①
Ukrainian Village / Wicker Park / Bucktown
"Murals, Margaritas & the Soul of the City"
Culinary & Spirits Tour
1
11am — Warm-up
TRUCE
1935 N Damen Ave, Bucktown · Opens 8am
Coffee-to-cocktail concept, 4.9★. Seasonal craft drinks, owner-operated, intimate. The perfect way to ease into the day before shopping opens up.
⭐ Unique spot
2
12pm — Lunch
Big Star
1531 N Damen Ave, Wicker Park
Chicago's most iconic taco bar. Birria tacos, spicy margaritas, a legendary bar patio. This is Wicker Park distilled into a single experience. Bar TVs for game viewing.
🍽 Lunch📺 TVs
3
2:30pm
Desert Hawk
2049 W Division St, Ukrainian Village
Possibly Chicago's best smash burger alongside Filipino-inspired street food by Chef David. Craft cocktails, 4.7★, deep neighborhood credibility. The real surprise of the afternoon.
⭐ Unique spot
Shopping
Una Mae's
1528 N Milwaukee Ave — Curated indie clothing and accessories, whimsical but well-designed. Opens 12pm.
AKIRA
1814 W North Ave — Elevated women's fashion, shoes, and accessories. Opens 11am.
Penelope's
1913 W Division St — Women's boutique + home goods. Vibrant, eclectic, very neighborhood.
Flatiron Arts Building
1579 N Milwaukee — Chicago's version of the NYC Flatiron. Independent artist studios — great walk-through.
Activities
Featured activity
WhirlyBall
1825 W Webster Ave, Bucktown
Bumper cars meets lacrosse — teams compete head-to-head in enclosed courts. The most fun group activity in Chicago for competitive types. Full bar, referees, 60–90 min sessions. Fully indoors and heated, ideal for December.
Ukrainian Institute of Modern Art ✦ Bonus
2320 W Chicago Ave · $5 · Wed–Sun noon–4pm
Intimate gallery space, 4.8★. Rotating exhibits in a beautifully restored historic space. A genuine discovery — not tourist Chicago. Pairs naturally with the Desert Hawk stop nearby.
December note: Division St and Damen Ave are beautifully lit. The six-corners at Milwaukee/North/Damen is one of Chicago's best holiday photo spots. WhirlyBall is heated — ideal for a cold December afternoon.
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②
Lincoln Park / Armitage Avenue
"Chicago's Most Beautiful Block, Dressed for Christmas"
Culinary & Spirits Tour · ★ All stops YPO Member Owned — Lettuce Entertain You
1
11am — Lunch
Café Ba-Ba-Reeba
2024 N Halsted St, Lincoln Park
Lettuce's beloved Lincoln Park tapas institution since 1982. Crispy patatas bravas, world-class sangria, and a buzzing social scene that has packed tables for over 40 years.
🍽 Lunch★ YPO Member Owned
2
1:30pm
R.J. Grunts
2056 N Lincoln Ave, Lincoln Park
The very first Lettuce Entertain You restaurant, open since 1971. Legendary burgers, an iconic salad bar, and the easy neighborhood energy that started it all.
★ YPO Member Owned⭐ First LEYE restaurant
3
3pm
Summer House Santa Monica
1954 N Halsted St, Lincoln Park
California-casual all-day dining with a beautiful airy interior. Farm-fresh salads, fish tacos, and house cocktails. The best Lincoln Park afternoon drink stop.
📺 TVs★ YPO Member Owned
Shopping · Armitage corridor
art effect
934 W Armitage — Eclectic gifts, jewelry, and women's clothing. The anchor boutique of the strip. Opens 11am.
Peruvian Connection
925 W Armitage — Luxury Alpaca knitwear and timeless women's pieces. Premium quality, beautiful fabrics.
Lost Soul Found
1017 W Armitage — Boutique clothing + excellent house-made coffee. Shabby-chic, creative energy. Opens 10am.
The full Armitage strip
Halsted to Sheffield — Chicago's best walkable boutique mile. Home goods, jewelry, and independent cafés throughout.
Activities
Featured activity
Lincoln Park Zoo
2001 N Clark St · 15-min walk from Armitage
One of the last free zoos in the country. Winter is a wonderful time to visit — fewer crowds and the animal buildings are warm sanctuaries. A beautiful walk from the Armitage strip.
Chicago History Museum ✦ Bonus
1601 N Clark St · $25 · Open Sat 9:30am–4:30pm
Excellent and surprisingly engaging museum, 4.6★. Covers Chicago from the Great Fire to the 20th century. Adjacent to Lincoln Park Zoo — easy to pair both in the same afternoon.
