From the blog

Guide to Holiday Shopping in Chicago

It’s that time of year when wallets get a little thinner and shopping bags get a little fatter, the holiday shopping season is here. With everyone rushing around to find the perfect gift, it is helpful to know the best spots to find what you are looking for. From upscale shopping along Michigan Ave. to unique holiday markets, there are opportunities for everyone’s Christmas shopping list.

Shop till you drop by using our guide to the best holiday shopping in Chicago.

Michigan Ave. – “The Magnificent Mile”

When people think “shopping in Chicago” they usually have visions of The Magnificent Mile, in their heads. This well-known street in downtown Chicago is home to numerous shops, restaurants, and cafés. Decked out for the holidays, Michigan Ave. offers some of the best upscale shopping in the city.

900 North Michigan Ave. Shops
Located at the north end of the street, the 900 North Michigan Ave Shops is a swanky indoor shopping destination with over 60 high-end retailers such as Gucci, St. Croix, Kendra Scott, and many more.

The Shops at Northbridge
This oversized shopping mall located in the North Bridge District offers over 50 stores such as a flagship Nordstrom, Keihl’s, and Alex and Ani. Plus, shoppers can choose from over 20 restaurants like Joe’s Stone Crab and California Pizza Kitchen.

Water Tower Place
The eight-level shopping destination at Water Tower Place offers visitors an array of shopping opportunities from Abercrombie and Fitch to Swarovski. With dining, spas, and various events it is easy to see why this is one the best spots for holiday shopping in Chicago.

Shop the shops on State Street

Expand your search beyond Michigan Ave. and head to State Street. Home to the ever-so-popular Macy’s nine-story flagship store, plus other favorites like H&M, Zara, and Forever 21. Cross the street and discover Block 37, an eclectic mix of retailers and restaurants in a five-story shopping mall.

Located on State Street, a stay at The Penthouse at Grand Plaza is the best way to take advantage of holiday shopping in Chicago.

Holiday markets

Chicago is a great place to be during the holidays, especially for your Christmas shopping needs. Part of what makes holiday shopping in Chicago so unique are the many holiday markets and events happening in the city.

ChristkindmarketNov. 16 – Dec. 24, 2018
Annual outdoor holiday market, celebrating the holiday season with German-American traditions.

Millennium Park Holiday Art MarketNov. 16 – 18, 2018
Support local art through this one-of-a-kind holiday market. Shop handmade goods from more than 150 art students from the School of Art Institute of Chicago.

Randolph Street’s Holiday MarketNov. 17 – 18; Dec. 15 – 16, 2018
Looking for a truly unique gift, unearth hidden gems like timeless antiques, vintage furs, and estate jewelry.

Renegade Craft FairDec. 1- 2, 2018
More than 100 independent designers and artists showcasing their handmade jewelry, clothing, and eclectic accessories.

One of a Kind ShowDec. 6 – 9, 2018
Shop handmade goods from over 600 vendors at the Merchandise Mart at this annual show.

Shop local neighborhoods

Surrounding Chicago are many cozy and quaint neighborhoods that offer unique and charming shopping opportunities.

Lincoln Park
Not a shopping mall person? Enjoy, the charming tree-lined streets of Lincoln Park with shops in Victorian row houses.

For that hipster in your life, head to the ever so hip neighborhood of Lakeview. Find vintage shops, cozy bookstores, and unique clothing boutiques.

Wicker Park/Bucktown
An urban shopping experience in a stylish neighborhood where premium antique stores and bohemian boutiques meet.

Recognized for its diversity, Andersonville offers shoppers a mix of thrift stores and independent retailers.

Outlet malls near Chicago

If you are looking for a deal this holiday season, expand your shopping search to nearby outlet malls outside of the city. Chicago Premium Outlets, Fashion Outlets, and Pleasant Prairie Premium Outlets all offer bargain shoppers impressive savings.

Stay in a luxurious Chicago Penthouse

Style and comfort meet at The Penthouse at Grand Plaza. Enjoy the best views of the city from your own luxurious penthouse in downtown Chicago. We offer nine different penthouses, all designed to offer everything you need and more during your vacation.

Browse our available accommodations and start planning your holiday vacation to Chicago!


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