While the likes of New York might get the most attention on the US's East Coast, Chicago feels like its slightly more understated yet gloriously cultured cousin. The Midwest’s coolest metropolis is the ultimate place to go for cool girls and culture nerds, stuffed full of blues bars and deep dish pizzas - and a skyline that’s worthy of a hundred photographs.
First up, where to eat:
Marisol Restaurant at Museum of Contemporary Art
It's hardly surprising that eating at the Museum of Contemporary Art feels like eating in an art gallery - it's because you are. The space is white, airy, walls filled with beautiful artwork. The food is tasty and modern. We had sunflower hummus, a crispy lion’s mane mushroom sandwich, and a melon and prosciutto salad sprinkled with candied walnuts, finished with a sorbet in peach-lemonade-green-tea form. Afterwards, I checked out the Yoko Ono exhibit.
Located at Marina Towers, the supper club is dark and moody. The restaurant is candle lit and instantly mysterious. A live jazz band plays in the background, while you dine. The restaurant serves up traditional American offerings, such as steak and lobster ragout. It's an upscale spot, with a grand piano & fireplace. The service is impeccable. For me, dinner began with a chocolate martini. I cannot recommend the garlic bread enough: stuffed with mascarpone and garlic butter. Decadent and utterly delicious, easily my favourite meal of the trip.
This no frills spot was used in The Bear. It's a run down yet rustic take out shop. Think 'shabby chic' vibe. Their speciality is one thing: slow cooked thin sliced beef, in Italian soft white bread, hot celery relish and sweet marinaded bell peppers. It’s less of a sandwich and more a messy, meaty memoir. It's a popular spot for locals and tourists, so get there early.
On the north side of Chicago, Margie's is an old fashioned all American diner, trapped in a time capsule. Wood paneled walls, old juke boxes, vinyl booths and vintage mirrors. The hot fudge sundae arrived with a gravy boat of melted chocolate served with a 1920's spoon.
Finish your Chicago crawl in this friendly German eatery. I was served a warm yet alarmingly huge, salty pretzel with honey mustard and beer cheese dip, washed down with grape cream soda. Because salt and sugar hydration is important. By this point, your bloodstream is 80% butter, but your soul is happy.
Does what it says on the tin! Delivers a 1950s inspired diner, with all the expected classics. Take out malt milkshakes, Italian hot beef sandwiches, classic hotdogs.
Where to stay
The Chicago Athletic Association
The Chicago Athletic Association is a former men’s club turned boutique hotel dripping in solid white marble, an original ornately tiled floor, mahogany, and millennium park views. Think Hogwarts meets Soho House, with a rooftop bar Cindy’s that'll make your Instagram fans weep with gratitude.
Straight from the 1800s, the boutique hotel greets you with a grand staircase, leading up to a games room, with impressive rooftop views. The lobby feels straight out of The Great Gatsby, while Cindy's serves a skyline view so stunning, you’ll momentarily forget how you got there.
The location sits straight across Millennium Park. Stumble out of bed and into a selfie at The Bean, all before breakfast. You can easily walk to the lake and Clarence F. Buckingham Memorial Fountain too.
What to do
The Chicago Architecture Center River Cruise Aboard First Lady is a cinematic way to see skylines, floating between glass giants and gothic towers whilst learning architectural secrets. Sip a coffee on deck, while the skyline poses for you.
The American Writers Museum added a touch of literary flair with interactive exhibits, celebrating Hemingway to Maya Angelou. I thought myself quite hilarious when I sat at an old fashioned type writer and wrote a poem about how jetlagged I was.
We strolled through a Greeter Tour of Lincoln Park. A beautifully laidback yet up-market neighborhood, filled with historical charm, indie shops that make you want to move immediately. As a Brit, I loved seeing how much effort went into Halloween decor.
Things got familiar with the Downtown TV & Movie Sites Tour, turning Chicago into one giant film set. Shout out to Ferris Bueller’s Day Off, The Dark Knight, and The Bear.
Speaking of which, Yes Chef: The Bear-Inspired Food Tour hopped us between spots featured in or inspired by the show. It felt like stepping straight into the chaotic culinary universe, minus the stress.
I learned loads of cool historical facts. My favourite being; the Italian beef sandwich was born during the Great Depression, a time when money was tight, families were huge, and cows were nervous. Italian immigrants figured out if you shaved beef thin enough to read a newspaper through it, you could feed big families and have leftovers. At the time, the U.S. Food and Drug Administration began tightening regulations, which meant meat companies ended up with cuts the FDA considered undesirable. Workers were often allowed to take scraps home.
The Chicago Magic Lounge delivered a perfect night of cocktails, illusions, and speakeasy glam. We entered through a secret backdoor entrance, escorting via a portal at the back of a launderette shop. The magic began right then.
Rosa's Lounge is a full-blown family affair born from an Italian man’s very specific dream. Owner Tony Mangiullo decided Chicago was cooler than pasta, and moved from Italy to chase the blues. He opened in 1984, naming it after his mum, who followed him across the ocean to help run the joint. (Because that’s what Italian mums do.)
With a CityPASS, there was plenty of time to explore the Art Institute of Chicago at my own pace. CityPass is an all-access pass to the best city excursions. All tourist attractions are included in one easy to use app.
And finally, I loved hitting the Lakefront Trail, an 18.5 mile stretch of walkable shoreline path. Perfect for cycling, running, strolling. See impeccable city skyline views from North Avenue beach.
