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   ![The Best US City For A Boys Trip](https://media.slman.com/_NnfPziP3EpgKSCzGKSKHCSWjIQ=/800x0/smart/https%3A%2F%2Fsw18.sheerluxe.com%2Fsites%2Fslman%2Ffiles%2Farticles%2F2025%2F05%2Fsl-man-070525-site-assets-chicago-boys-trip-hero-thumb.jpg?itok=ajlmcOoM)

  

 

 



 

  Image: The Hoxton, Chicago 

 

 

 

 [Travel](/culture/travel) 

 



 /  07 May 2025  

#  The Best US City For A Boys Trip  


 Closer than LA, cheaper than New York. Chicago deserves more attention than it gets. Featuring sporting greatness, cinematic history, world-beating architecture, outstanding art and some signature fast food, this is our guide to why the Second City hits the heights for a city break with the boys…  
 

 



ByTobias Gourlay

 

 

  Image: The Hoxton, Chicago 

 

 

 



 

 

 

 

 ![](https://media.slman.com/i2qZkiIXO0TCIl3VenxmWAMNmqk=/800x0/smart/https%3A%2F%2Fsw18.sheerluxe.com%2Fsites%2Fslman%2Ffiles%2Farticles%2F2025%2F05%2Fslman-chicago-guide-portrait-1.png?itok=T0PD0hld)

 

 

@STEELEHEATHERRR

 

 

 

 

 

## WHY YOU SHOULD GO 

  

 

Al Capone and Prohibition. Ernest Hemingway and sobriety. Michael Jordan and gravity. Ferris Bueller and authority. Chicago’s greatest characters all exist in defiance of something. It’d be easy to think of the city the same way – a place whose greatness is fuelled by the ‘Second City’ jibes of New Yorkers. Maybe there’s been a little bit of that down the years, but Chicago today stands tall as a destination in its own right.

Shimmering on the shore of Lake Michigan, it’s a handsome midwestern charmer that is really now America’s third city, behind LA as well as NYC. Its smaller size – and better public transport – make it easier to get around on a flying visit. Logistical convenience on its own isn’t a compelling reason to go anywhere, of course, but our new favourite US city also has some much stronger cards to play.

Chicago is a serious sports town, where the best and worst moments of local teams echo down decades. A quarter of a century after basketball’s greatest player left town, the Bulls still play in the ‘House that Jordan Built’. Baseball’s Cubs went more than a century without a title. When they finally overcame the ‘Curse of the Billy Goat’ and won a World Series in 2016, they won it at Wrigley Field – the ballpark they’d been playing in since 1916. It took the White Sox, their rivals from the city’s Southside, almost 90 years to break their own ‘Curse of the Black Sox’. The Bears are one of the NFL’s oldest American football franchises, and they produced one of its greatest teams in 1985. They haven’t won a Super Bowl since, so the bar-room conversations about the ’85 Bears are still loud today. The Blackhawks are one of the NHL’s ‘Original Six’ hockey teams, and their legends too are legion.

New York has the more famous skyline, but Chicago is the original home of the skyscraper. In 1871, the Great Chicago Fire cut a swath through the city. The folly of wooden buildings was laid bare and architects decided to build back better. New materials and, praise god, the invention of the elevator meant they could go higher than ever before.

You can still feel the ambition and the new freedom today. It’s in the Mart – the world’s biggest building until the Pentagon opened – and in the Chicago Temple Building, a firework in stone that shoots conventionally upwards for 30-odd floors then explodes into neo-gothic extravagance at 130m up in the air.

Chicago’s best-known skyscraper is from a later era. The Sears Tower was the tallest building in the world until the late 90s. Now called the Willis Tower, it still has America’s highest roof deck, from where you can see four US states on a clear day – even though, to the east, there’s nothing but the shifting waters of Lake Michigan.

The parks and boulevards that define many of the neighbourhoods below have been described as an emerald necklace. A thousand feet up in the air, you can see the necklace, but it’s back at ground level where you’ll discover the food, the culture and the sport that will make for a gem of a city break.

 

 [ ![Chicago Athletic Association Hotel](https://media.slman.com/RUNmwtCW1zLAfUM_ZdwbR8M1PSg=/800x0/smart/https%3A%2F%2Fsw18.sheerluxe.com%2Fsites%2Fslman%2Ffiles%2Farticles%2F2025%2F05%2F2-slman-chicago-guide-chicago-athletic-club-hotel.png?itok=B_gMh1Oa)

 

 ](https://www.hyatt.com/unbound-collection/en-US/chiub-chicago-athletic-association-hotel) 

Chicago Athletic Association Hotel  


 

 

 

 

 

 

## WHAT TO DO 

  

 

We found three standout ways to see the city. First, climb one of its tallest buildings – as well as the Willis Tower’s [Skydeck](https://theskydeck.com/) with its glass-bottomed Ledge, the John Hancock Center has [TILT](https://360chicago.com/tilt), which leans you 30º out over the edge of its 94th floor.

