1/5

2015 GUIDE TO HOLIDAY SHOPPING IN CHICAGO

Read our holiday shopping guide for the best stores in Chicago, including downtown malls, suburban outlets, Christmas markets and more.

Back to Previous Page

Find the best shopping in Chicago, no matter who's on your holiday gift list, with this year's holiday shopping guide. From outlet malls in Chicago suburbs to shopping downtown Chicago, there's plenty to find for label lovers and bargain hunters alike.

 

MICHIGAN AVENUE "THE MAGNIFICENT MILE"

The Magnificent Mile Chicago

The 900 Shops
Located at the north end of The Magnificent Mile shopping district, the 900 North Michigan Shops is a chic indoor shopping destination with 70 luxury stores such as Gucci, Montblanc, Coach, L.K.Bennett and Michael Kors, in addition to one of the best known department stores in the world, Bloomingdale's.

The Shops at North Bridge
Spread throughout six city blocks, shoppers can explore 50 stores, such as BOSS Hugo Boss, Sephora, MAC, Louis Vuitton and more, as well as a flagship Nordstrom and 20 restaurants including the massive Italian emporium Eataly, Joe's Stone Crab and The Purple Pig — all in the expansive North Bridge District.

Water Tower Place
With more than 100 shops, including Macy's and a flagship American Girl Place, this spectacular, eight-level mall offers an array of retail options across all price ranges (from American Eagle Outfitters and Abercrombie & Fitch, to Adidas and Banana Republic, Pandora and Swarovski), as well as dining, spas and more.

 

STATE STREET: SHOPPING CHICAGO'S LOOP

State Street Chicago

Macy's on State Street
A must-visit gem in Chicago, this nine-floor flagship offers up everything on your shopping list: perfume, jewelry, handbags, clothing, housewares, toys, and of course, Frango® chocolates. It is an anchor of the State Street shopping district and is particularly festive around the holidays with its famed window displays and 45-foot Great Tree. The architecturally-rich building is a National Historic Landmark, and boasts the first restaurant in a department store, The Walnut Room, which opened in 1907.

Block 37
This landmark development features exciting retailers such as Sephora and Zara, restaurants and specialty food stores like Magnolia Bakery and Au Bon Pain, plus The Chicago Design Museum, all in a beautiful five-story atrium. This shopping destination also touts direct access to the CTA Red Line and Blue Line. 

 

NEIGHBORHOOD SHOPPING

Lincoln Park neighborhood shopping

Andersonville
Home to the Swedish American Museum and one of the city's largest LGBT communities, this area is known for its diversity, especially when it comes to shopping. Forget chain stores; this neighborhood's commercial district is lined with independent boutiques and specialty shops like Scout, Milk Handmade and Andersonville Galleria.

Lakeview
Looking for hip gift ideas? Hit up one of Lakeview's vibrant commercial districts, located along Belmont Avenue, Lincoln Avenue, Southport Avenue, Clark Street, Halsted Street or Broadway Street, where you'll find vintage shops, esoteric book stores, alternative clothing boutiques and offbeat home décor.

Lincoln Park
For independent boutiques and high-end retailers, stroll down Armitage Avenue for a day of shopping. From upscale pet accessories to sophisticated home-décor stores to trendy fashion boutiques, this is the spot to shop for well-heeled gift recipients.

Lincoln Square
Old World charm abounds in this German neighborhood, where you'll find quaint shops like Merz Apothecary, Timeless Toys and Margie's Candies. When you're ready for a break from shopping, refuel in one of the cozy bistros or sausage shops.

Roscoe Village 
This casual neighborhood offers an welcoming mix of shopping centered on Roscoe Street. From vintage clothing stores to unusual knick-knack shops to upscale baby clothing, you'll find it all at this "village within a city."

Wicker Park/Bucktown 
Get an urban shopping fix in this stylish neighborhood, where high-end antique stores (see Pavilion Antiques, Pagoda Red, Revival) and fashion industry icons (e.g. Marc Jacobs, Levi's) are sidled alongside bohemian boutiques and eclectic art galleries, all along North, Milwaukee and Damon Avenue.

West Town
This eclectic community (it's comprised of the West Town, Noble Square, Ukrainian Village and East Village neighborhoods) offers up a mix of funky thrift stores and independent retailers along Division and Chicago Avenue, while around Grand Avenue, those with an eye for design should hit the furniture showrooms, antique shops and architectural salvage warehouses for unique finds.

 

DISCOUNT OUTLET MALLS NEAR CHICAGO

Fashion Outlets of Chicago

Chicago Premium Outlets
With 120 outlet stores, such as Cole Haan, Michael Kors and Armani, deal hunters will be in shopping paradise while scoring discounts up to 65 percent off.

Fashion Outlets of Chicago
Do some deal hunting at this retail complex, where stores like Aldo, Nike and Bath & Body Works are interspersed between upscale bargain shops like Neiman Marcus Last Call and Saks Avenue Off 5th and luxury labels like Gucci and Prada.

Pleasant Prairie Premium Outlets
This retail outlet in Wisconsin promises 90 stores offering impressive savings. You'll find everything from Banana Republic and Hugo Boss to J. Crew and Nike.

 

HOLIDAY MARKETS & SHOPPING EVENTS

Christkindlmarket Chicago


  • Christkindlmarket
    November 20-December 24, 2015
    Deck the halls after a trip to this annual outdoor market, which celebrates the holiday season with German American traditions. Buy ornate, hand-blown glass ornaments, gorgeous nutcrackers, charming cuckoo clocks and other wooden handicrafts. You also can sip on hot, spiced wine, nosh on sausages and potato pancakes and sample many other German holiday delicacies.

  • Randolph Street's Holiday Market 
    November 21-22; November 28-29; December 12-13, 2015
    Antique shoppers will love this one-of-a-kind market, where fabulous finds are at every beautifully-curated corner. Browse memorable keepsakes, timeless antiques, vintage furs, estate jewelry and more at this posh event.  

  • One of a Kind Show
    December 3-6, 2015
    Peruse the handmade wares of more than 600 artists and makers at the mammoth Merchandise Mart. While you're there, catch an exciting artist demonstration, watch a fashion show or even create something original at a crafting workshop. 

  • Late Night Andersonville
    December 4; December 18, 2015
    From 6-10 pm, you even can save money on your holiday shopping when more than 40 stores and restaurants will offer extended hours, great deals and free refreshments throughout the neighborhood.

  • Julmarknad
    December 5-6, 2015
    Travel to Sweden — or as close as you'll get to it in Chicago — with this annual Swedish American festival, where shoppers can stock up on traditional handicrafts and delight in free performances, such as Nordic folk dancing and Swedish choir recitals.

  • Renegade Craft Fair Chicago Market 
    December 5-6, 2015
    Head over to the Bridgeport Art Center for this festive holiday market, where more than 100 independent designers and artisans will be showing off their handmade jewelry, one-of-a-kind clothing, funky accessories, unique stationary and more.

Featured Partners
Book a Trip
Find Hotels In
Check In
Check Out
Rooms
Travelers
From
To
Depart
Return
Travelers
Flying From
Find Packages In
Check In
Check Out
Rooms
Travelers
From
To