Chicago's holiday shopping runs from a German market downtown to a parade of lights on Michigan Avenue and neighborhood nights when local shops stay open late. Here is what organizers have confirmed for 2026 as of mid-October, what to buy and which shops are nearby. Where a 2026 date isn't posted, we give last year's format.
Christkindlmarket Chicago: Daley Plaza and Wrigleyville
The Christkindlmarket marks its 30th anniversary in 2026, according to NBC Chicago's August announcement. The downtown market at Daley Plaza (50 W Washington St) opens Friday, Nov. 20 and runs daily through Dec. 24. Hours are 11am to 8pm Sunday to Thursday and 11am to 9pm Friday and Saturday, with 11am to 4pm on Thanksgiving (Nov. 26) and Christmas Eve. Admission is free.
Vendors sell German food and drinks, handcrafted toys and gifts; Fox 32's 2025 preview listed roasted nuts, bratwurst and hot spiced wine. Organizers have told visitors in past years to bring cash, since many vendors don't take cards.
The market is a short walk west of State Street along Washington Street, so pair the two. Macy's on State Street (111 N State St) has its Holiday Square market on the 7th floor (Nov. 20 to Dec. 24, Thursdays to Sundays, per Macy's store page), Barnes & Noble State Street (150 N State St) covers books and gifts on three floors, and Target State Street (1 S State St) handles the practical list.
The Wrigleyville market at Gallagher Way (3635 N Clark St) runs Nov. 20 to Dec. 31, per the market's own site, as part of Winterland at Gallagher Way. Weekday hours start at 3pm, weekends at 11am, and it closes on Christmas Day. The Southport shops are a few blocks from Wrigley Field: Paper Source (3543 N Southport Ave) for stationery, cards and gifts, Kendra Scott (3426 N Southport Ave) for jewelry with free engraving, and ThirdLove (3539 N Southport Ave) for bra fittings.
Magnificent Mile Lights Festival: Saturday, Nov. 21
The Magnificent Mile's own site lists the 2026 Lights Festival for Saturday, Nov. 21. Lights Festival Lane runs 11am to 4pm with live entertainment and family activities. The parade starts at 5:30pm at Oak Street and Michigan Avenue and heads south along the avenue as one million lights come on in more than 200 trees. The Wintrust Fireworks Spectacular follows at 7:30pm over the Chicago River at Michigan Avenue. Street closures can start as early as 3pm.
Shop before the crowds gather. Harry Potter Shop Chicago (676 N Michigan Ave) sells a Chicago-only bear, spirit jersey, pins and mug that are in-store only, and stays open to 9pm on Saturdays. Hotel Chocolat (830 N Michigan Ave) has boxed chocolates and bars for stocking stuffers. In Water Tower Place, the LEGO Store (835 N Michigan Ave, Unit 3000) and American Girl Place (835 N Michigan Ave) cover the kids' list, but the mall closes at 8pm on Saturdays. For a warm-up after the fireworks, the Starbucks Reserve Roastery (646 N Michigan Ave) stays open to 9:30pm on weekends. The Purple Pig (444 N Michigan Ave) is a dinner option near the river.
Andersonville: Julmarknad and Late Night Andersonville
The Swedish American Museum (5211 N Clark St) hosts Julmarknad, its holiday market, with neighborhood groups. The museum hasn't posted 2026 dates yet. In 2025 it ran over the first weekend of December, with a Friday-evening preview sale, Saturday 10am to 5pm and Sunday 10am to 4pm. Expect Scandinavian and modern handicrafts, from vendors such as Dala Ceramics, and Swedish treats. The chamber's Late Night Andersonville, in December, keeps Clark Street shops open into the evening with sidewalk pop-ups from 4 to 8pm and roasted chestnuts.
The shops along Clark make this the best neighborhood for Chicago-made gifts. Andersonville Galleria (5247 N Clark St) gathers more than 100 local makers under one roof and opens at 11am daily. Transit Tees (5226 N Clark St) turns CTA maps and city flags into shirts as an official CTA licensee, and Strange Cargo (5216 N Clark St) prints Chicago tees. Paper & Pencil (5208 N Clark St) sells pens, notebooks and planners; it is cashless, so bring a card. *play (5311 N Clark St) is for toys and kids' books. Lost Larson (5318 N Clark St) bakes cardamom buns and princess cake, and Gethsemane Garden Center (5379 N Clark St) sells Christmas trees each December.
Lincoln Square: Wine Stroll, Small Business Saturday and Shop Late
The Lincoln Square Ravenswood Chamber lists its Fall Wine Stroll for Thursday, Nov. 12, 2026, 6 to 9pm, as the kick-off to holiday shopping. Each year on the Saturday after Thanksgiving, the chamber turns the strip into a holiday market for Small Business Saturday, with a tree lighting. Its Shop Late evenings, when stores stay open 5 to 8pm with refreshments, specials and pop-ups, ran on two December Thursdays in 2025; 2026 dates aren't posted yet.
Timeless Toys (4749 N Lincoln Ave) stocks wooden toys, puzzles and LEGO. The Chopping Block (4747 N Lincoln Ave) and Savory Spice Shop (4753 N Lincoln Ave) cover cooks; The Chopping Block's store is open Wednesday to Saturday only. Merz Apothecary (4716 N Lincoln Ave) sells European skincare, Midwest Nice (4619 N Lincoln Ave) carries work by more than 100 mostly Chicagoland makers, and The Book Cellar (4736-38 N Lincoln Ave) is an independent bookstore with a cafe. Pick up smoked meats and imported beer at Gene's Sausage Shop (4750 N Lincoln Ave), or sit down at Bistro Campagne (4518 N Lincoln Ave) for onion soup.
Worth Watching: One of a Kind Holiday Show
Event listings put the 2026 One of a Kind Holiday Show at The Merchandise Mart from Dec. 3 to Dec. 6, with hundreds of fine art and craft sellers. We couldn't load the organizer's own page, so confirm there before you go.
Daley Plaza: The Lake Red Line subway stop is the closest. The elevated State/Lake station closed in January 2026 for rebuilding, so on the Loop 'L' use Washington/Wabash or Clark/Lake. Wrigleyville: The Southport Brown Line stop is in the middle of the Southport shops. Magnificent Mile: Take the Red Line to Grand or Chicago and walk two blocks east; expect street closures from 3pm on festival day. Water Tower Place and 900 North Michigan Shops both have self-parking and valet.
Andersonville: Take the Red Line to Berwyn or Bryn Mawr and walk west to Clark Street, or ride the #22 Clark bus, which runs along the shopping stretch. Lincoln Square: The Western Brown Line stop is at Western and Leland, a block from Lincoln Avenue. Both neighborhoods have metered street parking on the main street and side streets.