Then take a [CAC River Cruise](https://www.architecture.org/city-tours/river-cruise). In their shadows at water level is where you can find out most about the skyscrapers all around you. Our expert guide used the buildings on the river to tell a captivating story of how the city got from early Beaux Arts relics and Art Deco beauties to the post-modern statements being made in glass today.

Now jump on one of the old Brown Line ‘L’ trains that still clatter around the Loop, snaking around the feet of the downtown skyscrapers. The elevated railway didn’t just give the Loop district its name. It gives Chicago its sense of place – which is why you see it in so many of the classic films set here, from *Planes, Trains &amp; Automobiles* to *The Fugitive* and *Ferris Bueller’s Day Off*.

One of Bueller’s best moments is in the [Art Institute of Chicago](https://www.artic.edu/). It remains a world-class museum with iconic paintings like *Nighthawks* and *American Gothic*. Pushed for time? Follow Bueller’s route through it and you’ll also catch big hitters from Pollock, Chagall and more.

For serene contemplation of a different hue, the [Chicago Bath House](https://www.bathhousechicago.com/index.html) is where Capone used to get a sweat on. Fashioned out of an old factory, [Aire](https://beaire.com/en/aire-ancient-baths-chicago) is a contemporary alternative with appealingly industrial stylings. Right opposite the Bath House in Wicker Park, [Independence](https://independence-chicago.com/) is an on-point menswear store doing a nice line in American brands that can be hard to come by back home. It’s a good spot to get to know Randy’s Garments, John Gluckow, Wythe, Dehen 1920 and others in person – the boys inside are also generous with their bar recommendations and local tips. Nearby [Saint Alfred](https://www.saintalfred.com/) leans more into streetwear, as does [Notre](https://www.notre-shop.com/) over in the West Loop.

 

 

 

 [ ![Chicago Athletic Association Hotel; Au Cheval; Chicago Blackhawks; Chicago Cubs; Pequod's; Pizano's; Soho House](https://media.slman.com/Z7IGdPpI7lIyfNiXkfK0vSdNMv8=/1920x0/smart/filters:no_upscale()/https%3A%2F%2Fsw18.sheerluxe.com%2Fsites%2Fslman%2Ffiles%2Farticles%2F2025%2F05%2F070525-chicago-asset.png?itok=hksVh4ZY)

 

 ](https://pequodspizza.com/) 

Chicago Athletic Association Hotel; Au Cheval; Chicago Blackhawks; Chicago Cubs; Pequod's; Pizano's; Soho House  


 

@auchevaldiner; @SteeleHeatherrr

 

 

 

 

 

 

And then there’s the sport. The Bulls and the Blackhawks share the United Center, where Jordan won three of his six NBA rings. When the Bulls are playing, mascot Benny the Bull does tireless work hyping the crowd, with co-ordinated support from the jumbotron that hangs from the ceiling. The Bulls today are not quite what they were in Jordan’s day (no team is really), but the quintessentially American experience they lay on remains hard to beat. For more about the classic Bulls team, the [Sports Museum](https://www.chicagosportsmuseum.com/) – right next to the Willis Tower – is a fun place where you can compare your wingspan to Scottie Pippen’s, and finally put to bed any lingering doubts about whether you might have made it in the NBA.

With the Bulls’ hardwood court swapped out for an ice rink a couple of days later, the Blackhawks game we caught flowed smoothly. After a famously rousing version of the national anthem, the only punctuation came from the crash-bang sounds of the local boys and the Pittsburgh Penguins charging each other into the side boards, then the celebrations of a 3-1 home win.

Any cricket fan will appreciate the rhythm and beauty of a sunny afternoon at Wrigley Field. Each year, the return of baseball announces that summer will soon be here. The gentle, early-season buzz around the historic ground was about Cubs newcomer Kyle Tucker, but this was veteran Ian Happ’s day – an astonishing catch marking his thousandth game as a Cub. As the home fans celebrated a 7-1 win over the San Diego Padres, we were left to wonder why you can’t get beer and hot dogs delivered to your seat at the cricket. In the likely event of leaving the ballpark wanting more, surrounding Wrigleyville is well set up for baseball fans – among the sports bars and merch shops, [Big Star](https://www.bigstarchicago.com/location/wrigleyville/) is the place to make the switch from dogs to burritos. Wrigley Field is the first place we’d go back to on any return trip to Chicago, but if you have a weakness for an underdog, head to the city’s South Side and catch the White Sox at Rate Field.

