Summer in the Windy City - A Beginner’s Guide to Chicago

Editorial Manager

Chicago was one of the last major travel hotspots in the US that had eluded me on my frequent trips across the Atlantic. After recently spending a week in the biggest city in the state of Illinois, however, I found a destination full of history, culture, incredible cuisine and great people. Here’s everything you need to know before planning your own summer visit to the Windy City.

First of all – and something I only found out by casually talking to one of the locals – the city gets its nickname from an unexpected place. Like many, I assumed the gargantuan Lake Michigan which runs along the length of Chicago (and beyond) was the source of the moniker. By all accounts it does get blustery in winter here, but that’s not where the name comes from.

A former politician from the city made a name for himself by verbally blowing hot air in Washington DC and so the name stuck. Chicagoans take it all in good spirits, much like everything else that gets thrown at them. From the way their sports teams perform to the hearty food they serve up, there’s an acknowledgement of their own status in the modern American zeitgeist which is charmingly honest.

Chicago is different from other American cities I’ve visited, and I think it might be one of my favourites. I had previously fallen for the popular misconception that Europeans will only enjoy US cities if they fall on either the eastern or western seaboard, but Chicago is comfortably somewhere in the middle.

The skyline of Chicago

The Downtown area is full of skyscrapers that many believe make for a better skyline than the one found in New York, and I’m inclined to agree. Newer neighbourhoods have a cool vibe that offer great food and drink without any of the pretentiousness I’ve found elsewhere in ’up-and-coming’ districts in the US.

Where to stay in Chicago

Head to one of the neighbourhoods if you really want to get under the skin of the city. I picked the West Loop where new restaurants, bars and coffee shops seem to be popping up every other week. The area is a 30 minute walk from the heart of downtown with the Time Out Market being one of the central points of interest. The Emily Hotel can also be found here, and its where I ended up staying for my trip to Chicago. Tying in the strong film heritage of the city to my hotel, Rooftop Cinema Club is hosting a residency at the property this summer and I happened to walk into a screening of ‘Mama Mia!’ when I arrived. Luckily everyone was listening to the film via wireless headphones as I’m not sure I could cope with a crooning Pierce Brosnan murdering an ABBA classic having just landed a few hours earlier…

Rooftop Cinema at The Emily hotel

The hotel falls in the Fulton Market district which is a tight collection of local eateries and high-end restaurants. On my first night I dined at the Fora within the hotel itself, but wanting to explore a bit more as I got comfortable with the area, I spent the next evening in The Oakville Grill & Cellar. The service here is relaxed, and I mean that as a compliment. You get to savour the excellent Italian-infused cuisine and soak up the atmosphere of one of the coolest parts of town.

Room rates at The Emily Hotel start from $309 per night

Set Jetting in Chicago

One of my favourite TV shows of the moment is the heart-pounding drama The Bear. The week I travelled to Chicago coincided with the launch of the second season of the food-centric series, and as the action is primarily set in the city, I knew there would be a certain amount of set jetting and trips to local restaurants on my schedule. I also knew that Christopher Nolan used the location as a stand-in for his version of Gotham City in the Dark Knight trilogy, so I had done a lot of planning before I even got on the plane for the 9 hour flight from London.

This street was used for several scenes in The Dark Knight

If you’re worried about missing out on posing like Batman, fear not. The Downtown area is dominated by buildings and avenues that feature extensively in the superhero series of movies. Head to South LaSalle Street, part of the Financial District, for the most iconic views from the cinematic universe created by Nolan. You also can’t miss the network of underground streets and elevated train lines that connect the city, both of which have featured in countless big screen outings from While You Were Sleeping to Planes, Trains and Automobiles.

The Bear recently featured one of its main characters getting a better understanding of Chicago via an architectural river cruise, and I can also heartily recommend this as a great way to get your bearings and learn more about the construction of the city.

The real beef sandwich shop seen in The Bear

Another great film to watch before travelling here is sci-fi thriller Source Code. This Jake Gyllenhaal movie opens with luscious shots of Chicago and features a notable landmark throughout. To cap off you trip in style, be sure to take a closer look at O’Hare, the international airport, which I figured out was the location where the McCallister clan lose one of their own in Home Alone 2.

Things to do in Chicago

I’d recommend starting with the aforementioned architectural cruise to really get a sense of the city. One of the benefits of doing this in the summer is that you can stay on the top deck and get to see all the remarkable buildings that have shaped Chicago. The history imparted by the guides is also funny and informative, all making for an excellent morning activity if you want to avoid the heat that creeps up on you later in the day. Try the Chicago Architecture Foundation Center River Cruise for what is widely regarded to be one of the best and most topical experiences available.

Another reason to visit Chicago in the summer is the chance to try authentic BBQ and listen to country music. The city isn’t best known for either, but when the Windy City Smokeout rolls into town you’re going to get a real Midwest show.

Millennium Park is another great outdoor destination to head to if the weather is good. To be honest, I was going to go here no matter what the conditions were as this is the location of Sir Anish Kapoor’s award-winning sculpture Cloud Gate. Better known as ‘The Bean’, the smooth metallic structure has become one of the most famous icons associated with the city but if you head here early in the morning you can get those social media photos you’re after without anyone else ruining the shot.

Chicago deep dish pizza is like no other pizza in the world. Italians would scoff at this gooey pie going by that name, but it’s the way locals like it. Swimming in grease, cheese and tomato sauce, you can’t really call this ‘a pizza’, but you can call it delicious. I’m sure it’s pure comfort food during the harsh winters, but it’s also great in smaller portions for a summer snack. Chicago-style hot dogs are the other local dish you have to try, but the particularities of this one are quite specific. Official ingredients are: a beef frank, mustard, tomato, pickle, relish, onion, sport pepper, celery salt… But never ketchup!

Following a busy day you will probably want to chill in the evening. Summer nights are an ideal time to check out some of Chicago’s blues bars and Rosa’s Lounge has a great reputation and vibe. It’s a little rough around the edges, just like the city itself, but its home to some wonderful live music.

With the weather giving me ample opportunity to hang out by the river, I went back there on another morning to take a guided kayak tour with Urban Kayaks. You don’t need any experience, but a little muscle is recommended. This was a great way to retrace some of our steps from the river cruise and work off the excesses of the previous night. Those good intentions won’t last for long if you end up at Beatnik on the River, a delightful brunch spot that has stunning views and a menu full of hearty dishes from around the world. Great cocktails too if you’re up for some day drinking.

You’ll certainly eat well in Chicago and another recommendation is Cebu over the other side of town in Wicker Park. The Violet Hour offers an excellent nightcap and harks back to the speakeasies you picture from the days of Al Capone and Elliot Ness.

Having spoken about the skyline at length, I couldn’t leave without going to The Ledge at Skydeck Chicago. Once the world’s tallest building, the Willis Tower (previously known as Sears Tower) has undergone a major revamp and is now an excellent attraction if you don’t mind heights. The protruding glass boxes give you unbeatable views, whilst film fans can also go to a marked area where Ferris Bueller spent part of his day off.

There’s a calmness here that caught me off guard. Expecting to find the same rushed energy of New York or London, the pace of life here is a pleasant surprise. In fact the only thing that seems to genuinely annoy Chicagoans is the addition of ketchup to hotdogs. Rest assured, you absolutely don’t want to be caught asking for that condiment here…

For more information on what to see and do on a city break here visit Choose Chicago

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