December note: Armitage Ave between Halsted & Sheffield is Chicago's most picturesque block in December — brownstones, window boxes, and ivy all in holiday lights. All three Culinary & Spirits stops are Lettuce Entertain You — the family-owned restaurant group led by YPO Chicago member R.J. Melman. See Partner Spotlight below.
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③
Lakeview / Wrigleyville / Southport
"Cubs Country at Christmas — Where Ivy Meets Tinsel"
Culinary & Spirits Tour
1
12pm — Lunch · After Wrigley Tour
Little Goat Diner
3325 N Southport Ave · Reserve ahead
Stephanie Izard's Southport outpost — one of Chicago's most celebrated chefs. 4.7★ across 10,000+ reviews. Elvis pancakes, the patty melt, house cocktails. Reserve ahead — this fills up on Saturdays.
🍽 Lunch⭐ Celebrity chef
2
1:30pm
Toons Bar & Grill
3857 N Southport Ave · Opens 11am
Pure Chicago neighborhood sports bar. Legendary wings, walls of TVs, great beer selection. 4.5★, opens 11am. The kind of genuinely local spot that doesn't exist in River North — regulars, barstools, and game day energy every day.
📺 Best TVs on this route
3
3pm
Budweiser Brickhouse Tavern
3647 N Clark St, Wrigleyville
Right in Wrigley's shadow. 4.7★. Multiple TVs, classic Chicago dogs, solid apps. Walk out the door and the Friendly Confines is half a block north. The perfect Southport-to-Wrigleyville transition.
📺 TVs⭐ Wrigley-adjacent
Shopping · Southport corridor
Alice & Wonder
3542 N Southport — Chicago-themed boutique, 4.9★. Custom patch hats and locally-made gifts. The best "I was in Chicago" souvenir that doesn't look like airport merch.
Batik Chicago
3746 N Southport — Vibrant resort-wear boutique. Zimmermann-adjacent prints, owner-operated. Open Wed–Sat.
Southport Grocery & Café
3552 N Southport — Gourmet grocery and café. Exceptional pancakes, artisan pantry items worth browsing. Closes 3pm.
Bombastic Café
3732 N Southport — House-roasted coffee, indie art vibe. Perfect afternoon pitstop between boutiques.
Activities · Start at 10am before lunch
★ YPO Member Owned · Featured Activity
Wrigley Field Ballpark Tour
1060 W Addison St, Wrigleyville
The best 90-minute activity available to any Chicago visitor. Guided tours give access to the Cubs dugout, the warning track, the legendary ivy, and the press box. Consistently called a bucket-list experience — for baseball fans and non-fans alike. Start at 10am, then walk to Little Goat for lunch. The Chicago Cubs are owned by YPO member Tom Ricketts — see Partner Spotlight below.
Christkindlmarket at Gallagher Way ✦ Bonus
3610 N Clark St · FREE · Daily through Dec 31
German-style market set against the Wrigley Field marquee — one of the most uniquely Chicago holiday experiences available. 25+ vendors, Glühwein in signature collectible mugs, hand-crafted gifts, roasted nuts, bratwurst, and an outdoor ice skating rink. Walk straight out of Brickhouse Tavern.
December note: Southport storefronts go all-out on holiday window displays. Wrigley Field is lit all December. Flow: 10am Wrigley Tour (YPO-owned!) → 12pm Little Goat → 1:30pm Toons → 3pm Brickhouse → Christkindlmarket. Entire route is walkable.
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④
Old Town / Gold Coast
"Old Wells, New Energy & Christmas on the Magnificent Mile"
Culinary & Spirits Tour
1
11am — Lunch
The VIG Old Town
1527 N Wells St · Opens 11am
4.7★ neighborhood restaurant and bar. Moroccan turkey burger, lobster deviled eggs, the steak sandwich. Strong cocktails, bar TVs, and a crowd that's been coming for years. The best Wells Street lunch.
🍽 Lunch📺 TVs
2
1:30pm
The Rabbit Hole
1208 N Wells St
Old Town neighborhood bar with "a ton of TVs" per every regular who reviews it. Solid craft beer, Jenga at every table, a genuinely local crowd. Walk south on Wells — the best pure game-watching stop across all four routes.
📺 Best game-watching
3
3pm
LUXBAR
18 E Bellevue Pl, Gold Coast
Upscale Gold Coast bar/restaurant, 4.5★. Multiple TVs, outstanding burgers, sophisticated crowd. The perfect transition stop from Old Town into the Gold Coast shopping district and Oak Street. Sets the tone.
