The Chicago Travel Guide: What To Do, Eat & Where To Stay
From some of the world’s most magnificent modern architecture to world-renowned museums, a buzzing food scene (made all the more exciting by TV hit The Bear) to incredible live music every night, there’s no wonder we’ve fallen for Chicago’s charm. Read on for the ultimate Chicago travel guide…
America’s second city? No chance. Although Chicago got its nickname based on the fact it was more or less rebuilt from the ground up after the devastating Great Fire of 1871, it’s often overshadowed by the bright lights, Big Apple vibes of NYC or the laidback, açai bowl-infused wellness and celeb spots of LA. But it is anything but second place in my book. Rather, it brings its own charm, a melting pot of cultures, banging music scenes and strict but somewhat charming rules on how to eat a hot dog – more on that later.
And now, thanks to a unique US Customs and Immigration pre-clearance in Ireland, travelling from the UK has never been easier. Fly through Dublin and benefit from going through customs before you board, which definitely shaves off a good few hours on the other side of the Atlantic, giving you more time to soak up the city. Trust us, you’re going to need it.
Things To Do In Chicago
Take In The Arts
Whether you’re into the watercolours of Monet or Hemingway’s prose, there’s a museum for you in Chicago.
The Art Institute of Chicago was one of my first stops, and it blew me away with its depth and breadth of modern masterpieces. Room after room of iconic works and a roll call of just about every 20th-century artist – Renoir, Monet, Picasso, Hopper, you name it. You can spend hours in this place so carve out a decent chunk of the day; make a point to view one of the museum’s most famous works, American Gothic; be blown away by the Thorne Miniature Rooms – 68 rooms shrunken down to Borrower size works of art from English cathedrals to1960s LA homes; and don’t miss out on the very tasteful gift shop.
If literature is more your thing, the American Writers Museum, just up the road, is a celebration of America’s most famous wordsmiths. I weaved my way through the likes of Ernest Hemingway, Cormac McCarthy, Sylvia Plath, Joan Didion and many more, and definitely came away with an unrealistic new reading list. The museum is engaging for people of all ages with a dedicated children’s area and sweet interactive stations like typewriters to create the opening page to your debut novel.
On the same stretch of Downtown Chicago you’ll find Millennium Park and one of the city’s many public art spaces. Head here to see British artist, Anish Kapoor’s Cloud Gate (more commonly known as The Bean). Visitors can walk all around it, even under it and take in its liquid mercury-like surface, which makes for a great Instagram shot.
Take A Bike Tour Across The City
See the city on two wheels with Bobby’s Bike Tours. They have lots of different options depending on your time, stamina and how much of the city you want to see, or rather, eat in. I chose the Bikes, Bites and Brews tour, which takes you through some of Chicago’s landmarks, from the Pinterest-worthy mansions of Gold Coast to the home of The Cubs baseball team at Wrigley Field, and finally back along the Lake Front with an incredible view of the city skyline getting closer and closer. As the name suggests, you also stop off for some local bites and beers, from the iconic deep-dish pizza to the classic Chicago dog and one of the Netflix-famous Molly’s cupcakes.
Top tip: do this at the beginning of your trip, you’ll get a feel for the geography of the city and you can bookmark places you’d like to return to and explore more. It’s also a great way to tick off the places you want to see but don’t necessarily want to waste a big chunk the day on.
Jump Aboard A River Cruise
The Chicago River snakes through the city, passing through the famous Downtown area and finally into Lake Michigan, which is so expansive it feels like the sea. It’s a great way to take in the city’s architecture which Chicago is famed for, from the not-so-celebrated Trump Tower to the Wrigley Building, Jeanne Gang’s much-loved St. Regis to the ornate, champagne bottle-inspired façade of the Pendry Hotel.
Book in advance with one of Chicago’s First Lady tours and see the city from a completely different perspective.
Head To Pilsen
For an entirely different way to see the city amidst the famous river, museums and sky-scraping architecture, I’d really recommend a day trip to Pilsen. About half an hour from Downtown, this Mexican mini-town is a world away from the stars, stripes, and all-American feel of Chicago.
Here, you’ll find brilliant taquerias, Mexican bakeries with piñatas hanging from the ceiling, hipster tattoo studios, street art depicting the likes of Frida Kahlo and a brilliant National Museum of Mexican Art.
Here you’ll find brilliant taquerias, Mexican bakeries, hipster tattoo studios and street art depicting the likes of Frida Kahlo.
