5 Things to Do and See in Chicago


Dress: Madewell | Sunglasses: ZeroUV

Dress: Madewell | Sunglasses: ZeroUV

Chicago River

The "Windy City", also known as Chicago, certainly lived up to it's comparison to New York. The "cleaner' version of New York that is. After a week in Chi Town, I fell in love with the architecture, the food, and the people. I cannot wait to return and explore some more, but in the meantime, here are a few things I recommend for your next trip to Chicago!  

1. Chicago Architecture Boat Tour

Outfit from Madewell | Sunglasses from ZeroUV

Outfit from Madewell | Sunglasses from ZeroUV

If you have 75 minutes to spare, I highly suggest taking a boat tour through the Chicago River and learn about the amazing architecture in the city.

The architecture boat tour has several scheduled rides throughout the day to fit your schedule is around $30 per person. It's great if it's your first time in Chicago or if you want to simply chill out and see some great stuff. The boat tour includes a bar, so go ahead and get in an afternoon drink or two while you're on board. 

2. Millennium Park

Wearing Kenneth Cole vest, Madewell bag, and Sam Edelman boots.

If you're looking for the famous Cloud Gate, also known as "The Bean", you'll find it in Millennium Park, along with a few other popular areas such as the Jay Pritzker Pavilion and Crown Fountain.

Make time to explore the area for exhibits and events that may be occurring. The park is always open and typically busy, but of course, quieter on the weekdays. Click here for the monthly schedule of events.

3. Cindy's Rooftop

After visiting Millennium Park, walk across the street for drinks with a view at Cindy's Rooftop. This gorgeous gem is located in The Chicago Athletic Association Hotel and is usually pretty crowded, as it is known for it's amazing view of Millennium Park - from above. Expect to wait in a line to take the elevator up to the rooftop, but make sure to take your time and enjoy a cocktail and some light bites. 

I absolutely loved the aesthetics of this place and it is one of my favorite places that I visited while in Chicago. Thanks to our friend and "tour guide", Cress, for showing us this spot! 

4. Navy Pier

Celebrating it's 100th year, the Navy Pier is Chicago landmark that is worth checking out. We had a great time exploring the indoor shopping area and were reminded of our childhood with the rides outside. 

I loved the view here, although I'm a suckers for views anyways. Take the kids, bring the family, and your loved ones to watch the sunset here. 

Tip: Adler Planetarium - Skyline View

For a great view of the city, visit Adler Planetarium for a nice, quiet, and relaxing wind down session. It's the perfect place to just think and be in peace.

Alternative: SkyDeck

Located at the Willis Tower, the SkyDeck is one of the most popular attractions of Chicago. Be prepared to wait 30-45 minutes, unless you can arrive before they open at 9AM. Price ranges from $22 to $49 for the FastPass.

5. Chicago Cultural Center and Art Institute 

Got some time to kill and want to be inspired? Check out the Chicago Cultural Center, which has amazing architectural designs within the building itself. Monthly schedule includes music, exhibits, and you can even have your wedding here. 

For a couple hours of fun, I suggest the Art Institute of Chicago. It's $25 for out of state visitors and $20 for Chicago residents, but if you have a school ID - use it for a discount! They also have package deals which include tickets to SkyDeck and Navy Pier rides. 

With the wide variety of art exhibits on display, you will spend a minimum of 2 hours touring through the entire museum. My favorite exhibits included photography and the miniature room. 

Events in Chicago

While the above mentioned are always available to see and do in Chicago, here are two special events I was invited to while I was out there. 

Dose Market

Dose Market is an experience combining shopping, food, and fun! It happens ever so often and I was lucky enough to be in town for it.

Dose brings together chefs, fashion designers, and artists to give you one location to get all your goods from. It was an organized visual upon entering, easy to maneuver, and I had a great time exploring all afternoon. Thanks so much for having me!

P.S. The next one is in December and you can find more info here

Millie Brown Virgin Hotels Chicago Takeover

Ever dined in the dark? I can now say that I have!

I was fortunate to be in town for the #VHCxMillieBrown event at Virgin Hotels. Combing live art and music, Millie Brown brought her talents to Chicago and teamed up with Pablo Dylan for an unique performance and special night.

From the performance to dinner, everything I saw blew me away. It was something I never had seen before and probably won't have the chance to witness again. The dinner itself was gorgeous and delicious, plus the vibes all night were on point.

Thank you so much for having us during our stay in Chicago!

Stay tuned for my round-up for Chicago places to eat!