📺 TVs⭐ Gold Coast
Shopping · two distinct districts
Wells Street, Old Town
Independent boutiques, home goods, and gift shops between North Ave and Division. Walkable and genuinely local.
Oak Street, Gold Coast
Chicago's luxury corridor. Hermès, Chanel, St. John Knits, Intermix, Prada. Two concentrated blocks between Michigan and Rush.
Michigan Ave · Magnificent Mile
Holiday window displays, city lights, and department stores. December on the Mag Mile is iconic Chicago. Nordstrom, Bloomingdale's, Water Tower Place.
Activities
Featured activity
Kings Dining & Entertainment
1500 N Clybourn Ave, Old Town / Lincoln Park
Bowling, duckpin bowling, bocce ball, and an arcade all under one roof with a full bar, food menu, and sports TVs. A natural extension of the Wells Street bar route — competitive, social, and perfect for a mixed group. The entertainment continues well past the third drink.
Museum of Contemporary Art ✦ Bonus
220 E Chicago Ave · $22 · Open Sat 10am–5pm · 5-min walk from LUXBAR
A five-minute walk from LUXBAR. One of the better contemporary art museums in the country — 4.4★, 6,500+ reviews. Immersive exhibits, engaging curation. Trade bowling shoes for gallery floors if the group wants a refined close to the afternoon.
December note: Michigan Ave and Oak Street are at their absolute best in December — city-funded light installations and department store window displays. Christkindlmarket at Daley Plaza runs through Dec 24 — a short Uber from Gold Coast for mulled wine and strudel.
★ Partner Spotlight ★
YPO Member Spotlight
Lettuce Entertain You
Lettuce Entertain You Restaurants · Founded 1971, Chicago
★
R.J. Melman · YPO Chicago Chapter · Executive Committee Member · Chapter Chair 2020–2021
Founded1971 by Richard Melman & Jerry Orzoff in Chicago
Scale100+ restaurants · 60+ unique concepts nationwide
StructurePrivately held, family-owned
MarketsIL, FL, MD, MN, NV, TX, VA, DC — and expanding
Lincoln Park stops on today's route
Café Ba-Ba-Reeba — 2024 N Halsted St (tapas, since 1982)
R.J. Grunts — 2056 N Lincoln Ave (the very first Lettuce restaurant, 1971)
Summer House Santa Monica — 1954 N Halsted St (California-casual)
R.J. Melman joined Lettuce full time in 2001, was named President in 2017, and became CEO in January 2025 — succeeding Kevin Brown. His father Richard Melman, the company founder, said of the promotion: "When I look at R.J., it solidifies my belief in Lettuce's future."
Throughout his tenure R.J. and his partners have opened more than 25 of Lettuce's most notable concepts, including RPM Italian, RPM Steak, Aba, Sushi-san, Summer House, Three Dots and a Dash, and Bub City. Under his leadership Lettuce has expanded to Austin, Miami, Orlando, Nashville, and Dallas.
In 2023 R.J. was selected as one of EY's Entrepreneur of the Year® National winners. He and his partners also founded the Windy City Smokeout, Chicago's award-winning country music and BBQ festival. He resides in Chicago with his wife Kate and their two children.
YPO Member Spotlight
Chicago Cubs
Major League Baseball · Founded 1876 · Wrigley Field
★
Tom Ricketts · YPO Member · Chicago Chapter
AcquiredOctober 2009 by the Ricketts family · ~$900M transaction
HomeWrigley Field, 1060 W Addison St · Built 1914
Trophy2016 World Series Champions — ending a 108-year drought
EntitiesWrigley Field · Marquee Network · Marquee Development · Marquee Ventures
On today's Wrigleyville route
Wrigley Field Ballpark Tour — dugout, ivy, press box (10am)
Christkindlmarket at Gallagher Way — walk from the park (free)
Named SBJ & Baseball America Organization of the Year 2016
Tom Ricketts led his family's acquisition of the Chicago Cubs in 2009 in a ~$900 million transaction from the Tribune Company. When introduced as Chairman he outlined three goals: win the World Series, preserve and improve Wrigley Field for future generations, and be a good neighbor to Chicago's North Side. All three have been accomplished.
The Cubs won the 2016 World Series, ending a 108-year championship drought. Tom oversaw a landmark renovation of Wrigley Field, one of the most celebrated ballpark projects in MLB history. He was named Sports Business Journal Executive of the Year in 2017.
Beyond baseball, Tom is Chairman of InspereX. He holds an AB and MBA from the University of Chicago — where he spent his college years in the Wrigley Field bleachers. He and his wife Cecelia (they met at Wrigley Field) live in the Chicago area with their five children.