago that has some of my favorite things to always ensure I travel with.

I hope sharing my how-to: plan a vacation process helps you plan your next vacation! Do you have any other tips & tricks that you’d like to share with me? Please do share them in a comment below.

XO Denise

My Top 10 Travel Essentials

Travel has been a significant part of my life since I was young. I took my first flight on an airplane at 9 years old. My family & I flew down to Los Angeles then took a Carnival cruise to Ensenada, Mexico. In the years that followed, my parents also blessed my siblings & me with the opportunity to explore Hawaii, Germany, France, & the Philippines. As an adult, I’m grateful to have been able to revisit some of the places that I visited as a child as well as the Bahamas, China, England, Italy, Japan, Spain, & Thailand. If you’re a fellow travel addict, you’ll relate to my love of exploring a new place & immersing yourself in its culture & history. After years of travel mishaps without the basic necessities, I want to share my top 10 travel essentials!

My Top 10 Travel Essentials

#1: Passport Holder

You don’t ever want to forget or lose important documents while traveling, especially your passport. My passport holder is not only adorable but also very easy to spot when searching through my carry-on. I love to keep a close eye on where my passport is at all times.

#2: Sun Hat

Despite being born brown, my skin is very sensitive to sunlight. Ever since I was a little girl, I learned to always wear sunscreen with at least 30 SPF & wear a hat to limit exposure under the sun. This sun hat matches all of my outfits & works for so many different activities & occasions. I get compliments on it everywhere I go. My hat was first purchased for a 10 day trip to Thailand, but since then it’s also been to Lake Tahoe, Las Vegas, Napa, & San Diego.

#3: Travel Neck Pillow

Neck pillows get a lot of hate, but I love mine! Especially if you’re going to be on a flight for more than 3 hours, a neck pillow will be your best friend. Sleeping on an airplane is hard enough, so anything that can help your ability to nap more comfortably is needed in my book. My current travel neck pillow is also super cute & resembles a mermaid tail.

#4: Portable Charger

While I’m traveling, I use my phone to navigate as well as translate when I’m in a non-English speaking country. There’s nothing worse than having your phone’s battery die when you’re lost in an unfamiliar place & unable to communicate with people around you. Having a fully charged portable charger on hand will be your savior at the end of the day.

#5: Adidas Slides

First off, I LIVE in my Adidas slides! Sadly, my pug destroyed the original pair that I bought in New York City. 🙁 When traveling, they’re even more of a life-saver. They easily slip on & off when you’re going through airport security, & I love having my own slides to wear to the beach or around a hotel or resort.

#6: iPad Air

I always pack my gold iPad Air 2 in my carry-on. Sadly, not as many airlines offer built-in screens for long flights as before. So, to keep myself entertained, I use my iPad Air to read, practice drawing using my Apple pencil, listen to music, & watch movies.

#7: Apple AirPods

Most airlines require you to wear headphones. You’re not allowed to have your device’s volume blasting & disturbing other passengers during a flight. I love that my AirPods have no wires to get tangled up in my carry-on. It’s easy to quickly connect them with Bluetooth to my iPad then slip them into my ears. I also keep mine in this adorable dumpling case!

#8: Wipes

Give me ALL THE WIPES! I love wipes for my everyday life, but when traveling, wipes simply make my life easier. I use lens & screen wipes to clean my electronic devices & my glasses. Clorox wipes are great for surfaces on the airplane around my seat as well as in the bathroom. I use baby wipes for the foreign countries that don’t provide toilet paper in public bathrooms, & I use makeup wipes to remove any remaining makeup off of my face at the end of the day.

#9: Hanging Toiletry Bag

I travel with a toiletry bag with a hanging hook. This allows me to have easy access to all of my toiletries in one spot without taking up too much counter space. Sometimes, when you travel with a big group of people, you’ll want to ensure there’s enough space for everyone without hindering your own hygiene routine.

#10: Laundry Bag

There’s nothing I hate more than forgetting to pack a laundry bag! Growing up, I would settle for any plastic bag that my mom had lying around, but as I’ve gotten older, it’s become more important to me to ensure that I keep my dirty laundry completely separated from my clean clothes. This laundry bag is compact & easy to pack at the beginning of your trip but expands as needed as your trip progresses.

What are your Top 10 Travel Essentials? Do you share any of the same ones that I have? Let me know in a comment.

XO Denise