24 May 2019

A Long Weekend in Chicago: Bex's Guide

It's taken me too long to visit Chicago — the Midwestern city, on the shores of Lake Michigan, has been in my sights for some time. I missed out on a work trip a few years ago, but as it would have been during a particularly cold and snowy February, that may have been for the best.

I snapped up a good flight plus hotel deal on BA Holidays, arriving on a Friday afternoon and flying home late on Monday night, giving me three-and-a-half days in the city. As I had to pre-book so many restaurants and activities, my schedule was tightly packed and I wished I had stayed at least one extra day, so that I could have spent more time in the Lincoln Park and Logan Square neighbourhoods and visited the Field Museum. As for the weather, it was mixed; Friday and Monday were beautifully sunny and fairly mild, while Saturday and Sunday were grey, cool and intermittently rainy. As a recent episode of The Good Fight (a favourite Chicago-set but New York-filmed legal drama of mine) demonstrated, that's May in Chicago for you.

Downtown art and architecture. I chose to stay in The Loop so that I could be fairly central, but also because I wanted to explore the public art and architecture in the skyscraper-filled area. I loved seeing the mix of architectural styles, and watching the L train rumbling over the elevated railway tracks.

I took an architecture boat tour with the Chicago Architecture Center, an extremely informative and interesting 90-minute ride along the vibrant turquoise Chicago River and each of its three arms that hug The Loop. I learned that Chicago's 'Second City' nickname comes from the fact that most of the city had to be rebuilt after the Great Fire of 1871. Meanwhile, in the second photo below, the base of the shiny high-rise building (150 North Riverside) had to be designed like the base of a Kalita Wave dripper because of ownership of the land in the 'missing' segments. Unfortunately, my tour was on a cloudy day and my photos weren't great but I'd still highly recommend it.

I also spent a lot of time admiring the views from the Riverwalk and the various bridges, including the brutalist cylinders of Marina City and the grand, Spanish colonial revival Wrigley Building. The after-dark visual art projections on the Merchandise Mart, AKA Art on the Mart, were fun to watch too.

Millennium Park. My hotel was just one block from Millennium Park and I visited the 25-acre green space several times. There are several public artworks inside, perhaps the most famous being Anish Kapoor's Cloud Gate (AKA The Bean). I first visited on a sunny Friday afternoon when it was extremely busy, but took some better photos early on Saturday morning before my run (my leaping photo was taken by a kind fellow tourist).

Lakefront Trail. Chicago's 18.5-mile Lakefront Trail is another good way to enjoy the great outdoors in the city (weather permitting). I ran south to Northerly Island one morning, and north past the Navy Pier to Oak Street Beach on the other. Both routes yielded great views of the skyline and of the vast blueness of Lake Michigan.

360 Chicago Observation Deck. I like to visit an observation deck when I first arrive in a new city to help me get my bearings (cf Tokyo), and as the skies were clear on my first day, I decided to catch the sunset at 360 Chicago inside the John Hancock Building. If you don't want to pay for a ticket, you can go to the Signature Lounge one floor up, but there was a longer line for the latter and I was worried I'd miss the sunset. 360 Chicago wasn't overly crowded either and I took dozens of photos as the sun went down and the city's lights came on. The Willis Tower's Skydeck is another, slightly taller option for great panoramic views.

Hamilton: The Exhibition. I'm a huge fan of Lin-Manuel Miranda's insanely clever and engaging Hamilton, the musical about the life of US Founding Father Alexander Hamilton, which I saw in London last summer. When I heard that there would be an exhibition about the man, the history and the musical in Chicago during my trip, I knew I had to go. The tickets were, I would say, cynically priced but I spent over 90 minutes exploring the exhibition, which had many interactive features and impressive audiovisual displays. The Northerly Island location is a little inconvenient if you are sans car.

The Second City e.t.c. stage. A friend of a friend recommended that I try to get tickets for the e.t.c. stage of Chicago's premier comedy club rather than the main stage. And the show I saw, Grinning from Fear to Fear, was brilliant: by turns bitingly clever and surprisingly warm. The show includes two scripted sets, plus a bonus improv set for those who want to stay.