For the first time in a while, American football’s Bears might be the team the city is most excited about. Caleb Williams is a talented young quarterback with a high ceiling – and this year the Bears have a new head coach who might just be the one to unlock Williams’ potential when the NFL season starts this autumn.

 

 

 

 

 [ ![Art Institute Of Chicago](https://media.slman.com/PRgog3Ayhi4yuNOBDRgwcvf3wlY=/1920x0/smart/filters:no_upscale()/https%3A%2F%2Fsw18.sheerluxe.com%2Fsites%2Fslman%2Ffiles%2Farticles%2F2025%2F05%2F2slman-chicago-guide-chicago-art-institute.png?itok=xwtkJV0T)

 

 ](https://www.artic.edu/) 

Art Institute Of Chicago  


 

 

 

 

 

 

## WHAT TO EAT &amp; DRINK 

  

 

Anthony Bourdain loved Chicago, its people and their food. He visited for all three of his main travel shows, and was even won round by deep-dish pizza, the local style that divides the city like the Cubs and the White Sox. After a trip to [Pequod’s](https://pequodspizza.com/) in Lincoln Park, we’re with Bourdain. Just keep your toppings classic – pepperoni, green olives, green peppers and onions worked beautifully for us. [Pizano’s](https://www.pizanoschicago.com/) is another deep-dish specialist with a few places around town.

In the last few years, *The Bear* has reminded the world how stressful the restaurant business can be – and how good an Italian beef sandwich can be. The show itself is filmed at Downtown’s Mr Beef. [Al’s Beef](https://www.alsbeef.com/) is a classic option, but our favourite was [Johnnie’s Beef](https://johnniesbeef.shop/) – a mid-century roadside pitstop in Elmwood Park. Order your sandwich wet (dunked in the juices of the meat) and with sweet peppers, then finish with an Italian lemonade of shaved ice. Walk it all off with a tour of nearby Oak Park, the neighbourhood where master architect Frank Lloyd Wright had a [home and studio](https://flwright.org/explore/frank-lloyd-wright-home-and-studio), and built Prairie-style houses for many of his neighbours.

Andersonville is a low-slung, independently minded neighbourhood to the north of Wrigley Field. Clark Street is worth a wander for its record stores, competitively priced made-in-the-USA denim specialist Dearborn and more. When you’re done, [Big Jones](https://bigjoneschicago.com/) does southern cooking of the sort you don’t get at home – the fried chicken’s good, so is the crispy catfish.

Chicago’s bar game is strong, maybe too strong. There would be more names on this list if we hadn’t lost an evening in the L &amp; L Tavern. It’s a proper, no-frills, cash-only, queue-for-the-jukebox dive in the perfect location for anyone making their way back from Wrigley Field to downtown. Before we could start on its beer, there was Irish coffee on the house. The bartender said we looked cold; we can’t deny the night warmed up from there.

For the real-deal Chicago bar experience, the other names we picked up from trusted locals and fully intended to vet for ourselves are [Rossi’s](https://rossischicago.com/), the [Old Town Ale House](https://www.theoldtownalehouse.com/) and [Richard’s Bar](https://richardsbarchicago.com/). If it’s music you’re after, there’s the [Green Mill](https://greenmilljazz.com/) for jazz and the [Hideout](https://hideoutchicago.com/) for everything else.

 

 [ ![Al's Beef; Johnny's Beef](https://media.slman.com/Ty9vXBJNauPOBI2qcfkFt33CoMk=/800x0/smart/https%3A%2F%2Fsw18.sheerluxe.com%2Fsites%2Fslman%2Ffiles%2Farticles%2F2025%2F05%2F3slman-chicago-guide-where-to-eat-als-johnnie-beef.png?itok=NquEPMqb)

 

 ](https://www.alsbeef.com/) 

Al's Beef; Johnny's Beef  


 

@AlsBeef; @SteeleHeatherrr

 

 

 

 

 

 [ ![Pizano's](https://media.slman.com/n1x019sXjSnhMEGr4Mr_g4k_cfw=/800x0/smart/https%3A%2F%2Fsw18.sheerluxe.com%2Fsites%2Fslman%2Ffiles%2Farticles%2F2025%2F05%2F2slman-chicago-guide-where-to-eat-peqods.png?itok=PqQ9lxG9)

 

 ](https://www.pizanoschicago.com/) 

Pizano's  


 

