Winterland at Gallagher Way opens tomorrow, Friday, Nov. 20, and runs through Dec. 31. Its published schedule sorts the season by day of the week. Mondays and Tuesdays carry a discount for the zip codes around the ballpark. Thursdays in December bring free movies. Most of the reserved and ticketed family events fall on Friday through Sunday.
Everyone gets in free. Christkindlmarket Wrigleyville sits inside Winterland at 3635 N. Clark St., and no ticket is needed for either one. Prices only differ for the extras, and that is where Lake View's own discount applies.
The Price List Has a Zip Code Line
The Gallagher Way Winterland page lists standard 2026 prices of $8 for Gallagher Ice Rink access and $16 for skate rental. Skaters can also bring their own skates. The same page offers Neighbor Discount Nights on Mondays and Tuesdays. Residents of 60613, 60614, 60640 and 60657 pay $4 per person for admission and $8 for skate rental.
The discount adds up quickly for a household. Four people renting skates on a Saturday pay $96 before tax. The same four pay $48 on a Monday. Gallagher Way says attraction prices do not include tax and are subject to change.
From opening day through Dec. 31, the calendar has 12 Mondays and Tuesdays: Nov. 23, 24 and 30, and Dec. 1, 7, 8, 14, 15, 21, 22, 28 and 29. Those are the dates the zip code pricing applies.
A Week at Gallagher Way, Day by Day
Winterland and the market keep the same regular hours. They open at 3 p.m. Monday through Thursday, so weekday visits start after school and after work.
| Day | Hours | What the schedule adds |
|---|---|---|
| Monday | 3 to 9 p.m. | Neighbor Discount Night: $4 admission, $8 skate rental |
| Tuesday | 3 to 9 p.m. | Neighbor Discount Night, plus the Dec. 8 menorah lighting |
| Wednesday | 3 to 9 p.m. | Regular pricing |
| Thursday | 3 to 9 p.m. | Free holiday movies on the video board, Dec. 3, 10 and 17 |
| Friday | 11 a.m. to 9 p.m. | Santa's Workshop from 4 to 9 p.m., starting Nov. 27 |
| Saturday | 11 a.m. to 9 p.m. | Santa's Workshop from 11 a.m. to 5 p.m., Alma's Breakfast with Santa and Teddy Bear Tea |
| Sunday | 11 a.m. to 7 p.m. | Santa's Workshop with pets welcome, Alma's weekend events |
The holidays change a few of these hours. Thanksgiving, Nov. 26, runs from 11 a.m. to 4 p.m., and so does Christmas Eve. Christmas Day is closed. Gallagher Way opens at 11 a.m. on Dec. 22, 23, 29 and 30 for winter break. Christkindlmarket's Wrigleyville schedule also lists 11 a.m. openings on Monday, Dec. 21 and Monday, Dec. 28. On Gallagher Way's schedule, two of the 12 neighbor nights, Dec. 22 and Dec. 29, fall on those 11 a.m. winter break days, so the discount rink is open from late morning.
The Free Nights Are Dated
Winterland charges nothing for its set-piece events. Each one has a single date, and most fall on a weekday:
- Thursday, Dec. 3, 7 p.m.: "Dr. Seuss' How the Grinch Stole Christmas" on the Gallagher Way video board, the first of three Toyota Movie Nights.
- Friday, Dec. 4, 6 to 8 p.m.: The Winterland Tree Lighting Ceremony, with the Dartmouth Decibelles and a Goodman Theatre performance from "A Christmas Carol." The event listing promises free hot cider to the first 500 guests.
- Tuesday, Dec. 8, 5:30 p.m.: JCC Chicago's "Fifth Night, Fifth Light" menorah lighting for the fifth night of Hanukkah. It falls on a neighbor night.
- Thursday, Dec. 10, 7 p.m.: "The Santa Clause."
- Thursday, Dec. 17, 7 p.m.: "The Muppet Christmas Carol."
Combined with the Monday and Tuesday pricing, this gives neighbors at least three discounted or free nights in most December weeks without touching a weekend.