Logan Square. This leafy neighbourhood, six miles northwest of the downtown area, feels almost suburban in parts, with grand houses and plenty of green space, although there are also many cool eateries and bars. As well as exploring some of the speciality coffee in the area, I also enjoyed walking through the bustling Sunday afternoon farmers' market, which had produce, street food and live music.

For my speciality coffee recommendations for Chicago, check out this post.

When researching restaurants for this trip, I quickly realised that booking in advance was either necessary or crucial to avoiding a long wait — especially during weekend brunch slots. As such, I made bookings for many of the eateries below. Unfortunately, I was too late to get a table at one of the fine-dining establishments I identified, most notably Grant Achatz's Alinea (for which you purchase a pre-paid ticket for the multi-course tasting menu), but also The Smyth and Acadia. As you will see, I mostly ate in the meatpacking district, the West Loop, which is also an interesting area to explore if you like murals and street art.

Au Cheval (West Loop)
As soon as I read about this diner-style bar with its much-fêted burgers, I was determined to eat there, even though I'd heard that the waitlist could be over three hours' long at busy times. Somehow, I struck it lucky and walked right in to a seat at the counter (for prime viewing of the excellent hamburgerology skills) when I arrived just after 6 pm on a Saturday. I had the single cheeseburger (two patties with cheese) with bacon, rather than au cheval (with a fried egg). It was delicious: the burger was meaty, juicy and flavoursome. The staff were very friendly too. The advice I read suggested that mornings (arrive before opening) and early afternoons or very early evenings on weekdays were the best times to go to slightly minimise wait times.

If I hadn't got into Au Cheval right away, my plan was to go to The Loyalist (the cocktail bar at The Smyth) for a drink and nibbles. Instead, I headed over after dinner. It's a sleek spot for creative and expertly mixed cocktails.

Blackbird (West Loop)
Another legendary Chicago spot, Blackbird is famed for its bargainous $28 three-course prix fixe lunch, which is only available on weekdays. I had: shrimp confit with kohlrabi, chilli and cashews; chicken schnitzel with nori honey and pickled radish; and white chocolate lime mousse with almond, and lemon-verbena and strawberry sorbet. The flavour pairings worked perfectly, the food was beautifully presented, and the attentive staff gave great service.

Little Goat Diner (West Loop)
Top Chef winner Stephanie Izard owns two restaurants that face each other on West Randolph Street: Girl and the Goat and Little Goat Diner. I had a Saturday brunch reservation at the latter and promptly dived into the extensive menu of all-day breakfast and comfort food. Deciding what to order was difficult but I decided to go for the sweet onion brioche French toast with fried chicken, eggs, BBQ maple syrup and strawberries. I usually prefer savoury brunch dishes but this had just the right sweet–salty balance and was so good. Alas, it left no room for more doughnuts later on!

Roister (West Loop)
Although I couldn't eat at Grant Achatz's Alinea, I did get a brunch reservation at his casual eatery in the West Loop (casual, in this context, means just one Michelin star). The staff at Roister were warm and very welcoming and there was a relaxed atmosphere on Sunday morning. Somehow, I ended up eating fried chicken in various forms of three occasions this trip, but the fried chicken sandwich with hot sauce and chamomile mayo on the Roister brunch menu was brilliant. I perched at the 'hearth' bar where I watched the chefs at work, and the kitchen even sent me a complimentary dish: a refreshing mango, cucumber, peanut and mint salad.

Pacific Standard Time (Near North)
You know you're a jet lag pro when you've only just arrived from London into Central Time when you head right to Pacific Standard Time. This large, stylish restaurant focuses on creative California fare. You can opt for smaller, sharing plates or larger entrées. I had an avocado salad with blood orange and quinoa, followed by a strip steak, and accompanied by a very fine gimlet. They did also have pizzas on the menu, which looked great, but they weren't Chicago-style, and as I knew I probably wouldn't try a deep-dish pizza (not my thing), I thought it would be disloyal to eat another pizza style in the city.

