From places to stay to the perfect theatre night to go on a date, here is all you need to know.
Scoff miso brownies
Fuel up for the day in leafy Logan Square, Chicago’s hipster hood.
At Lula Cafe the daily changing menu features whatever’s freshest at the farmers’ market.
Our sour-sweet beets on bruschetta with smoked pecans and whipped goat’s cheese, £9, was seriously good (Lulacafe.com).
Next door, Billy Sunday bar specialises in vintage Italian digestifs (Billy-sunday.com).
Sink a cheeky glass before hitting up award-winning The Bakery at Fat Rice, where sweet treats are given Asian-style twists, like gooey fudge brownies with salty miso, £3 (Eatfatrice.com).
Have a giggle
Check out the world’s tiniest rooms at The Art Institute of Chicago, entry £22 (Artic.edu).
The Thorne Miniature Rooms recreate 68 historic settings in incredible detail at a scale of 1in to 1ft.
Then dig into deep-pan pizza at nearby Giordano’s, from £12.50.
It’s less pizza, more gigantic cheese and tomato pie (Giordanos.com).
End the night at Second City theatre. Known for launching Hollywood heroes Tina Fey, Steve Carell and Bill Murray, it hosts nightly improvised comedy shows.
Tickets cost from £23 (Secondcity.com).
Chicago is known for its extravagant skyscrapers.
Hop on a river cruise with the Chicago Architecture Foundation and gape at sights like Aqua Tower, with its wavy, coral-like balconies.
A 90-minute tour costs £34 (Cruisechicago.com).
Afterwards, the terrace at Cindy’s gives knockout views of downtown and twinkling Lake Michigan.
Drink it in with a punchy Siempre Si cocktail of pineapple, tequila and chilli, £12 (Cindysrooftop.com).
Opposite in Millennium Park, snap a selfie in art installation Cloud Gate, known as The Bean because of its shape.
Loop The Loop
Glide around lakeside Grant Park on a Segway tour in central district The Loop, £50 for two hours (Chicagosegways.com), before hopping off at Kim and Carlo’s hot-dog cart.
Ask them to “drag it through the garden” for all seven toppings: mustard, onions, pickle relish, tomato, dill pickle, celery salt and spicy pepper, £3.45.
The Loop’s biggest landmark is the 1,450ft Willis Tower.
Visit the 103rd floor Skydeck, entry £18, and try stepping inside the glass boxes extending out from the building (Theskydeck.com). Eek!
Catch The Bulls
Koval Distillery makes lush tipples like peach brandy and cranberry gin.
Get a taste with a one-hour tour, £8 (Koval-distillery.com).
Later, you really can’t beat the atmosphere at a Chicago Bulls game.
Catch the basketball team at the West Side’s United Center, from £20, and pose for a pic with the Michael Jordan statue.
Drink at a barber’s
At The Aviary, watch “drink chefs” fuss over bubbling potions that are part cocktail, part performance art.
To swig the (719)26-OATES, £18, you have to stick your head inside
a plastic bag (don’t try this at home, kids)!
Find it in the trendy West Loop and reserve ahead (Theaviary.com).
More low-key? Over the road, Blind Barber is barbershop by day, speakeasy by night (Blindbarber.com).
When you’re ready for bed, a block away is Ace Hotel.
Housed in a former cheese factory, it has industrial-cool rooms and a rooftop bar. Double rooms start from £130 a night (Acehotel.com).
The Chicago River is the only waterway in the US that flows backwards.
Engineers reversed it in 1900 to divert sewage away from Lake Michigan.
Plan your trip at Choosechicago.com.
Return flights from the UK start from £259 (Norwegian.com).
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