The Chicago Bucket List: 39 things to see, do and eat in the Windy City!
American city breaks
The Windy City boasts some of the most vibrant neighbourhoods in the US. Thomas Breathnach has your cut-out-and-keep guide...
Lights, camera, Chicago! Chicago’s iconic Loop (above) serves as “Downtown” to every native from Lincoln Park to Wisconsin. With world-class dining, epic architecture and buzzing theatre, The Loop is perhaps the only urban hub in the US. to match the bite of the Big Apple but, wandering around, you’ll soon discover its uniquely Chicagoan feel: locals smile more, taxis honk less and there’s almost a mega-village air to the city known as the Pulse of America.
Eat & Drink:
Chicagoans adore their breakfast so join the lines at one of the Loop’s most popular morning spots, Wildberry (wildberrycafe.com; mains from $12/€10). Order their walnut pancakes, a sizzling skillet, or both.
Come lunchtime, the Revival Food Hall (revivalfoodhall.com; $12/10), is a quirky caucus of the city’s top artisan vendors. Hit Farmer’s Fridge for imaginative mason jar salads, the Fat Shallot for a dreamy grilled cheese, and Black Dog Gelato for (why not?) goat cheese cashew caramel deliciousness.
For dinner, Chicago has an all-star cast of restaurants wooing the theatre masses; old school Berghoff (the berghoff.com; $18/$16), with its outstanding steins and schnitzels, definitely needs a ressie.
Chicago boasts a blockbuster skyline, but Willis Tower (formerly known as the Sears Tower, F.Y.I.) with its glass floor Skydeck (theskydeck.com; $23/€19) is the most visited of them all. The views are unmatched, though queuing Instagrammers may see your stress levels spiral beyond its 110 floors — consider joining the Skydeck’s yoga and mimosa groups ($45/€38) in November.
Don’t think of Chicago as just a city. It’s a river, too. The Chicago River follows an magnificent urban course before flowing into Lake Michigan. Meander along the chilled-out Riverwalk, grab a yellow water taxi downriver or, for a real city escape, kayak along its banks (urbankayaks.com; $45/€38).
Got jazz hands? The Loop is Chicago’s theatre central with current runs including the Elvis-inspired Million Dollar Quarter and the acclaimed Hamilton. You don’t have to pay Broadway prices either - check out hottix.org for last minute ticket deals.
All CTI tracks lead to the Loop. From O’Hare, grab the blue line to Clark/Lake.
Cheap city tour? The L train’s Blue, Pink and Brown lines snake largely overground, offering amazing views of the Loop. Board a front carriage for the best angles (transitchicago.com; $2.25).
Bienvenidos a Pilsen! Once the hotbed of the city’s Irish, German and Czech communities, today artsy Pilsen (pictured right) is home to the Midwest’s most vibrant Mexican community and the hottest influx of hip Chicagoan creatives. Spend a morning here and you’ll wander between gritty blocks of delis, lavenderias and bodegas, as well as blocks of up-cycled warehouses home to Chicago’s labradoodle and latte set.
Its dynamic evolution is not without its turbulence, however. Pilsen’s rising rents are seeing the immigrant community, whose culture inspired the foodie it-spots, being squeezed out of the ’hood: a story fervently depicted in the city’s vibrant mural scene. But this makes Pilsen all the more intriguing: raw and real, the neighbourhood is an American case study in gentrification.
Eat & Drink:
With its Latino roots, Pilsen is where Chicago meets Chicano. Mezcal and tequila bars are the new craft whiskey haunts, guac and margarita menus are the new wine and cheese. And forget taquerias: birrierias, restaurants specialising in Mexican goat stew, are the new craze. ¡Que delicioso!
