Chicago, Illinois
There is no such thing as a perfect trip but this getaway to Chicago was pretty close. We took in so much and I honestly don't know where to start or how to split all of our experiences into one blog without babbling but since Chicago was that good, I want to provide as many details as possible. In true T | R | E fashion, I will split the updates into a few different blog posts all of which will be tagged, related, and linked at the end of this primary post. If there is anything I forgot, look out for future posts about this trip since there are so many details to share.
Let's start with the travel!
Direct flights from CLT --> ORD is scheduled to be a 2 hour flight. We actually arrived 30 mins early to O'Hare. One thing to note & my research failed me on this one. If you are heading downtown, there is a 35-45 min drive from this airport, however there is another airport closer to downtown that is closer called Midway International. It's smaller in size but if you wish to beat the traffic, this maybe a better option if heading downtown. We decided on a ride share and while the airport is laid out pretty well, finding the ride share locations was a little tricky. We had to actually exit the main area for baggage claim and walk outside to another section of the airport to wait for our Uber. It's important to note where you are by section letter and color assigned because you will need to enter the information to book your ride and be located by your driver. Once we figured that out, we were on our way. We traveled early morning during peak hours (8:30 am), so a ride to our hotel was $40.00 one way. Traffic was heavy.
We stayed at one of my favorite brand of hotels and was perfectly situated near the sights of the city and the waters of Lake Michigan. We did a lot of exploring on foot and the location of the hotel, made it easy.
We booked a king room - and honestly at 377 sq feet, I was slightly nervous about the size but I actually was spacious enough for us.
There are several plans to choose from and some even come with a Lakeview but those also come with a different price and we were fine with the city view for this trip. I was really close to booking the Suite which gives ~700 sq feet but for such a short trip, we didn't need that much space as most of the trip would be spent away from the room anyway.
Things I love about the hotel:
Customer Service = Exceptional
Ease of Checking-In & Checking-Out
Central location to the city sights, dining + Navy Pier
Starbucks in the Lobby
Rooftop Bar - Streeterville Social
Spacious Lobby with seating, hightop tables, & plenty of charging outlets
Keypass required for elevator access (Safety was never a concern)
Fast housekeeping services (towel requests, etc.) during the pandemic
Not sold? Take a look at the other Chicago hotels and save up to 30% off through our partnership with Trip Advisor.
After dropping off our bags, we hit the ground running, well walking. We did almost 10 miles on foot in one day but it was worth it. I tried to plan everything but of course the plans were adjusted. We decided to head to the pier and on the way, we saw the boat tour planned for Friday boarding so we went for it. It was perfect timing. We already knew we wanted to do an architectural tour so doing it on the first day was a great idea actually. We were able to tour the city on the Chicago River and learn about the architecture of the skyscrapers, hotels, and landmark buildings. It was fantastic!! I highly recommended this tour. We booked with Shoreline Sightseeing & for two tickets, it was ~$90. Well worth 75 minutes & the bar on board was a plus. There are several boat tours & boats to choose from but we wanted one that had open seating on the top floor so that's one of the other reasons we choose this option. Did I mention, the bar on boat was an added incentive. 😊
The boat returned to it's departure location - Navy Pier. If you have never been to this pier, it's a definite MUST DO. It is on Lake Michigan and is coveted with shopping, places to eat/drink, docks for boat/cruise tours, a mini amusement park with a Ferris wheel, fair swings, and even a children's museum. It's here where we caught the beautiful sights of the skyline backdropped against the Chicago River, Lake Michigan, the cutest beer garden ever (yes - this is a thing), and caught some live music shows. The view from the pier never got old. During our trip, we walked here every single day and passed the time away.
The best views of Chicago are obviously seen from a few thousand feet in the sky. There are a few options but we opted for the John Hancock building. It was included in our City Pass (click here to get 5 attractions for $109 per adult, $89 per child to save $49%) which we buy when visiting cities to save money on bundled activities. 360 Chicago is located at 875 N. Michigan Ave. You enter through a lower level (not the main building entrance) to reach the elevators for the 94th floor. Once you head through ticketing (with our city pass, we were allowed to skip the line, even though there was no line, lol), they take a photo of you with a green screen with 3 background options available for purchase. Once upstairs, the view is absolutely breathtaking. You literally have a 360 degree view of the city and Lake Michigan. Thus far, this view is unmatched.
Here at the observatory deck, you also have Bar 94. What better way to take in the views than a cool cocktail in hand. I went for the Sky High Cocktail ($12.00) and it was the perfect pick. Timed perfectly, we wanted to see the city during the day, watch the sun go down, and then see the city light up at night.
We sat near the windows and waited for the sun to set. Absolutely magical.
After the sun went down, it was time for me to make another important decision - to TILT or not to TILT? You will never know how stressed I was somewhere between YOLO and hanging yourself over the side of a skyscraper is not the best idea. Well, I decided to go for it and a huge surprise, Thomas decided to do it also. Why is that a big deal? He is absolutely terrified of heights. I mean this man takes alternative routes to avoid driving over small bridges so yeah this was MAJOR. Since we waited so late, we ended up being the only 2 on TILT. I'm not going to lie, I was scared (he was too, lol) BUT it was over quick (1 MIN) and I must say it was worth it.
Welp, that's the top 3 for me but please continue to my other posts to see what other experiences were had. I think Chicago has replaced NYC as my yearly go to but I may have to find a way to fit in both. I'm allowed to be in love with multiple cities, right? 😉
I love Chicago!