On a Saturday at Winterland it costs $24 before tax to skate, counting $8 for the rink and $16 for rentals. On a Monday it costs $12, as long as your address is in one of four zip codes. Winterland at Gallagher Way opens tomorrow, Friday, Nov. 20. That price gap shows how Lakeview's holiday season works: it runs on two calendars. One is built for visitors who come to Clark and Addison on weekends. The other is priced for people who live close enough to walk over on a Tuesday after work.
The second calendar is the cheaper one, and it isn't only at the rink. Two of the neighborhood's own chambers schedule local-only deals and events around the Wrigley crowd, and on the first weekend of December everything happens at once.
Two prices for the same ice
Winterland at Gallagher Way runs from Nov. 20 through Thursday, Dec. 31. Entry to the plaza and to Christkindlmarket Wrigleyville is free, with no tickets required. The rink, the Holiday Train and the market's food and merchandise are paid on site.
The neighbor rate is listed under "Neighbor Nights." Residents of 60613, 60614, 60640 and 60657 get rink admission for $4 a person and skate rentals for $8 on Mondays and Tuesdays. Gallagher Way notes that its attraction prices don't include tax, so the totals below are pretax.
| Regular price | Neighbor Nights, Mon. and Tue. | |
|---|---|---|
| Rink admission | $8 | $4 |
| Skate rental | $16 | $8 |
| One skater, rental included | $24 | $12 |
| Four skaters, rentals included | $96 | $48 |
The discount halves the price, and it lands on the two nights the plaza keeps its shortest regular hours. Monday through Thursday, Winterland runs 3 to 9 p.m. Fridays and Saturdays it opens at 11 a.m., and Sundays it runs 11 a.m. to 7 p.m. During the school break, it opens at 11 a.m. on Dec. 22, 23, 29 and 30. Dec. 22 and Dec. 29 are both Tuesdays, so those are the two Neighbor Nights with daytime hours.
The weeknight calendar has its own programming
Santa's Workshop, next to the Cubs Store, is open only on Fridays, Saturdays and Sundays, from Nov. 27 through Dec. 20. Pets are welcome on Sundays. Families who want Santa photos will be on the weekend calendar no matter what.
The rest of Gallagher Way's dated events are on weeknights:
- Thursday, Dec. 3, 10 and 17, 7 p.m.: movie nights on the plaza.
- Tuesday, Dec. 8, 5:30 p.m.: the JCC's annual menorah lighting for the fifth night of Hanukkah. That's a Neighbor Night, so the $4 rink rate applies the same evening.
- Regular Monday through Thursday hours: the plaza is open 3 to 9 p.m., except on Thanksgiving, Christmas Eve, Christmas Day and the school-break dates.
The market adds its own reason to come back. Block Club Chicago reported that the Wrigleyville market has 28 vendors this year. A mug marks Christkindlmarket's 30th anniversary, which counts from the original market, not from the Wrigleyville location. The Christkindlmarket Wrigleyville page lists its own hours, including 11 a.m. openings on Monday, Dec. 21, and Monday, Dec. 28, during the school break. Winterland is closed on Christmas Day.
The chambers have their own neighbor rate
Gallagher Way checks your zip code. Lakeview's business groups get a similar result by pricing in gift cards that only pay off if you shop the neighborhood all year.
On Saturday, Dec. 5, from 11 a.m. to 3 p.m., the Lakeview East Chamber of Commerce holds its Shoppers Extravaganza & Holiday Treat Stroll. Participating businesses hand out cookies, cocoa and savory samples. The bigger draw is the gift card sale, which the chamber describes this way:
"For one day only, shoppers can score 25% off Lakeview East Gift Cards, accepted at more than 200 neighborhood businesses. Purchases are limited to $500 per household."
A visitor gets little out of a discounted card they may never use again. Someone who already buys groceries, haircuts and takeout within walking distance of Broadway and Clark gets a quarter off spending they were going to do anyway.
West Lakeview runs its tradition on a Sunday night. The West Lakeview Tree Lighting is Sunday, Nov. 22, 6 to 7:30 p.m., where Lincoln, Southport and Wellington meet outside St. Alphonsus. This year's event includes a houseware, toy and book drive for the Chicago Furniture Bank.