For breakfast, head to Crepería Nuevo Leon (creperianuevoleon.com; ($9/€8) for pancakes from the savour (with pepper and chipotle sauce) to the oh-so sweet (with Mexican cajeta caramel). Lunchtime highlights include Carnitas Uruapan (carnitasuruapanchi.com; $5/€4) which traditionally slows-braises juicy pork, best enjoyed with tacos and salsa verde. Come la noce, inventive cocktail bowls at the Punch House basement bar (punchhousechicago.com) are worth opening a tab for.
Pilsen’s landmark building is an attraction in itself. The exquisite Thalia Hall could be on a street corner of Vienna or Prague — Bohemian-inspired, today the venue has more of a boho edge, attracting acts from indie newcomers to Smashing Pumpkins.
Art lovers should make a beeline to the National Museum of Mexican Art (nationalmuseumofmexicanart.org; free), the largest institution celebrating Latino culture in the U.S., its 10,000 exhibits range from folk art to photography, with the museum’s sin fronteras (without borders) mission a poignant hot patata right now.
Take the CTA pink line to 18th Street or orange to Halsted.
Tag your visit to the second Friday of every month. That’s when Chicago opens its doors to some of city’s best galleries, like Pilsen’s Arpentry, for free (chicagoartsdistrict.org).
If Wicker Park is home to the avocado toast addict, Logan Square is all about the community gardening artist who grows her own Swiss chard. The neighbourhood sits just three subway stops north of Wicker Park (or in gentrification terms, about five years). Venture beyond the main-drag and you’ll find some of Chicago’s most attractive neighbourhoods, where elegant greystone townhouses nod to the district’s affluent roots. Add in some greenspace and you can see why Logan Square makes such a handsome ’hood.
Eat & Drink:
Want the 411 on the next foodie niche to hit Chicago? Gourmet breakfast, no less. Newly opened Jam (jamrestaurant.com) proves that what Logan Square residents save in rent, they pay back in brunch. Try the malted custard French toast, a dream hunger-stop from $13/€11.
For lunch, visit lower-key but vibey Johnny’s Grill, a heaving diner where local grandmas chow into beef chilli alongside gamers coming out for air (thejohnnysgrill; $10/€8).
Logan Square’s coolest joint is Parson’s (parsonschickenandfish.com; mains from $16/€14), a retro-revival 1950s luncheonette, where locals drink, dine and play ping pong to the vibe of a block party. Enjoy buckets of fried Amish chicken and slushy negroni cocktails outdoors in their trippy candy cane umbrella patio.
Logan Square is a non-stop, stumble-upon of quirky record stores, bookshops and, yep, video game bars. Logan Arcade (loganarcade.com) on Fullerton Avenue taps into nostalgic computer kitsch and craft-beer crazes, with IPAs and Pacman a winning combo.
Need a slice of rustic in the city? While American farmers’ markets tend to push the definition of ‘local’ a smidge, Logan Square’s friendly gathering goes the distance in staying regional (logansquarefarmersmarket.org). Amid juices and tasty bakes, Logan Square Farmers’ Market also hosts a neat travelling vintage store called Bus Shop.
Grab the blue line to Logan Square.
Fancy telling a bunch of strangers about your life story? The Logan Theatre offers open mic comedy every Monday (thelogantheatre.com).
The Magnificent Mile
With 460 stores, 250 restaurants and 22 million shopaholics visiting annually, Chicago’s Mag Mile is America’s ultimate open-air mall. Rivalling New York’s Fifth Ave and L.A.’s Rodeo Drive as the country’s real estate queen, you can expect every global label from J. Crew to Jil Sander here. But it’s not all about the Macy’s points. Get out of the fitting rooms and you’ll find a cauldron of culture, celeb chef restaurants and world-class museums.
Eat & Drink:
Home to Chicago’s top dining scene, The Mag Mile caters to every imaginable palate — from gourmet ramen to organic ceviche. Being Chicago, pizza is a good place to set your culinary compass and legendary Lou Malnati’s (loumalnatis.com; $10/€8) makes a fine intro to deep dish.
