When visiting a city for the first time the list of things to do can be overwhelming, even travel books, which I am a huge fan of by the way, can tend to be too broad as they are trying to cater for every person, for every occasion and juggling sponsors. I have put together a list of what I think are the Top 5 things to do or see in Chicago, especially if you're having a whirlwind trip.
1. The Architectural River Cruise.
There are a few companies that operate from the Riverwalk by DuSable Bridge on Michigan Avenue that offer similar deals, so we spoke to our concierge to see if there was a deal he could offer us which lead to us choosing 'Chicago's First Lady'. I can totally recommend them, they give a full informative tour and are so friendly, as well as them using profits to support the Chicago Architecture Foundation.
Any of these tours though will be amazing, at the end of the day you still get to see the same things, it's just the information that may differ. It's a great relaxing way to truly grasp the magnitude of the buildings, learn a lot of history about the city, get a lot of information on the districts and get unparalleled views of the skyline from many different angles. The journey also takes you right out to Navy Pier and Lake Michigan which is hard to get a good view of from anywhere other than the river.
We were given a recommendation to do this tour and it turned out to be my favourite thing I did in Chicago, especially on a first visit to the city. If you're visiting in Spring or Summer too it's a great way to get a tan, but make sure to where sunscreen because I got a nice burn to start off my trip. I will be doing a full post featuring many more images from the tour in the next week or two.
2. Lake Shore Drive.
Driving at about 50 mph it's hard to get a clear shot, especially through a car window, but trust me it's beautiful in summer!
This is something I didn't read in any of the guide books before going to Chicago. We were lucky enough to have a friend of a friend who offered to show us the 'real Chicago' which lead to us seeing Lake Shore. I would recommend this mostly for those with a car as we were picked up by our friend, however if you set aside the day to stroll along it is definitely worth checking out too. There are so many of the actual sights you will hit along Lake Shore Drive including, Millennium Park, Navy Pier and endless views of the city, but for me it's worth it to see a whole other side of Chicago, the beach.
The beaches are small yet beautiful on the lake, but on the lakes its not about the sand, it's about the boat's. This was my favourite thing to see that I did not expect, while you're on the river you see a handful of parked yachts and a few travelling up and down but when you go to the Lake you see where all of them come to play. They gather together almost covering the water so you could walk from boat to boat and relax or party all day. It's something that most tourists wouldn't head to and a real part of Chicago life especially in the summer.
Not only this though it's a great place to start to see a lot of what the city does have to offer with the chance to come across some hidden gems and beautiful views. Maybe even catch a Segway tour or have a snow cone in a storm like we did.
3. Go to a Rooftop Bar/Club.
Of course one of the many things listed on every list of 'things to do in Chicago' it says to go to the viewings decks of either the Hancock Building or the Willis Tower, these are both amazing, but more expensive to do and also a hot tourist spot. If you head to one of the cities roof top bars, it's normally free to go up, unless you have to pay entry to the club, but then it's two for the price of one and you get to party with the view not just look at it.
The nature of a place being roof top, also tends to mean it will be a pretty high end affair. We chose to go to ROOF at theWit and it was amazing. The views were amazing but the vibe of the whole place was awesome. Another benefit is the views are still incredible, they will be anywhere in this city, but you're far less likely to find these views on a post card. Although above I said the Hancock Building's actual viewing deck is expensive, another alternative is going to The Signature Bar at the top of the Hancock, to eat booking is essential and pricy, but to get to the 96th floor of Chicago skyline with no upfront fee is pretty cool, if you can go for sunset and just have a soft drink if you're on a budget, it'll be worth your while.
4. Wrigley Field.
Now this one is definitely more of an obvious choice, but one that's worth the trip. The baseball stadium is a little out of the main city meaning that you will actually get to see a little more of the 'real' Chicago on your trip there, we actually went as part our tour with a local friend. There is always something going on at the field and around the area, a huge official merch store is across the street and even the local Taco Bell wears a little Cubs hat. It's a great atmosphere all around the area and everyone is keen to talk to you and share how much they love their team.
5. Millenium Park.
The reason I left this one until last is because I don't think there is a 'must see in Chicago' list where this doesn't feature. Millions of dollars have been invested in to the park and development, out of sight I should say, is still going on so it truly is an oasis in the city. Within just the top left corner of the park it features, Cloud Gate or 'The Bean', a ridiculously impressive Jay Pritzker open air theatre, the Crown Fountain and Lurie Garden, all of which deserve a bit of time just really enjoy and take in the surroundings. All of this is free and breathtaking and will guarantee to give you a few classic 'I was here' shots.
On top of all of this there is constantly something going on throughout the rest of the park, a lot which is also free or pretty cheap. Whilst we were there for example, there was a blues festival and Romeo & Juliet was on at the open theatre.
Chicago is a fantastic city, probably one of my favourite I've been to so far in the world, if you stay within The Loop, you can just walk for about a 10 block radius and have weeks of things to do so just go out and enjoy it.