Dec. 4 to 6 is when the two calendars overlap
For most of the season, the visitor calendar and the neighbor calendar stay out of each other's way. On the first weekend of December they stack up.
| Date | Event | Where |
|---|---|---|
| Fri., Dec. 4, 6 p.m. | Winterland Tree Lighting Ceremony, which Gallagher Way calls its official kickoff, with local musical performers and giveaways | Gallagher Way, 3635 N. Clark St. |
| Fri., Dec. 4, evening | Southport Holiday Cocktail Crawl, with tickets from $33.85 | Check-in at 1409 W. Addison or Sheil Park, 3511 N. Southport |
| Sat., Dec. 5, 11 a.m. to 3 p.m. | Shoppers Extravaganza & Holiday Treat Stroll, with the 25% gift card sale | Lakeview East businesses |
| Sat., Dec. 5, into Sun., Dec. 6 | Roscoe Village Neighbors Winterfest | Roscoe Village |
| Sun., Dec. 6 | Annual Lakeview Menorah Lighting Ceremony, organized by the Chabad of Lakeview | Lincoln & Marshfield |
Friday evening is the tight spot. The Gallagher Way tree lighting and the Southport Holiday Cocktail Crawl overlap, and the crawl's Addison check-in is a short walk from the plaza. The crawl includes cocktail samples along the Southport corridor, carolers and Santa photos. Doing both means lighting first and crawl second, or the other way around. Saturday is easier: the Lakeview East gift card window closes at 3 p.m., and the Roscoe Village Winterfest details are on the Roscoe Village Neighbors event page.
The Sunday menorah lighting at Lincoln & Marshfield is funded by Special Service Area 27, the same local district behind the West Lakeview tree lighting. Details are on SSA 27's ceremony page.
The bars stay open past the rink season
Winterland ends Dec. 31. Wrigleyville Wonderland, the Lakeview East Chamber's holiday program, has participating businesses running themed spaces from as early as Nov. 1 through Jan. 31, 2027. The Wrigleyville Wonderland guide counts more than 25 holiday-themed bars.
A few on the list:
- Holly Dolly Honky Tonk at Big Star Wrigleyville, a new Dolly Parton theme for the pop-up's third straight year, opening Nov. 20.
- Elf'd Up at Stretch.
- Christmas at Kincade's.
- Santa Baby Bar at Stolen Saddle.
- Mistletoe at Mordecai, which is back this year.
Across the plaza, Alma at Hotel Zachary takes reservations starting in December for Globes on the Terrace, a globe on Alma's terrace with mulled wine, board games, s'mores and vinyl records. Bookings are on OpenTable.
Saturday, Dec. 12, is a milestone for the visitor calendar. Block Club Chicago reported that this year's TBOX bar crawl is the last one founder Christopher Festa will lead, after 30 years. It starts at 10 a.m. at The Cubby Bear, 1059 W. Addison St., and is 21-and-over and ticketed. For anyone planning a Saturday errand near Clark and Addison, that date is now on the calendar.
Some storefronts will change by the time the rink closes
The neighbor calendar also includes the shops people walk to the rest of the year, and a few are changing this season.
Southport Grocery & Cafe, at 3552 N. Southport, is set to close Dec. 31 after 23 years, the same day Winterland ends. The Southport Corridor weekly roundup reports that Dollop Finer Diner plans to open in the space on Feb. 1, 2027, after renovations in January. The same roundup reports that the chamber welcomed Fly is Fundamental, a luxury streetwear shop, to 3774 N. Clark St.
On Broadway, Royal Home Entertainment closed its storefront on Oct. 17 after 55 years. The Lakeview East Chamber reports that owner Joe DeGuide will continue the business online and offer AV consulting. A few blocks away, Unabridged Bookstore at 3251 N. Broadway is staying open: its founder is selling the shop to longtime manager Shane Khosropour. It's one more place where a discounted Lakeview East gift card can be spent come January.
If you want to know how your block's businesses and buildings are shifting heading into 2027, Sullivan Property Group tracks Lakeview at that same block-by-block level. Schedule a Consultation, and Tim will walk you through what's changing near you.