Top tip for seeing the city: Prebook Chicago CityPASS and download the app onto your phone. This will get you VIP admission and savings on some of the city’s biggest attractions, from The Art Institute to The Skydeck, where you can view the city over a glass floor 1,353 feet up – if you can stomach it.
Where To Eat (And What To Order)
The Two Rivals of Deep Dish Pizza
There are two main contestants in the battle for Chicago’s best deep dish: Lou Malnati’s and Giordano’s. I tried both, naturally, and the latter just pipped it to the post.
But, spoiler alert… From what I can gather, the locals rarely eat a deep dish – it sounds a bit like a Londoner visiting Buckingham Palace on a Saturday morning – but prefer the crispy thin based “taverna style” pizzas that the city has plenty off.
Nevertheless, it’s somewhat of a right of passage in the city and worth it for the Instagram shot of a two-foot-long cheese string as the slices are pulled away from the hot bubbling base.
The Chicago Dog
Something that locals regularly eat, and are fiercely proud of, are their Chicago dogs. Not to be confused with a regular hot dog, these have very strict rules on what goes on top. There are seven toppings in fact, from the neon green relish to the sports pepper, the dash of celery salt to yellow mustard and absolutely under no circumstances can you ask for ketchup. Trust us.
They are actually really delicious and a must if you’re in the city. I rate Superdawg Drive-In and Wrigleyville Dogs both for their retro charm, no-frills approach and all-American vibes.
Hidden Gems
For something a little cooler, head down to the Time Out Market where you’ll find a plethora of street food options from around the globe. The area itself is full of cool bars, trending restaurants and breweries, and it has a kind of Hackney Wick edge. I can recommend the smash burger from Big Kids, which I would happily go back for.
Chicago is renowned for its steakhouses, Italian-American cuisine and, more recently, fine dining options no doubt upped by one famous fiction chef by the name of Carmy, but, as with all cities, it pays to get a local recommendation.
I was lucky enough to be pointed in the direction of Avli On The Park, an excellent Greek-inspired option by Lakeshore East. The Spanakopita – feta-filled filo puffs of joy – and some of the best lamb chops I’ve ever had are my top two recommendations.
As well as Bar Goa, which is full of I-know-this-great-little-place’ charm. Inspired by a British gastropub but with South Indian food, dangerous cocktails and DJs every night, it’s a fun place to start your Friday or Saturday night in the city.
Order the Spanakopita – feta filled filo puffs of joy – and some of the best lamb chops I’ve ever tried at Avli.
Finally, I spent my last night away from the more touristy parts of the city and headed to Bronzeville, a predominantly African-American suburb. Here, I found Bronzeville Winery. The space bridges community, art, food and excellent wine. We dined over fresh octopus and female and Black-owned wines with the sounds of Chicago musician Sam Thousand and his sax in the background.
Catch Live Music Every Night
Chicago is synonymous with live music, from the Smashing Pumpkins to Jennifer Lawrence, Kanye to Earth, Wind & Fire. But it is the Blues that the city is best known for.
I headed to one of its most legendry Blues bars, Buddy Guy’s, for an evening of live music. The clientele is a bit like a traditional boozer in London – expect anyone – from bachelorette parties to tourists to regulars that come each week. Even if Blues isn’t your go-to, you can’t help but be impressed by these world-class musicians.
Where To Stay
I checked in to the CitizenM Chicago Downtown, which was ideal for such a jam-packed city trip. Created for the digital nomad, the hotel rooms are small but functional and the perfect place to rest after clocking up the steps, store your bags and get some emails done between exploring the city. The bar felt buzzy; there were great co-working spaces with little booths, coffee table set-ups and banqueting benches, walls and nooks filled with art, coffee table books or tongue-in-cheek neon signs. It’s not somewhere you would spend the day, but you don’t need to with so much on your doorstep.
My verdict:
At a music exhibition on the Navy Pier I spotted a plaque with the quote, “If New York is the Rolling Stones, Chicago is The Beatles.” This felt far more fitting than Chicago’s usual “Second City” moniker. Cool, ever-changing and less in your face than the aforementioned. There is no doubt I’ll be pulled back to Chicago’s charm sometime soon.
If New York is the Rolling Stones, Chicago is The Beatles.
How to get there from London
You can fly from the UK to Chicago via Dublin with Aer Lingus and benefit from US Customs and Immigration pre-clearance in Ireland, allowing them to arrive in the US as a domestic customer. The carrier offer up to 14 weekly flights to the ‘Windy City’.
Economy fares start from £229 return and Business Class from £1,179 return, including taxes and charges.
Visit aerlingus.com.
For more information about Chicago, visit choosechicago.com
