Welcome to the city of deep-dish pizza and beautiful architecture. Where towering skyscrapers meet beautiful beaches, and big city lights make for a romantic date night. Chicago, a city rich in history and culinary diversity, offers visitors a variety of dining, drink and destination options that are sure to satisfy any appetite.
So, what to do, what to see and what to eat when in Chicago? On our five day trip, these were the top things on our list:
EAT: The Hampton Social
Located in the River North area of Chicago, The Hampton Social perfectly executed the preppy, nautical vibe. From the moment you walk into the restaurant you can only assume that you have arrived in the East Coast’s very best spot. Boat wood ceilings, columns wrapped in rope, and a few hammocks located in the casual seating nooks are just a few of the elements that bring The Hampton Social to life.
We ordered the prosciutto pizza and rock shrimp and that was just enough for a quick bite for two to celebrate a special someone's birthday.
EAT: Stan's Donuts
Stan's Donuts was a must visit on my list. Stan's is an uber famous over 50 year old donut shop from LA that has made its way to Chicago and has won our Midwest hearts. Stan's has donuts, coffee and gelato. I recommend trying the peanut butter pockets or the pistachio donut - OMG...unreal!!!!
EAT: XOCO Chicago
We brunched at the infamous XOCO Restaurant Chicago which is an adorable quick-serve Mexican eatery on the North Side that features mouthwatering breakfast, lunch, dinner, and desserts created by mastermind Chef Rick Bayless!
XOCO Chicago has become a staple for Chicago with it's contemporary Mexican dishes, famous chef, and tasty desserts!
DO: Sunset Cruise
We decided last minute with the advice of friends to do the sunset boat cruise. it was about $35US and worth every dollar. It was a perfect night and we lucked out as sunset was a beautiful candy coloured sky. It's definitely a great way to see the city and learn some history at the same time is by doing a river cruise. Our cruise lasted about two hours and we were able to see a lot of the city during this tour as well as learn about major events that have shaped the city and the different styles and types of architecture that make Chicago what it is today.
DO: Visit the Skydeck at the Willis Tower
Because there's nothing like standing 1,353 feet in the air in a glass box that extends out 4.3 feet from the rest of the building. If you have the courage to step out on the ledge, the skydeck makes for great Instagram pictures, great stories to share with family/friends and most importantly, it's inside so you are warm and don't have to worry about the cold Chicago winds.
HOWEVER....we didn't get to experience this as the line up was absolutely crazy!!! My advice is to arrive before it opens. (9:00am during the summer and 10:00am during the winter months). This way you’ll be one of the first people in line to catch the elevator to the top.
I did manage to snap this photo in front f the building though...haha ;)
DO: Explore the Chicago Riverwalk
I know what you’re thinking, you’ve seen one riverwalk, you’ve seen them all. You couldn’t be more wrong. Chicago’s Riverwalk is one of my favorite things about the city. Some of the best views of Chicago can be found on the city’s riverwalk. Not only that, but in the summertime, it’s a great place to hop on a river cruise and see the city from a different vantage point. The Riverwalk is currently in the process of being expanded 9 blocks, which is scheduled for completion later this year.
DO: London House - for the incredible views!
Without question, the rooftop bar, LH on 22, is the most coveted spot at LondonHouse. The rooftop bar boasts some of the best, unobstructed, rooftop views of the city and has a great mix of inventive cocktails, drinks, and small plates. A picture is worth a thousand words, so a trip to the beautiful London House is an absolute must while visiting Chicago.
DO: Take In A Cubs Game at Wrigley Field
Even being a die hard, forever in love Toronto Blue Jays fan, nothing quite says, Chicago like the Cubs. At 102 years old, Wrigley Field is one of the oldest fields in Major League Baseball, second only to Boston’s Fenway Park (104 years old). If baseball history is something you’re interested in, book a tour of the field. If just taking in a game is more what you’re looking for, head to Wrigleyville well in advance of game time. We actually got standing tickets to the last home game of the season before play offs and trust me, even the standing tickets were amazing. The field alone is just beautiful and the views from all around was perfect. This was actually the highlight of our trip for me as I love baseball and have huge respect for the Chicago cubs! Plus I was able to cross off another item off my bucket list: to attend a game in every baseball field in the MLB.
SEE: The Sights at Navy Pier
Navy Pier is probably the most touristy thing to do in Chicago. Personally, I found it rather boring until we arrived at the very end of the pier, where we found pretty views of Lake Michigan and also stumbled across a beer garden.
SEE: Chicago Theatre
My mission was purely to take a look at the exterior of this gorgeous theatre. This Chicago landmark has been around since 1921 and has been an unofficial emblem for the city ever since. If you want to do more than just take a photo, you can also get tickets to see one of the events (mostly comedians or musicians), or do a tour of the venue.
SEE: Take A Picture By The Bean
Located in Millennium Park, Cloud Gate, or “The Bean” as it’s most commonly known as, is one of Chicago’s most photographed landmarks. The Bean is a relatively new tourist attraction to Chicago and is only 10 years old. Never the less, at all hours of the day you will find people hovered around this shiny display of art looking to snap the perfect picture.
SHOP: The Magnificent Mile on Michigan Avenue
A great and free thing to do in Chicago – take a walk down magnificent mile. It’s one of the best know areas of downtown Chicago. The mag mile is 13 blocks that stretches from the Chicago River to Oak Street and is lined with shops, restaurants, and beautiful buildings.
STAY: Accommodation is a little tricky in Chicago!
I tend to stay at Air BnBs when I travel. However, in Chicago, the state has an extra tax on Air BnB and it was almost the same price as a hotel. And in most cases, the locations were a little bit north or out of the city. We stayed at a hotel right in the core of downtown Chicago which was....wait for it.....a block south the Magnificent Mile! #winning!
We stayed at the Inn of Chicago which is an older boutique style hotel at a great nightly price. The service was exceptional and the location was exactly what we wanted. We were able to walk to most of the places on our list as well as there were restaurants and local transit at our doorstep. I highly recommend that you stay in the downtown Chicago area. Even though we rented a car, we were still able to move around on foot to fully enjoy our stay.
Word of Advice: The parking fees in Chicago are really high! You might want to download the app "Spot Hero" to help you find affordable parking in the city.
Chicago is now one of my most favourite cities to visit and I cannot wait to visit again! It was definitely a trip to remember and I am super excited to return to this legendary "Windy City".
With Love | Nikki xo