When the temperatures drop in Kansas most people are ready to fly south – not for this girl! Although I would have preferred the sunshine and beaches, Chicago (the Windy City) certainly blew me away this February (pun intended).
I spent weeks prior scoping out food to eat (my favorite hobby), sights to see, and where I’d lay my head to rest at night. It was a combination of birthday celebrations, romance for Valentine’s Day, and a much needed getaway that inspired this trip. I’m a bit of an over planner and for this trip I tried to let fate take the reigns – and that it did! A small list of the places I picked evolved as soon as we arrived (some for the best, some not so much).
Being there during the week (and in chilly February) meant shorter lines and fewer crowds. In 72 hours we saw the main sites and ate at some of the highest recommended (and even hidden) locales. Keep scrolling for a bite of Chicago!
Day 1 – Arrivals, Check In, and Dining
Our journey started with a quick, nonstop flight from Wichita. United and American Airlines have multiple nonstop flights there and back – just 2 hours each way (heed caution on airline prices with the new basic economy fares)!
Once we arrived we took an Uber to our hotel – the Renaissance Chicago Blackstone. The hotel is currently undergoing renovations to become a member of the Marriott’s Autograph Collection (We will be returning in the Spring for a follow up on the new brand). Located right on Michigan Avenue we were a short walk away from theatres, museums, parks, and many popular restaurants. Bus stops, trains, taxis, and Ubers are also right outside the doors at all hours.
The historic hotel first opened in 1910 and was named after Chicago rail tycoon Timothy Blackstone. Over the years they have hosted well known business and political figures – including Presidents Eisenhower and Kennedy. The facade of the building is reminiscent of the history it has seen. Through the lobby the classic Chicago feel continues. The rooms, however, have reached the new age with modern features and views of Michigan Avenue, Navy Pier, and Willis Tower. Aside from the views, the bathrooms really steal the show! Trendy wallpaper that might make one a little dizzy, bright lighting (and a make up mirror!), and a glass walk-in shower. After we unpacked, we explored the hotel’s breakfast room, bar and lounge (Mercat a La Planxa), and grabbed a quick coffee at the on-site Starbucks.
Our midday flight and unpacking left us hungry and we knew we had to visit one of Chicago’s most famous restaurants – Giordannos. A 10 minute walk from the hotel is one of the 16 locations, also right on Michigan Avenue. Known worldwide for the cheesiest pizza and my personal favorite, the Chicago deep dish style crust. The crust has a sweetness like my grandma’s homemade pie crusts while having the buttery and savory flavors of everybody’s favorite pizza. 
One more block south and beer afficiandos can find Vice District Brewing. The Valentine’s brews were on tap – a nutty V – Day Brown, a blonde Pleasure Trip, and for the porter drinker with a sweet tooth – the Choco Porter. Dog lovers will appreciate the pup-friendly venue and possibly make a new (furry) friend. If you’re allergic to dogs or maybe you prefer cocktails over brews – we recommend heading just past the North Loop to The Green Door Tavern. Don’t stop just here though! Head to the back stairs and look to your right – that’s correct. The bookshelf – or is it? Hidden on the shelf is a secret doorknob and just on the other side is a speakeasy (no password but a $4 cover) called Drifter. Order a hand-crafted cocktail served by the stylish bartenders and wait for the show to begin. Every night they host local entertainers. Our night began with a burlesque dancer and was capped off by an angel singing the blues.
Day 2 – Attractions, Views, and Small Bites
We started our morning with the continental breakfast at the Renaissance and a caffeine boost at the Starbucks. Even though it was during the week we did not take any chances and arrived at our first stop by 10am – the Museum of Science and Industry. Another world famous site in Chicago we were surprised to find no lines. Should you arrive and find a line you can skip the admissions desk and do a self ticketing kiosk. Make sure you add the U505 Tour to your ticket! The large size of this museum is filled with exhibits – both permanent and rotating so expect to spend at least an entire day here. We had been previously and still spent about 4 hours exploring. Some of the most popular exhibits include Chicago in Miniature, the U505 German Submarine, and Colleen Moore’s Fairy Castle. Our favorite exhibition during our visit was the Juried Art Exhibition featuring Black Creativity. MSI hosts the longest running exhibition of African-American art right in the city of Chicago. You can learn more HERE and we have included photos of our favorite works.
If you’re looking for more fun to fill your afternoon make your way to Museum Campus. The Adler Planetarium, Field Museum and Shedd Aquarium are all within walking distance of each other and located on the shores of Lake Michigan. The grounds provide great views of the city and surrounding shoreline. We chose to finish our day at the Shedd Aquarium . One of America’s top 10 for aquatic adventures this aquarium opened in 1930 and has a three story Oceanarium. Along with the variety of exhibits the history and architecture are widely fascinating. Learn the history of John G Shedd HERE. This time there was a short line but they try to make it fun while you wait by having your photo taken when you arrive. Travel through the Amazon, dive deep into the Coral Reefs and Caribbean, and catch a show at the Oceanarium. Our afternoon visit was less than crowded and afforded us unique experiences with the keepers who helped point out those little creatures in hiding!
