When planning my travel month, there were a few places I was willing to compromise on, and skip if I didn’t have the time. Chicago was not one of these places. I was determined to go, and now I am so glad that I did. Here is how I would spend one day in the Windy City
9am: Wildberry Pancakes & Cafe
Wildberry, right on the North edge of Millennium Park, is definitely not the cheapest breakfast to be found in the city; but it’s filling, well-made and downright tasty. I had the Los Altos Benedict – with chorizo, roasted peppers and a delicious chipotle hollandaise – but every plate of food that came past me looked amazing. You know you have made a good choice when your choice is incredible but you still get major food envy for every meal that passes you by. I haven’t tried it myself, but if you are looking for something a little sweeter, then the caramel-apple-pecan French toast looked especially good, as did the signature ‘berry bliss’ pancakes.
10am – Millennium Park
Why not burn off some of those (many) breakfast calories with a brisk stroll through Millenium Park – where President Obama made his commencement address in 2008. It’s a beautiful and vibrant place to take a walk, especially in the summer and early autumn, and because it’s attached to Grant Park you can make your walk as long as you would like to. The obvious stop is the Bean (or Cloud Gate as it should be known) – the 20m reflective bean that allows for really interesting, warped views of the city. Millennium Park is also home to the Jay Pritzker pavilion which hosts annual free events, such as the Chicago Jazz festival, the summer film series and the Chicago blues festival, from within it’s unique, futuristic bandshell. While you are here, why not also head to the Chicago cultural center? It’s located right by the park and is also home to many free events – as well as beautiful architecture like this amazing glass dome.
11am – The Lakefront Trail
It’s time to hop on one of the city’s many blue Divvy bikes – which you can use for unlimited rides of 30 minutes or less for $9.95 a day. It’s much more convenient than traditional bike rental because you only use the bikes when you need to, and you don’t have to worry about finding places to store them when you don’t: just make sure to plan ahead and decide which station you want to drop the bike off at so you don’t end up biking in frantic circles as the minutes tick down! Also keep your eyes peeled for ‘unicorn’ bikes – somewhere in the city are two red and one purple Divvy bikes and if you see one you should definitely take the opportunity to ride it. Chicago is a pretty bike-friendly city, and you can bike most of the way up the Lake Michigan shoreline – with Divvy stations as far south as 83rd Street and as far north as Northwestern University. Start at Millennium Park and bike as far north as you can before your legs get tired. Make sure to stop at Navy Pier and Lincoln Park to give your legs a well deserved rest!
12:30pm – Cheesie’s Pub
After biking for over an hour along the winding lakefront trail, you will almost certainly be starving and you know what kind of food group gives you the most energy? Carbs. Cheesie’s Pub and grill on West Belmont Avenue doesn’t just offer carbs, it offers carbs on top of carbs. Their mac and cheese grilled cheese with tomato soup dipping sauce is an absolute revolution of bread, cheese, pasta and gluttony. Pair it with a side of fried cheese curds, fried pickles or just fries and you will be back up and running in no time. If pasta in a sandwich seems a little excessive to you (and why would it), why not try the Popper – loaded with cheddar cheese, cream cheese, jalapeno slices and crispy bacon with a side of spicy chipotle dipping sauce.
2pm – Montrose Beach
If you are anything like me, a big lunch will make you very content, very sleepy and very ready for a lie-down. So, post carbfest, head to one of Lake Michigan’s many beaches for a sunbathe, a paddle, or even a full-on swim. There are so many beaches along the shore, but Montrose is probably the most popular and it’s definitely the biggest. If you are looking for somewhere a little bit less crowded, there are so many other choices: from Oak Street Beach to North Avenue Beach or Ohio Street Beach (if you are looking for a challenge, this is where hardcore triathletes practice their long distance swims). Even in the summer, the lake is pretty chilly, but there aren’t many things more refreshing than a quick dip in the open water.
4:30pm – 360 Observatory at the John Hancock Center
Expect huge queues at the Hancock Center – and I mean huge. You could be standing for at least 2 hours, so start preparing yourself for that mentally and physically now! I decided to get the ‘sun and stars’ ticket which meant I could go up twice for $4 more than the cost of a single ticket. That way, you can see the views during the day and night – but if you don’t have time for that, try and go up for sunset to get the best of both worlds. The panoramic views over the city are absolutely phenomenal, and (I can’t believe I am saying this) might even top those seen from Top of the Rock. That mixture of sprawling urban skyscrapers and shoreline is fantastic and the ‘Tilt’ attraction is an extra-special added bonus. If you haven’t heard of Tilt, check out this video and know that it still can’t quite do justice to how dizzyingly terrifying it is to be dangled 1000 feet over the side of a building. I can’t vouch for this, but apparently on clear days you can see 4 neighbouring states from the 360 Observatory. What I can vouch for is that the views are absolutely stunning and truly unforgettable.
8pm – Giordano’s
It’s time for – you guessed it – more carbohydrates! You just can’t go to Chicago without eating a deep dish pizza, and the pizza debate in the Windy City definitely rivals the one in New York. The two common contenders are Lou Malnati’s and Giordano’s and I ended up going for the latter – for no other reason than I was hungry and it was closer. Don’t go to Giordano’s expecting a light meal: some of their mammoth pizzas weigh as much as three pounds and are definitely made for sharing. If you are looking for a thick flaky crust, enough cheese to sink a small battleship, a generous amount of toppings (I went for the Chicago classic, with pepperoni, green peppers and mushrooms) and a rich red pool of tomato sauce poured on the top then Giordano’s is the dream. It’s not cheap – at around $20 for a small pizza – but even that size could easily feed two people. If you are on your own, take the leftovers home and your breakfast is sorted for the next 2 to 3 days!
Where to stay:
The HI hostel in Chicago is in a great downtown location right by Millennium Park, with rooms from $34 per night and a 24 hour lounge and kitchen area for if you roll up at 6am and your room isn’t available for 8 more hours, like I did… The whole hostel has a really friendly atmosphere, the staff are incredibly helpful and they offer free events (like comedy shows and walking tours) as well as discounts to local attractions.
How to travel:
Chicago is very bike and pedestrian friendly, but for longer journeys the L train can always get you where you need to go. All of the lines ‘loop’ around the city centre, making changeovers very easy and both airports (Midway and O’Hare) can be reached on the L (via the red and blue lines respectively). Each journey is only $2.25, apart from trains from O’Hare which cost $5, making it a fairly cheap and easy way to travel.
Have I missed anything? How would you spend a perfect day in Chicago? Let me know in the comments!