Posted November 12, 2020

The Best Holiday Markets in Chicago, Milwaukee & Cleveland


The holiday season means pop-up markets—all ideally situated in the most dazzling neighborhoods. In the Midwest, local markets are just as much about providing a totally immersive experience as they are about finding the perfect gifts. Think local food, live music and a true party atmosphere. Here are our top picks.


MUST GO: Christkindlmarket Chicago

christkindlmarket chicago

Nothing says holiday cheer quite like the festive glow of a giant Christmas tree. Image Credit: Christkindlmarket Chicago.

The vibe: This traditional German market has row after row of glowing tiny timber cabins nestled under the shadow of a 70-foot-tall Christmas tree. Each cabin holds gifts and food from a local or international vendor.

The goods: Browse everything from oompah-party-ready steins to handmade wooden nutcrackers to chocolates and cheeses.

christkindlmarket sweet castle photo credit kameron sears

Make sweet holiday memories at Christkindlmarket. This traditional German Christmas market has locations in Chicago and Milwaukee, among others. Image Credit: Kameron Sears.

The highlights: Frank’s Ornament House has hundreds of baskets filled with hand-blown baubles of every shape, style and theme. For food, the Kimpton Gray and Kimpton Journeyman hotels will have pop-up booths on November 28 featuring macaroons by Executive Chef Brian Millman of the Kimpton Gray’s restaurant and bar concepts, Vol. 39 and Boleo.

The location: Daley Plaza, 50 W. Washington St. in the Loop, just west of the famous State Street shopping strip.

The deets: Open daily, November 15 thru December 24. Admission is free.

ALSO TRY: One of a Kind Holiday Show

The vibe: This super-busy but refined gallery experience is held indoors across several showrooms. The cool thing is that you can usually meet the artist who created the unique and gift-able wares you’re being tempted by.

ceramic planters on display from a vendor image credit chicagoone of a kind holiday show

Shopping local never looked so good. Image Credit: Chicago’s One of a Kind Holiday Show.

The goods: A highly curated and expressive array of ceramic kitchenware, recycled paper home decorations, handcrafted artwork and jewelry, and more – all created by more than 600 independent artists from across the country and beyond.

one of a kind holiday show

Gift a piece with a story at Chicago’s One of a Kind Holiday Show, where you can meet the local artisans and designers behind each object. Image Credit: Chicago’s One of a Kind Holiday Show.

The highlights: You’ll love the merchants selling Chicago-centric gifts, like prints of the “El” train by Cape Horn Illustration and Chicago flag runners and napkins by Made by Cat Painter.

The location: The Mart, 222 W. Merchandise Mart Plaza in River North along the Chicago River.

The deets: Held December 6-9. Tickets are $12; kids 12 and under are free.

Where to stay in Chicago: The Kimpton Gray Hotel is located near both markets in the Loop and is offering a special Christkindlmarket package.


MUST GO: Christkindlmarket Milwaukee

The vibe: Milwaukee is getting their own sister market to the Christkindlmarket in Chicago and Naperville. Expect the same whimsy and flair, from the pretty timber cabins to the ceramic mugs from which you can sip traditional glühwein (hot mulled spiced wine).

The goods: There are lots of gifts to keep you warm and cozy all winter. Think fuzzy alpaca sweaters, hand-knit scarves and Belgian hot chocolate.

The highlights: Enjoy live music from the Alpine Brass Trio Band every Saturday and Sunday as they perform holiday favorites and German carols.

The location: Fiserv Forum, 1111 N. 4th St., just west of Old World Third Street.

The deets: Open daily November 15 thru December 24. Admission is free.

ALSO TRY: Cream City Creatives Craft Fair

The vibe: Milwaukee’s nickname is Cream City because of the special cream-colored bricks used in a lot of historic buildings. You’ll feel that distinct local flair and creative spirit as you walk aisles and aisles of gifts, apparel, home goods, food and more.

The goods: They’re all handmade – and all from Milwaukee. Expect screen-printed greeting cards, knit sweaters, wall art, soaps and other finds that are sure to make you Gifter of the Year.

teas at tippecanoe herbs cream city creatives image credit tippecanoe herbs courtesy ofcream city creatives

Sustainable, organic holiday gifts handmade by Milwaukee locals? Yes, please! Image Credit: Tippecanoe Herbs, courtesy of Cream City Creatives.

The location: Turner Hall Ballroom, 1040 N. 4th St.

The deets: Held Sunday, November 24. Admission is free.

Where to stay in Milwaukee: The Kimpton Journeyman Hotel, located in the heart of the Third Ward, close to both markets.


MUST GO: The Cleveland Bazaar Holiday

The vibe: Four floors of artisans and food purveyors showcase Cleveland’s creative streak. Shop, eat and chat with the vendors, who take a lot of pride in their craft and the city’s growing arts and culinary scene.

cleveland bazaar holiday image credit cleveland bazaar

With four floors of shopping at The Cleveland Bazaar, you’ll surely check everyone off your list. Image Credit: Cleveland Bazaar.

The goods: Candles for your best friend. Ceramics for that special someone. A knit hat for, well…just about anyone. Find it all here, plus an array of local food and drinks to keep your stamina up.

The location: 78th Street Studios, 1305 W. 80th St.

The deets: Held December 14-15. Admission is free.

ALSO TRY: North Union Farmers Market Holiday Market

The vibe: In true farmers market style, this one-day event features a simple but charming setup of tables run by local farmers and makers. It’s a great place to do a quick gift-shopping blitz.

The goods: Ohio produce, fruit and baked goods are staples. But there’s also a focus on gifting, with handcrafted earrings, wooden coasters, scented soaps and more – many for under $20.

The location: 13209 Shaker Square

The deets: Held Saturday, December 7, 4 – 8pm  and Saturday, December 14, 10am – 4pm. Admission is free.

Where to stay in Cleveland: The Kimpton Schofield Hotel, located in a landmark downtown Cleveland building.

—Kelly Aiglon


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