Another long day of adventures meant we needed more fuel but we had one more stop that couldn’t wait – the view from Willis Tower’s 103rd floor and the Skydeck. We’re sure you’ve seen the videos of visitors stepping onto the glass ledges that hang 103 stories above the city but the videos and photos don’t do it justice. We recommend going at night for sparkling views that extend for miles.Getting up is the easy part and waiting in line to get back down takes longer. On the way to the elevators you pass through a museum that details the history of Willis (previously known as Sears) Tower and includes fun size comparisons. How many of you would it take to reach the top? Based on the average human height, it would take approximately 307 people to reach the top. We’re not big fans of expensive souvenir photos – but this time we bought them all!
Once we wrapped up our tour and strolled through the gift shop it was time for that fuel we desperately needed. This time it was my choice and I knew before we arrived in Chicago there was a place I had to go – Chinatown. All my life I had dreamed of Dim Sum (Wichita sadly, has none that I am aware of – let me know if you find sum! HA!). We went to one of Chicago’s Top Rated (and highly recommended by friends) MingHin Cuisine. Late night Dim Sum served traditional style (minus the cart). Since this was our first time we went all out – our waitress looked at us with wide eyes and said “WOW!”. We asked if it was a lot and she said it was – we dared to continue though. Tea was sipped while we waited and then our table was filled with Shrimp Dumplings, Siu Mai, BBQ Pork Buns (My favorite!), Country Style Dumplings, and more. Afterwards we wandered the hidden alleys of Chinatown and located the infamous sign. Take the time to wander here during the day too for sights, shopping and of course – more dining!
The best end to our day was another trip to a speakeasy – although this one was more laid back and albeit – less hidden. The Watershed is another bar within a bar. Make your way to Pops for Champagne, head to the back stairs, and at the bottom is Watershed. A quiet bar with local brews, crafted cocktails, and daily drink specials. Find yourself at the bottom of a glass of one of their 50+ beers and sink into their comfy booths.
Day 3 – Breakfast, Arts, and Parks
The small breakfast at the Blackstone is a great quick start to the day but if you’re like me you need a breakfast designed to fill that 8:00am bellyache. Leave your bags with the front desk (if you’re checking out like us) and get your forks ready to dig in at the Chicago Waffles. Having heard about their waffle flight I was determined to try them all – Chocolate, Red Velvet, Green Tea, and Leige. Upon arrival though I made the mistake of still looking at a menu. I love a good Eggs Benedict and they had Eggs Benedict…Waffles. Two Leige style waffles topped with pulled pork, poached eggs, and Hollandaise. I couldn’t say no – and I also didn’t say no to the waffle flight. The plates filled our table for two and barely left room for us. It’s a good thing our next stop was only a few blocks away because we waddled out of there!
When passing the various parks and buildings on Michigan Avenue you’re sure to notice the artwork along the way. At the end of Grant Park you’ll find “Agora“. There are 106 headless walking sculptures here. Continuing on towards Buckingham Fountain you will find towering flowers made from old car parts like doors, hoods, etc. The Buckingham Fountain is also a work of art itself and makes for a lovely backdrop with the city skyline for photography.
We kept walking until we reached the Millennium Park and found the famous, shiny, BEAN! Its real name is Cloud Gate. Fun Fact: Sealed inside the sculpture is a wooden frame and office space/workshop. Items from its working days still remain inside – like a time capsule! By this time the weather was in the 50s and this meant everybody was out for their photo-op and selfies. Snap your photos and head to Cindy’s Rooftop Bar (recommended by locals) for a quick bite and stunning views of Millennium Park and stretching all the way to the shores – you can even see the Museum Campus!
Now if you’re feeling really energetic you can keep walking – or you can catch the nearest Taxi, Uber, or Lyft over to the Navy Pier – shopping, dining, sights, a few fun rides during the warmer months, and even a Shakespeare Theater. Watch the latest blockbuster films at the AMC IMAX. You can also catch a few boat rides along the shore. Margaritaville has a walk-up-to-order so you can take your margarita (or beer) along with you while exploring. If you’re bringing the little ones you can stop at the Children’s Museum for a fun filled, hands-on day. In 2017 the Navy Pier is celebrating 100 Years and there are 100s of on going events (not directly related to the 100 Years). From food features, fitness classes, Art & Music Exhibitions, and even more Theater and Dance performances (new additions to the theaters and art centers). Make sure you go inside too! There are shops, attractions (Mirror Maze), and World Famous Chicago Style Hot Dogs inside. Plus a lovely atrium with tropical plants and fountains!
All this walking sure wore us out – our last visit was to America’s Dog for a Chicago Dog (had been previously dragged through a garden) and a Dallas Dog (chili, cheddar, and onions) before making our way back to the hotel for our belongings and heading to the airport.
If you’re ready for a quick weekend getaway or even feel like spending a week – Chicago can be done both ways. We didn’t make it to all the sights so we know we’ll be back. We didn’t eat all the food so we know we will come hungry. Most importantly though we’ll be ready for more adventures!
What’s your favorite weekend getaway?
Author – Angie Courtney
Sunflower Travel Staff
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