For finer dining, Bandera is a Southwest-inspired American favourite with a menu featuring cajun trout and a soundtrack of live jazz (banderarestaurants.com; $19/€16).
For post-shopping cocktails, Three Dots and a Dash is a Polynesian-style tiki bar offering tropical mixes with serious kick (threedotschicago.com; $9/€7).
Credit cards, flat pumps and empty case at the ready?
The Mag Mile will excite the most jaded of jet-set shoppers. And you don’t need to max out. Along with “where’s the price-tag” designer stores such as Vera Wang and Marc Jacob, you’ll also find fast-fashion US labels including Forever 21 and American Girl. See also themagmile.com.
Beyond Gucci and Co., you’ll also discover some of Chicago’s best cultural attractions. The Chicago History Museum (chicagohistory.org; $16/€13) and Art Institute of Chicago (theartic.edu; $25/€21) make for two stellar outings in their own right, while the Chicago Sports Museum (harrycarrays.com; $10/€8.50) and Chicago Children’s Museum (chicagochildrensmuseum.org; $14/€12) are a big hit with families.
Take the Red line to Chicago or Grand Ave.
If you’re an attraction junkie, consider buying the Chicago CityPASS (citypass.com/chicago) for $99.75/€90. It includes admission to five of the city’s top attractions and also allows you to leapfrog the queues.
Wicker Park & Bucktown
Northside neighbours Wicker Park and Bucktown have brewed into such urban wunderkinds, they’re frequently hailed as America’s trendiest hoods. Formerly known as the Polish Gold Coast, today the quirky quarters are perhaps more kale than Kielbasa… but that’s the beauty of Chicago. The Windy City is ever in flux.
Stepping out from the Damen train stop, there’s the instant buzz you’d experience in the likes of Brooklyn’s Bedford Ave or Toronto’s Queen West. But while Williamsburg seems to have become a parody of itself, Wicker Park and Bucktown have kept their laid-back Midwest loafers firmly on the ground. Come for lazy coffee mornings; stay for the cocktail bars that keep Milwaukee Ave pumping all night.
Eat & Drink:
Start with your daily grind at Ipsento (ipsento.com). One of Bucktown’s top coffee shops, this season’s must-carry caffeine accessory is their trending pumpkin spice latte.
Come noon, pull up a stool at Dove’s Luncheonette (doveschicago.com; $15/€13), a new diner where Chicago blues, borderlands’ fare and cheeky beermosas (breakfast cocktails) do the talking. Going late night? The Hideout (hideoutchicago.com) is one of the neighbourhood’s best dive bars… here, even conversations over Wilco’s best album get heated.
While the Mag Mile boasts every high-street label going, the boutiques and pop-up designers of Wicker Park are more about grassroots haute couture.
To get a flavour of local trends, visit the likes of Anastasia Chatzka (anastasiachatzka.com) on Damen Ave. Looking for something completely different?
The latest hipster sport of Whirlyball (a has-to-be-seen hybrid of bumper cars and lacrosse) needs all 50,000 square feet of a Bucktown game hall to contain the raucousness (facebook.com/whirlyball).
Take the Green or Blue line to Damen.
Knock on the concealed doorway at 1520 North Damen. You’ll discover one of Wicker Park’s hottest speakeasy cocktail bars (theviolethour.com).
The Christmas Quarter
Feeling festive? Chicago hosts the largest annual Christmas market west of the River Rhine. From Nov. 17 to Dec 24, downtown Daley Square is transformed into a Bavarian wunderland with 200 stalls celebrating the Midwest’s German roots. Expect glühwein, bier and bratwurst in super-sized supply (christkindlmarkt.com).
Downtown, but not quite downtown, Fulton Market in the West Loop is one of the most accessible alternative neighbourhoods for those based in the CBD. From the Loop, a 20-minute wander west takes you past the lively tavernas and cafes of Greektown towards the edgy streets of Fulton Market. Here, at the former site of Chicago’s meat-packing district, tourists will find a true foodie wonderland, with a mouthwatering bevy of restaurants, bars and clubs scattered among one of the most vibrant art scenes in the city.
