Chicago, known as the ‘Windy City’ is ‘wow’! I know that maybe not be the average way to describe a city, but it was the word I repeated all day long. I was like a broken record! Every street corner, every direction I looked, I was blown away by the beauty the city has to offer. My neck began aching as I constantly stared up at the tall, high-raised buildings. It’s just incredible. Maybe because I come from a city without a single skyscraper. Maybe because it was the first city I have travelled to since pre-pandemic? Or maybe because it’s just one incredible city! A city I never forget!
We only had 48 hours in the city as we were about to embark on a journey of a lifetime. Yes, you’ve guessed it! We were there for Route 66, the Old Mother Road!
To be fair, we found 48 hours enough time in the city. I’m not saying we saw everything the city has to offer, far from it. And certainly not possible in the short time frame. But we saw what we wanted to see. You know, the touristy spots that people travel for. Or what I call the city highlights.
Getting Into/Around The City
My first tip is, do not bother with a car. Just not worth it! The city offers good transport links, a lot of the city can be seen on foot or on bikes, and parking is very expensive.
To get to and from the airport there is a train which will take you to the city centre. At the time we visited, it cost just $5 for a single ticket. You can pay at the airport or order one through the app, Ventra. If you are planning on using the trains a lot while you’re in Chicago, it might be worth buying a 3-day pass, at a cost of $15. Remember, the pricing is from the time when I visited in May 2022.
Getting around the centre of Chicago is easily done on foot. Most of the main attractions can be walked to. There are bikes and electric scooters, which you can hire. If you are wanting to travel a little further out of the city centre, there are good links to buses and trains.
Where Did We Stay?
We stayed in the Club Quarters Hotel, in Central Loop. This is one of the main areas of Chicago! The Loop is downtown Chicago. The hotel was ok, nothing fancy, but clean and in a good location. What more do you need?
Staying in the Loop is more pricey because it’s in the centre of Chicago. Most of the attractions are within walking distance. If you want something more on a budget, I recommend avoiding the central loop, but somewhere that is on a good bus or train route.
My ‘Must Visits’
As we were only in Chicago for 48 hours, we didn’t have a chance to see everything the city has to offer. Here is what we did visit, and what I recommend you should visit on your trip to the windy city.
Buckingham Fountains
Buckingham Fountains, located in Grant Park are beautiful. They are known to be one of the largest fountains in the world!
They only run part of the year, from early May to mid-October. So if you visit in winter, you probably won’t see them in action. Every hour, from dusk to 10 pm, they perform a lovely light show to watch.
Route 66 Sign
If you’re just about to start the famous historical Route 66, getting your photo snapped at the start line is a must! The sign is located down E. Adams Street, not too far from Millennium Park. If you are driving Route 66, I recommend getting a photo of this sign when you walking around the city, and not when you’re starting the route. It’s a busy road, and parking can be very difficult! Also, the time of day can make a difference to your photo.
Here’s a photo that was taken mid-afternoon:
Here’s a photo that was taken early morning:
Millennium Park
This has to be one of my favourite spots in Chicago! It’s such a beautiful park, full of creative work, surrounded by the impressive city skyline.
Millennium Park is not a massive park, but it does get very busy, making it difficult to capture good photos. My advice is to there either first thing in the morning or visit later in the evening.
Here’s a photo of the Bean taken mid-afternoon:
Here’s a photo of the Bean taken first thing:
Here are some of the things to look out for in Millennium Park:
Boat Trip: Wendella’s Lake and River Architecture Tour
This trip is a must! It was just incredible from start to finish! You get to travel down the river, passing through all the incredible skyscrapers, and see all the different architecture. You then head through the loch gates and onto Lake Michigan, where you are treated to incredible views of Chicago’s Skyline.
The boat trip was 90 minutes long. We booked ours with Expedia before we flew out to Chicago. You can book it on the day at the ferry port, but I recommend booking in advance as they can sell out.
Navy Pier
To be honest, the Navy Pier wasn’t my favourite attraction in the city. If you are short of time, this is one I would say you could miss out on!
The Navy Pier has a Ferris Wheel, food places, entrainment, and views over Lake Michigan. If you are not doing the boat trip, then yes a walk down Navy Pier is definitely worth it. However, if you’ve done the boat trip, you are likely to be treated with similar views of Lake Michigan again.
Magnificent Mile – Starbucks
The Magnificent Mile is famous for being one big shopping street, cool restaurants, posh hotels, and home to the world’s largest Starbucks! Yes, you’ve guessed it, we had to stop at the Starbucks! The street travels from the banks of the Chicago River to the south, to Oak Street to the north. It’s one long road!
Walking down the Magnificent Mile is a ‘must’ when in Chicago. But while you are walking down it, make sure you stop at the Starbucks Reserve Roastery. A 5-story high Starbucks, that sells of cause coffee, lots of lovely food, and there’s even a Cocktail Bar if you fancy something a bit stronger.
Visit Ed Debevic’s Dinner
If you fancy something a bit quirky for dinner, I recommend Ed Debevic’s, located just off the Magnificent Mile. They do delicious burgers, in a 1950s-style American dinner. Just one thing tho, expect the staff to be rude! Don’t worry, they are rude on purpose. It’s basically the waiters acting. They will tease you, joke with you, and make you laugh! It’s certainly a great experience!
The Chicago Theatre
When in Chicago, you have to see the Chicago Theatre, all lit up in the evening! Built-in 1921, it really is something! I would have loved to have seen a show, but there wasn’t anything I fancied at the time I visited.
To find the Chicago Theatre here is the address: 175 N State St, 60601
Willis Tower Skydeck
There are two viewing towers in Chicago: Willis Tower Skydeck and 360 Chicago. Willis Tower Skydeck has the glass ledge to stand on and 360 Chicago has the tilting glass. We personally decided to choose Willis Tower Skydeck over 360 Chicago, as I preferred the idea of standing on a glass ledge, instead of being on something that leans out. It was a personal choice, either seem good to do. You can do both, but again a personal choice, we decided to choose just one as we thought the other would provide similar views of the city skyline.
We booked our ticket to go up Willis Tower Skydeck before we visited via their website, as they can sell out if you wait till the day. At the time we visited, we had to book a time slot. We paid more for the Skydeck Expedited Entry. This ticket allows you to get fast-tracked. However, we soon realised on our visit, that we didn’t need to pay extra as there were no queues for the general entry.
Here is a link to their website: https://theskydeck.com/
The visit to the Skydeck was great on a whole. However, one thing I did find a little disappointing, was the time you had on the glass ledge. You basically get given a minute on a timer. So you quickly have to snap away with the camera. As soon as the minute is up, they chuck you out of the ledge and put the next a lot of people in it. This is the same for either type of ticket you’ve purchased too! However, on the Skydeck itself, there’s no time limit up, it is just the glass ledge.
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Further Reading
My book, How I Tamed the Wolf, Living with Lupus is available on Amazon via this link:
https://www.amazon.co.uk/dp/B09M73X2JQ/ref=cm_sw_em_r_mt_dp_MWAF58981F0VVMNRV1WN
Other travel guides you may like:
Miami – https://livingwiththewolf.co.uk/miami/
New York – https://livingwiththewolf.co.uk/new-york/