Weekends Are Built Around Reservations
Most of the scheduled family events land on Friday through Sunday. Santa's Workshop sits next to the Cubs Store and runs Nov. 27 through Dec. 20. Hours are 4 to 9 p.m. on Fridays and 11 a.m. to 5 p.m. on Saturdays and Sundays. Pets are welcome on Sundays, and Gallagher Way's FAQ says Santa wears a pet-friendly suit for those visits. An on-site photographer sells photos, and families can use their own cameras.
Across Clark, Alma at Hotel Zachary, 3630 N. Clark St., holds Breakfast with Santa on Saturdays and Sundays from Nov. 29 through Dec. 20. Teddy Bear Tea follows on weekends from Dec. 5 through Dec. 27. Alma's Globes on the Terrace are the exception to the weekend pattern. These private globes come with mulled wine, board games, s'mores and vinyl records, and reservations open daily starting in December.
The wreath workshops are also weekend-only. Indigo & Violet Studio teaches them on Saturday, Dec. 5 and Sunday, Dec. 6, at 11 a.m. or 1:30 p.m., in The Events Center at Wrigley Field, 1101 W. Waveland Ave. The cost is $62 for adults 18 and older, a wreath and materials are included, and reservations are required. The $5 Holiday Train runs through the Wrigley Field concourse whenever Winterland is open, with a 36-inch height minimum.
Anyone coming by car will find the Toyota Camry lot at 1126 W. Grace St. starting at $15. VIP parking at the Toyota Highlander lot, 1088 W. Waveland Ave., starts at $30.
The Market Inside Marks a 30th Year
Christkindlmarket Wrigleyville has 28 vendors this year. Block Club Chicago reported that 2026 is Christkindlmarket's 30th anniversary season, which comes with special-edition mugs. Choose Chicago's market guide describes the collection: a pearl-finish flute-shaped mug with market and fireworks artwork, a green tree mug decorated with miniature ornaments, a ceramic beer stein, and a new mini stein shot cup.
The Bars Around the Ballpark Run Their Own Season
The blocks around Gallagher Way follow the same calendar, and several holiday pop-ups match Winterland's dates almost exactly:
- Mistletoe at Mordecai: Opens Nov. 20 with Winterland and runs through Jan. 3, with a limited holiday cocktail and food menu.
- Holly Dolly Honky Tonk at Big Star Wrigleyville: Tuesday, Nov. 24 through Monday, Jan. 4. In its third consecutive year, the pop-up has a new theme honoring Dolly Parton.
- Lucky Lodge at Lucky Dorr: Open seven days a week with extended hours during Winterland. It serves seasonal beers and hot cider, welcomes dogs, and runs holiday card collecting in Caretakers Way.
- Kincade's Wrigley, 3660 N. Clark St.: Block Club Chicago covered the bar's expansion to Wrigleyville, 40 years after the original opened in Lincoln Park. Its first Christmas season on Clark started Nov. 10 and includes rooftop holiday movies and trivia on Wednesdays.
Kincade's Wednesday programming fills the one weeknight Winterland leaves open. With that, every weeknight on this stretch of Clark has its own draw.
Two more of this year's arrivals are a short walk south. Level Sporting Club, a bar devoted to women's sports at 3343 N. Clark St., opened June 4, according to GO Magazine. Hattie B's Hot Chicken opened its first Chicago location at 3649 N. Clark St. early this year, as the Lakeview East Chamber of Commerce noted in its March roundup of new businesses.
The Last Week Is Wrigleyville's Alone
The two city markets end on different dates. Block Club reported that the Daley Plaza market runs through Christmas Eve, while the Wrigleyville market stays open through New Year's Eve. From Dec. 26 through Dec. 31, Gallagher Way is the only Christkindlmarket in Chicago. That stretch includes neighbor nights on Monday, Dec. 28 and Tuesday, Dec. 29, and Gallagher Way opens at 11 a.m. on Dec. 29 for winter break. The season closes on Thursday, Dec. 31, with an 11 a.m. to 4 p.m. day.
The block will look different by next winter. Portillo's has announced a location at 3519 N. Clark St. with the chain's first walk-up window, and Block Club reported an expected opening in 2027.
Living a few blocks from Gallagher Way means both the ballpark's off-season and game days shape life on your street. If you are weighing how that plays out on a particular block in 60613 or 60657, Jason O'Beirne and his team can go through it with you street by street. Schedule a consultation.