@STEELEHEATHERRR

 

 

 

 

 

 

## WHERE TO STAY 

  

 

For a greatest-hits city break, the Loop location of the [Chicago Athletic Association Hotel](https://www.hyatt.com/unbound-collection/en-US/chiub-chicago-athletic-association-hotel) is hard to beat. Anish Kapoor’s shiny, perception-warping Bean sculpture is across the road in Millennium Park, next to the Art Institute. Built in a Venetian Gothic style, the hotel itself was once a gentlemen’s sporting club. It’s moved with the times, but retained the superbly indulgent interiors the gents chose for themselves. With three working fireplaces, the lobby exudes a sort of homely decadence, and there’s a sprawling games room and bar just off it. Up top, [Cindy’s](http://www.cindysrooftop.com/) is the property’s sole new addition – its views make the update worth it. Bedrooms are spacious, comfortable and in a manly palette the boys of yesteryear would recognise and appreciate.

The city’s more familiar accommodation options include a [Soho House](https://www.sohohouse.com/houses/soho-house-chicago) and The Hoxton, a couple of blocks from each other in the Fulton Market District. Both are within striking distance of [Au Cheval](https://www.auchevaldiner.com/), the restaurant that might do the city’s finest cheeseburger. For international luxe, there’s the [Peninsula](https://www.peninsula.com/en/chicago), halfway up the Magnificent Mile that runs north from the Loop. Right on the Chicago River, the [Langham](https://www.langhamhotels.com/en/the-langham/chicago/) occupies a masterpiece building from the great modernist Mies van der Rohe.

 

 

 

 [ ![Chicago Athletic Association Hotel](https://media.slman.com/DNzxNLY0kfQ7SS79rBo9wl3SWEg=/1920x0/smart/filters:no_upscale()/https%3A%2F%2Fsw18.sheerluxe.com%2Fsites%2Fslman%2Ffiles%2Farticles%2F2025%2F05%2Fchicago-athletic-club-hotel.jpg?itok=89fmsBbA)

 

 ](https://www.hyatt.com/unbound-collection/en-US/chiub-chicago-athletic-association-hotel) 

Chicago Athletic Association Hotel  


 

 

 

 

 

 

 [ ![Chicago Bulls](https://media.slman.com/X8w1HsMF9_MG_-y_OuuBbOt7zEU=/800x0/smart/https%3A%2F%2Fsw18.sheerluxe.com%2Fsites%2Fslman%2Ffiles%2Farticles%2F2025%2F05%2Fsl-man-chicago-guide-chicago-bulls-credit-steeleheatherrr.jpg?itok=YQHPDmqj)

 

 ](https://www.nba.com/bulls/tickets/single) 

Chicago Bulls  


 

@SteeleHeatherrr

 

 

 

 

 

## WHEN TO GO 

  

 

Chicago can have steel-hot summers and knifing winters. The transitions between them aren’t always straightforward either. This year’s St Patrick’s Day weekend in mid-March – when the Chicago River is dyed green and the city goes hard – was gloriously warm. Three weeks later, while we were there, snow was in the air again.

But we didn’t choose our dates for the weather. We chose them because it was one weekend when you could catch the Bulls on Friday night, the Cubs on Saturday, then back to the United Center for the Blackhawks on Sunday.

If it’s the [Bears](https://www.chicagobears.com/tickets/) you want to see, the NFL’s regular season runs from September to January. In contrast to the [Bulls](https://www.nba.com/bulls/tickets/single) (41), the [Blackhawks](https://www.nhl.com/blackhawks/tickets/single-game) (41), the [Cubs](https://www.mlb.com/cubs/tickets/single-game-tickets) and the [White Sox](https://www.mlb.com/cubs/tickets/single-game-tickets) (81 each), the Bears will have only eight home games this year, so plan accordingly. Struggling to get tickets for a particular game? StubHub is a useful resource if you can swallow the resale prices.

 

## HOW TO GET THERE 

  

 

[British Airways](https://www.britishairways.com/), [United Airlines](https://www.united.com/en/gb) and [American Airlines](https://www.aa.com/) fly direct from Heathrow to Chicago O’Hare, which is an 18-mile/$45 cab ride from the downtown Loop district. Blue Line subway trains also go there direct from the airport. Flight times are about 8½ hours, with returns from around £400 at the time of writing.

 

*For more information, try* [*ChooseChicago.com*](https://www.choosechicago.com/) *first.*

[*CityPass.com*](https://www.citypass.com/) *is the place to buy a City Pass that will give you cheaper, priority access to the Art Institute, Skydeck, Chicago 360 and more.*

 

 

 

 

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