Deck the Malls: Christmas shopping tips for New York, Boston and Chicago

Thomas Breathnach breaks out his big city Christmas shopping tips for travellers heading to New York, Boston and Chicago this season.

by Thomas Breathnach

1. New York

Over 100,000 Irish travellers fly Stateside for the annual transatlantic shopping splurge and, unsurprisingly, most of them fill their Christmas stockings in NYC.

The Big Apple might still be struggling to find itself a post-Carrie Bradshaw style icon, but in terms of trends, bling is out – and with the city’s Garment District booming again, local designers are most certainly in. This season’s must-wears? An NYC tailored dip-dye gown simply accessorized with a Black Friday iPod shuffle.


It’s mad and it’s manic, but Midtown Manhattan still remains the retail powerhouse of the world. Given the demand, many of the city’s Black Friday deals now start on Thanksgiving Thursday (November 27), so you don’t have to worry about pitching a tent on Fifth Avenue to queue early morning.

Macy’s on 34th opens at 6pm, Toys “R” Us on Times Square opens at 5pm while Bloomingdales is holding off until 7am. Be sure to grab stores’ “doorbuster maps” as soon as you enter so you can dash through the deals quickly.


For a less chaotic follow-up, take lunch at one of the charming pizzerias of Nolita and wander off-the-grid to Soho. As Manhattan’s prime fashionista territory, here you can peruse the vitrines of American designers like Marc Jacobs, Jill Stuart and Anna Sui. Other hot name boutiques to keep an eye out for include Curve on Bond St and vintage store Armacord on Lafayette.


Brooklyn’s Williamsburg may be losing its edge to nearby Bushwick, but its streets are still stacked with garment gold. On Bedford Ave, you’ll find beatnik boutiques, thrift shops and Polish grannies selling winter furs on street stalls. Monk Vintage is a local haunt for bargains: try trading a few things from home to barter off a few bucks. For a higher-end shopping experience, pop-up fitting stores by local tailors are an emerging trend. Brooklyn-based designer Alisha Trimble can design and fit a client’s outfit during their stay and ship their tailored gúnas back to Ireland.


When it comes to shopping sprees, The W Hotel Union Square bags the best “location, location” gong. Its stylish, contemporary suites are primed between Park Ave and Downtown, making it superbly positioned for midday baggage drops. The hotel also sits right on the doorstep of the Union Square Christmas market as well as the L line, making it just a six-minute subway ride to Williamsburg. Rooms from $340;

2. Boston

Boston may bag the raspberry as America’s worst-dressed city but there’s still a lot more to Massachusetts’s capital than Ralph Lauren polo shirts and the Harvard hoodie brigade.

The city’s simple-to-ramble centre makes it easy to flit between real fashion finds, from artisan design houses to stylish New England outdoor stockists. Thinking of making a healthy start to 2015? This sports-obsessed town is one of the best spots on the East Coast to snap up top quality fitness gear.


Downtown Crossing is one of Boston’s main business and tourist drags – Macy’s attendants are so familiar with Irish customers here they can roll off the 32 counties. Copley Place and ‘The Pru’ (Prudential Center) make for pleasant mall meandering but for a lot more flair, head to Newbury St, Boston’s stylish brownstone avenue which bustles with brunch-munchers and bargain-hunters.

Our tip? Stock up on winter cabin chic at The Tannery.


In a city that brings you the Patriots, the Red Sox and one of the world’s most famous street races, it’s little surprise Boston retail is geared up for sport. The Marathon Sports is a city institution and a great spot to basket some quality trainers, while the basement section of trendy City Sports is known for its excellent clearance sales. Lululemon on Newbury is also a great spot for high-end yoga gear, so you can be at your most stylish while maintaining that downward dog.


With the advent of online shopping, the allure of outlet stores seem to have dipped but Wrentham Village, just outside Boston, still merits a visit. High-end stores like Barney’s and Saks stand beside staple favourites like Calvin Klein and The Gap. If you’re not driving, Boston Common Coaches operate hotel pick-up and drop-off services for $40 and also offer a Midnight Madness excursion which leaves the city on Thanksgiving night.


Everyone gets an upgrade at the Eliot Hotel, a colonial boutique bolthole located in the city’s trendy Back Bay. All rooms here are in fact sizeable suites, so you won’t have to trip over your Nordstrom bags when you hit the feather at night. Downstairs the hotel also houses Boston’s top sushi restaurant as well as the ambient Clio bar for a late-night cocktail. Rooms from $205;


“Check out the SOWA Market for its great combination of artisan made-pieces, timeless vintage clothing and accessories” says Krista Casey, blogger.

3. Chicago

It's the Great Lakes' great escape. Every Thanksgiving, millions of folks from Midwest suburbia make the SUV haul into Chicago for Holiday season bargains.
It’s the Great Lakes’ great escape. Every Thanksgiving, millions of folks from Midwest suburbia make the SUV haul into Chicago for Holiday season bargains.

What’s to see? One of the greatest shopping streets on Earth, one of America’s most happening neighborhoods and one of the world’s biggest Christmas markets. Plus, being the pearly white Midwest, Chicago is also home to perhaps the friendliest customer service you’re likely to encounter in the US.


Stocked with everything from Armani to Zara, the high-end strip of Michigan Avenue is Chicago’s very own Fifth Ave or Rodeo Drive. Also known as the Magnificent Mile, the USP here is the concentration of 460 stores, 275 restaurants and 50 hotels. But you need to go beyond it. The hipster neighbourhood of Wicker Park is stacked with alternative boutiques and cafes for a more artisan experience. Eskell on N. Milwaukee Avenue is a cutesie gem of a boutique featuring in-house made jewellery and edgy threads while the Silver Room supports local designers.


Black Friday bargains are perhaps even more synonymous with gadgets rather than garments as it’s one of the best days of the year to pick up knockdown electronics or a bargain iDevice. Even Apple Stores (both in Chicago and right across America) offer rare (but paltry) discounts on Black Friday. For the Windy City, resellers can be a better bet so check out the deals at the likes of tech giants Best Buy, located on 875 N Michigan Ave. Don’t forget a plug converter.


On the back of the Illinois’ huge German population, Chicago is in fact home to the biggest Christmas market west of the River Rhine. Come Yuletide, over 170 stalls make their fairy-lit presence across Daley Plaza, where Bavarian wurst merchants stand side by side with local hipsters necking back gluhwein. Throw in the cosy merriment of an Alpine apres-ski party, and you’ve got a fantastisch backdrop to wrap up a day’s shopping.


You wouldn’t suspect it, but Hotel Palomar in Chicago’s North River district is in fact a chain hotel. Part of the on-the-money Kimpton range, the boutique bolthole has oodles of urban character, arty rooms and if you sign up to their Kimpton Karma rewards before you land you’ll also get a $10 raid-the-mini-bar credit. Rooms from $180;


Thomas flew with Aer Lingus, which flies from Dublin to all three gateways and flies from Shannon to Boston and New York. Fares start from €438 return. N.B. Don’t forget baggage allowances (23kg checked and 10kg carry-on) and leave room for your return leg.

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