With its iconic architecture, wide-open streets, rowdy sports bars, delicious fast-food joints, and abundance of pretty parks, Chicago is an American city that’s easy to love. Those visiting the city of big shoulders in winter months can spend their time skating below the city’s lofty skyscrapers, dipping between cosy dives bars or shopping the Magnificent Mile. And if you’re in town when the city thaws out, you’re spoilt for choice for things to do. You could catch a gig in Millennium Park, take a boat ride along Chi-town’s backwards flowing river, kick back on the beach or cycle along the 606. But regardless of when you visit the Windy City, you’re guaranteed to be blown away.
Go to Bang Bang Pie & Biscuits (£) – a neighbourhood café-come-bakery draped in 1950/60s Mid-Western charm. For the sweet tooth, its famed sugary pies are a breakfast dream. Try a slice of chocolate pecan or zingy key lime pie for under a fiver. But don’t expect to saunter in as you would a Starbucks as queues are inevitable – especially on weekends. Don’t stress, though, they move quickly and it’s all part of the magic. Once you’re inside with fistful of roasted coffee blend and a baked treat, plonk yourself on a mismatched, colourful chair in the corner and get to work on your spoils. If it’s nice out, make use of the picnic benches in the grassy outdoor area.
Grab a moist, filling Italian beef sarnie. Before becoming a Chicagoan staple, this thinly sliced beef sub, which comes slathered in a rich meaty jus and sweet peppers, was a favourite amongst Italian immigrants. You can pick ‘em up all over town but we like Mr Beef, which has been around since 1963 or Al’s Beef (£).
Book a table at RPM Steak (£££) for melt-in-your-mouth beef at one of River North’s steak houses. This high-end restaurant, popular with celebrities and sports stars, serves up beef even the toothless will manage to devour. Steaks go from £35, so it’s not cheap, but you’d be hard-pressed to find a better cut of meat in the Chicago. If you’ve got plenty of cash to splash, treat yourself to Hokkaido snow beef (£126) – the rarest imported Wagyu beef available.
Chicago is known for its deep-dish pizza – a thick wedge of cheese and tomato dough that looks more like a pie – so it’d be rude not to give it a whirl. It’s contestable where does the best slab, but Lou Malnati’s, Giordano’s and Pequod’s (£-££) usually come out on top. Hotdogs are also infamous here, pick one up from local institution, Portillos.
Check out the city’s lankiest building the Willis Tower, which stands at 443 metres. To put things into perspective, the Eiffel Tower is 324 metres tall. If you’re feeling brave, walk the Skydeck (about £20) –a glass oblong jutting out from the building that attracts around 1.7 million people annually. It’s a touristy thing to do, so there’re often crowds, but it’s still well worth checking out. If you want something more casual, kick back at Cindy’s Rooftop for cocktails (about £12.50) overlooking the city.
You can’t go wrong with Millennium Park – Chicago’s answer to Central Park. The beauty of this sprawling green space, located in the heart of the city, is that it’s engulfed by colossal skyscrapers. Visit ‘The Bean’ (a massive, modernist, mirrored bean sculpture) or go ice-skating in winter months. If you’re in town in summer, why not catch a gig a free gig at the futuristic Jay Pritzker Pavillion?
Pop into the former-speakeasy-turned-neighbourhood tavern, Twin Anchors, to chew the fat with locals over a hearty meal. With maroon and cream checked floors, cute wooden dining booths and baseball playing on TVs, you’ll get a proper all-American dining experience. To blend in, order the famous BBQ ribs. Apparently, even Chicagoan actor Billy Murray is a fan.
You’re spoilt for choice. Chicago is a music city. And, like something you’d read on a bad Tinder profile, the city music taste is ‘eclectic’ – think blues, rock, classical, jazz. Visit Kingston Mines, perhaps Chicago’s best live blues hall, for foot-tapping, hip-shaking, all-round good vibes. The Green Mill is your spot for cocktails and jazz – lookout for the green neon sign. Meanwhile, soft-rock and indie fans should swing by the Empty Bottle – an underground, exposed-brick shadowy dive bar packed with bearded hipsters.
Immerse yourself in architecture. You might be aware that Chicago was home to the first-ever skyscraper, but did you know the Windy City is expected to become a megacity in 20 years? With that in mind, it’d be unwise not to have a wander around the Chicago Architecture Centre (about £9), which showcases the city’s future plans. Developed by a collective of architects, the blueprints aim to make Chicago more liveable, healthy and sustainable. If you’re you’re left with honey on your lips, why not jump onto the First Lady Architecture River Cruise (about £33) to see the buildings from a different perspective?
Head to Second City (tickets from about £7.50) for some stand-up comedy. This renowned Chicago comedy venue, co-founded by Bernie Sahlins, Howard Alk and Paul Sills, has been operating for 50 years. Over five decades, this lamp-lit, arched cinema-like venue has hosted many a famous face, from Dan Akroyd and Tina Fey to Bill Murray. Choose from a host of weekly shows and be prepared to giggle like you never have before.
Chicago is a brew city (Goose Island, Lagunitas and Revolution are all based here), so you’re never short of a frothy top. Although if you want to try an authentic local tipple, try Malort. Made from bitter-tasting wormwood, managing a shot of this pungent liqueur is a rite of passage. Two of its original marketing slogans are ‘kick your mouth in the balls’ and ‘tonight’s the night you fight your dad’, so you can imagine how it tastes…
Join the cool kids at Logan Square or Wicker Park. Here you can dip between dive bars, like Happy Village and the Rainbo Club, drinking cheap and making friends. Straight shooters might want to dress up fancy and head to the flashier bars in River North – London House’s has a spectacular rooftop cocktail lounge. Meanwhile, sports fans can watch a game in Wrigleyville, grab tacos at Big Star and head to Sluggers to wallop some balls in the batting cages.
You’ve got plenty of options. Chicago is a sport-mad city with at least 19 different teams. A Cubs game is a special experience. If you’re not in town in-season, book onto a tour of Wrigley Field (about £22), which took four and a half weeks to build back in 1914 and has hosted a ski jump competition, NFL games, ice-hockey matches, Elton John and Pele (not at the same time). Another option is to watch the Chicago Bulls shoot some hoops.
You’re not flush
Staying at The Freehand, an avant-garde hotel-come-hostel located in Downtown Chicago, is like staying over at a quirky independent cinema. Think mood lighting, brick walls and boho furniture. Private rooms are available, but if you’re on a budget book a dorm for around £16. Double rooms from £62, freehandhotels.com
You’re cushty
Zachary Hotel is a fancy, sweet-smelling, baseball-themed hotel that sits directly opposite the Wrigley Stadium in Wrigleyville. Named after the architect behind the Cubs’ stadium, it’s the perfect spot for sports fans. If you’re one of them, why not pay a few quid extra for a room looking out over the stadium? Double rooms from £154, hotelzachary.com
You’re a flash Harry
London House Hotel is a grandiose, 452-room hotel located on the intersection between North Michigan Avenue and Wacker Drive in the city’s business district. The four-star hotel offers some of the best views over Chicago’s dazzling skyline. Double rooms from £150, londonhousechicago.com
How do I get there? BA fly direct from about £268 return
Should I get a cab from the airport? Avoid traffic by taking the Blue Line for about about £4
How much is a beer? From around about £3-4
For more information about Choose Chicago visit www.choosechicago.com