Eat & Drink:
Fulton Market Kitchen (fultonmarketkitchen.com; $24/€20) is part-gallery, part-cocktail bar and part-restaurant. Expect a drinks menu and art collection curated as cleverly as each other, with small batch spirits and craft cocktails enjoyed amid a backdrop of the city’s most en trende artists.
While artisan gin bars come and go, Chicagoans will always love their wine. The district’s City Winery (citywinerychicago.com; $15/€13) offers 20 in-house and 400 imported vintages. Its Mediterranean restaurant also offers artisan cheeses, charcuterie and meatball plates to pair with your picks.
Come evening, stylish Beatrix nails every bistro classic from steak frites chimmichurri to its tall, dark & handsome gluten-free chocolate cake (beatrixrestaurants.com; $26/€21).
Art and design lovers will luck out in Fulton Market. Amid the criss-cross of restored warehouse spaces, pay a visit to Mars Gallery (marsgallery.com; free), a legendary local showcase for pop artist Peter Mars. Mixing work and pleasure? Fulton Market is also home to a vibrant co-working scene with spots like The Study (thestudychicago.org) offering daily drop-in rates for just ten bucks. Their motto promises results, too: “Your productivity is here because your pets are not.”
Take the Pink or Green line to Morgan.
Travelling on a budget? Check out chicagoonthecheap.com for the best deals on events, dining and attractions in the city.
For more info, see choosechicago.com
Did you know
New York has its High Line, but Chicago has an elevated park too. Opened in 2015, The 606 peddles past 2.7 leafy miles of the Northside's top neighbourhoods, from Humboldt Park to Bucktown. Have a walk, or saddle up with Chicago's shared bike scheme (divvybikes.com; $10/€9)
Meet 'n' Greet
Looking for a local hero? Then book your personal Chicago Greeter! The voluntary body of 200 eclectic locals offer individual, or small group, travellers insider guides of the Windy City. Tours are free (tips are discouraged) and when registering online you can filter your own precinct preferences to everything from LGBT Chicago to art and architecture (chicagogreeter.com)
Where to stay
A downtown base is best for neighbourhood-hopping. I checked into Hotel Allegro (allegrochicago.com; $76/€65pp), a boutique Kimpton haven amid the Loop’s buzzing theatres.
Magically restored to its Roaring Twenties roots, the hotel is as seductive as a freshly served sidecar with moody boudoir suites and a sexy art deco lobby. Fancy more? A complimentary Happy Hour features all-you-can-quaff Prosecco, darlings.
In the hood:
If venturing beyond Chicago’s downtown, most hotel options involve cookie-cutter chain hotels or budget inns. There are fantastic trending exceptions emerging, however.
The Robey Hotel in Wicker Park is a former Mad Men style office block turned slickly refurbed bolthole, for one. Rooms from $195/€165 should appeal to hipster hotel junkies and the alternative business traveller (therobey.com).
Watching the dollar exchange? Airbnb (airbnb.ie) has a Craig’s List worth of great value properties from converted lofts in Fulton Market to roomshares with local creatives in Bucktown. There are savings, too: you’ll find Chicago Airbnb prices about 10pc cheaper than in NYC.
Given the current transatlantic fare wars, there’s never been a cheaper time to visit Chicago.
Aer Lingus (aerlingus.com) has Saver Fares from Dublin to O’Hare from €199 each way (Smart Fares, which include check-in luggage, start from €259).
Meanwhile, WOW air (wowair.ie) offer flights from Dublin to O’Hare (via Reykjavík) from €130 each way (baggage is extra), and American (aa.com) runs a seasonal route from Dublin during summer months.
Read more:The New York Bucket List: 25 things to do in the Big Apple before you die!