Two Lights (Old Town)
Ahead of my 7 pm show at The Second City on Sunday evening, I needed to find somewhere to eat in Old Town. This proved quite difficult until I came across this new seafood restaurant, just opposite the theatre. The restaurant's décor is minimalist and beautiful, with a long, L-shaped counter at the centre of the action. I've visited the Maine lobster shack for which Two Lights is named and other than both serving lobster rolls, the two eateries don't have a huge amount in common. But the food, cocktails and service was all very good at Two Lights; as well as an excellent bourbon cocktail, I had a pan-seared halibut with mash for my main course, and it was lovely, albeit a little pricey given the portion size.

Lincoln Park. My favourite neighbourhood to shop was Armitage Avenue, a neighbourhood with pretty, historic buildings between Lincoln Park and Old Town. I was on an Allbirds and Marine Layer mission, but also enjoyed visiting some of the many independent stores in the area, such as Art Effect (fashion, accessories and gifts) and Top Drawer ('tools for nomads', i.e. lifestyle, homewares and stationery).

I also walked south to the area near the North / Clybourn L station, where I found a lot of my favourite US chains, like J. Crew, The Container Store, Banana Republic, Athleta and Anthropologie. The shopping experience wasn't particularly exciting, unless you like large parking lots, but it was convenient to visit a lot of my favourite stores in one place.

North Michigan Avenue. I enjoyed strolling along the 'Magnificent Mile' stretch of North Michigan Avenue — reminiscent of Manhattan's Fifth Avenue on account of the large department stores, high-end stores and grand buildings. Again, the shopping wasn't particularly interesting for me, although I did get another chance to visit J. Crew and Lululemon. I also enjoyed visiting my namesake: Walton Street.


For packing tips, check out my recommendations of tried-and-tested products for travel.

I stayed at the Fairmont Chicago, a large luxury hotel in the heart of The Loop, near Millennium Park. I usually prefer boutique hotels and had hoped to stay in the West Loop, but there was such a good deal on the BA Holidays website, that I went ahead and booked. My room on the 30th floor was large and comfortable with a nice city view. There's a small gym and spa in the basement and there are several eateries. I didn't make use of any of the hotel's other services, but I had no complaints about my stay and would recommend it to anyone wanting a high-quality, centrally located hotel.

Hoxton Chicago
Unfortunately, just after I'd booked my holiday, I got an email from the Hoxton to tell me their hip new hotel in Chicago was open for booking — and as it was their seventh site, they were offering rooms at $77 per night. As the Hoxton is located in the West Loop, this would have been perfect me; I really enjoyed my stay at the Hoxton Amsterdam and I've eaten and drank at both the London and Paris Hoxton hotels too.

Arriving and getting around...
Like most international travellers, I arrived at Terminal 5 of O'Hare. There was a bit of a delay getting us to the gate and I'd thought I could just hop on the L and ride into the city. First, though, you have to get to Terminal 2, and after following the airport signs to the trains, I kept hitting dead ends. It turns out that the transit between the terminals is currently closed and you need to take a small, ill-equipped shuttle bus to get to Terminal 2. I soon realised that the queue running the length of the arrivals hall was for the said shuttle bus. Eventually, I got to the L station and the blue line got me into the Loop 45 minutes later. Do factor the terminal change (15-30 minutes, depending on timing) in to your journey time.

On the positive side, you can pay with a contactless credit card or Apple Pay to use the L and local buses, rather than having to buy a Ventra card. The fare is $5 from O'Hare. I then added a three-day unlimited pass ($15) to my Apple Watch, which I used for the rest of the trip, including the return journey to O'Hare. I used the L a lot during my time in Chicago, as well as walking a great deal and taking the occasional bus when in areas poorly served by the train. As I was a little short on time, I did consider Ubering on occasions, but as I was travelling alone, I preferred to use public transport and save my money for cocktails.

Speaking of money, the currency is, of course, the US dollar, and during my trip, the exchange rate was $1.30 to £1, fairly similar to the dismal rates we've had for the past few years. I paid with my credit card — and increasingly with Apple Pay or contactless — everywhere, and only needed to use cash to tip hotel staff.

When to go...
For the best weather, May to October is the best time of year to visit. I'd hoped to visit in June or September, when it tends to be warmer than May, but flights and hotels were also more expensive. If you really like really cold weather and lots of snow, Chicago winters are ideal. Brian from Brian's Coffee Spot can tell you all about that!

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