Words: Elaine Glusac
Illustrations: Michael Driver
The best of Chicago — from modern art and architecture to lakeside parks and restaurants made famous on the streaming series The Bear — rounds out this perfect two-day guide to the Windy City.
Day One
10 a.m.
The Impressionism collection alone could consume hours at the Art Institute of Chicago. But after paying homage to Monet, seek out the quirkier corners of the encyclopedic museum, including the Thorne Miniature Rooms devoted to meticulous architectural models from Gothic to modern styles in dollhouse proportions.
12 p.m.
Join the throngs in snapping funhouse selfies and cityscapes in the mirrored surface of Cloud Gate, the kidney-bean-shaped icon of Millennium Park popularly known as “The Bean.” Sculptor Anish Kapoor’s crowd favorite is newly accessible after a renovation of the plaza supporting the 110-ton landmark.
1 p.m.
Chicago’s beloved Italian beef sandwiches shot to stardom with the Emmy-winning TV series The Bear — poised for a season 5 drop this summer — modeled on River North’s humble sandwich shop Mr. Beef. Fans line up for the two-fisted shaved beef subs topped with sweet or hot peppers. Order one dry, wet or dipped for varying amounts of cooking juice — and a delicious mess.
3 p.m.
Work off lunch along Chicago’s 18-mile Lakefront Trail. The paved path follows the Lake Michigan shore, stringing together lively beaches, parks and attractions like the Lincoln Park Zoo, set against the backdrop of the city’s stunning skyline. Rental bikes are readily available through the city’s Divvy shared bike system.
7 p.m.
Gussy up for a meal that’s a feast for both the eyes and the appetite at Ever. Chef Curtis Duffy’s creative two-Michelin-starred spot plays the world’s best restaurant in The Bear and, in real life, serves eight- to 10-course tasting menus. Its sibling cocktail lounge After invites lingering post-dessert.
Day Two
9 a.m.
Caffeinate in style at the street-art-filled Sawada Coffee in the restaurant-centric West Loop. Founded in partnership with the famed Japanese latte artist Hiroshi Sawada, the industrial-chic coffee shop specializes in east-meets-west matcha lattes alongside treats like buttermilk donuts and rainbow sprinkle cookies.
10 a.m.
Among Chicago’s 77 official neighborhoods, take a trip south to historic Hyde Park, home to the Griffin Museum of Science and Industry — originally constructed for the 1893 World’s Fair — the neo-Gothic campus of the University of Chicago and the Prairie School architecture of Frank Lloyd Wright. Tour Wright’s campus-adjacent Robie House with signature leaded-glass windows and cantilevered eaves (the tour is included with the Go City Pass/Card available to HGVClub Members).
12 p.m.
President Barack Obama got his political start here and dined so often at Hyde Park’s 1921-vintage restaurant Valois that the menu includes a list of his favorite foods. Convivial and delicious, the old-school cafeteria has a strong following for substantial daily specials like baked chicken, macaroni and cheese and hamburger steak with onions.
2 p.m.
Valois anchors the east end of 53rd Street, the neighborhood’s bustling retail district, where you can peruse bins full of vinyl at Hyde Park Records. Along the way don’t miss the Silver Room for gifts, accessories and community events like tango lessons, and Suuri Design for jewelry and locally made body care products.
7 p.m.
You can’t leave Chicago without sampling its marquee culinary invention: deep-dish pizza. Pizzeria Uno and Lou Malnati’s squabble over who first created the inches-high pie loaded with cheese, but locals love Pequod’s Pizza for its caramelized crusts, as proven by its season 2 cameo in, of course, The Bear.
7 p.m.
Cap off your weekend with fine French cuisine at Le Yaca, where dishes like pan-seared Dover sole and poached lobster tails are paired with white linens and attentive service for a memorable finale to your trip.
4 p.m.
After an action-packed afternoon, unwind with a glass of Virginia’s finest at a nearby winery like the Williamsburg Winery or Saudé Creek. The area’s wine scene is booming, thanks to the region’s unique climate and rich soil. Many wineries offer barrel room tours, tastings with scenic views and indoor lounges. Spring visitors may also catch the first blooms in vineyard gardens.
2 p.m.
Wander through Busch Gardens Williamsburg to see charming European-style villages, enjoy live shows and experience everything from high-speed coasters to gentler attractions perfect for younger visitors. The park opens on select weekends in January, and on all weekends throughout February and March. Check the park’s calendar for current hours and special event details before you visit.
12 P.M.
Swing by Shorty’s Diner for a laid-back lunch of hearty American favorites, including burgers, milkshakes and all-day breakfast served in a cheerful, retro setting.
Day two
9 A.M.
Just a short drive from downtown Williamsburg, Jamestown Settlement explores the story of America’s first permanent English colony. Interactive indoor galleries and outdoor recreations, including a Powhatan village and replicas of the 1607 ships, bring history to life.
8 P.M.
As the sun sets, embark on one of Williamsburg’s famous ghost tours. A spirited guide will lead you through cobblestoned streets and shadowy alleys to reveal haunted houses, eerie legends and real-life colonial mysteries. Afterward, enjoy a late supper at Downstairs at Fat Canary, a relaxed wine bar offering shareable small plates.
3 P.M.
Built in the 1920s as one of the first planned shopping districts in the United States, Merchants Square blends colonial flair with modern boutique charm. Spend some time browsing the bookstores, grabbing warm cider and picking up locally made wares. Stop by Wythe Candy to satisfy a sweet tooth with gourmet fudge, candy apples or a unique gift to take home.
1:30 P.M.
Steps from the main thoroughfare, settle in for a colonial-style meal at King’s Arms Tavern. The historic dining room offers period dishes like peanut soup and hearty stews, served by staff in 18th-century attire. Candlelight and fireplaces add a cozy winter warmth.
12 p.m.
Hear powerful stories on the African American History walking tour that winds through the historic district. This powerful and insightful experience is the city’s only tour dedicated solely to Black history.
Day one
9 a.m.
Start your day with a deep dive into the 18th century at Colonial Williamsburg, America’s largest living history museum. Spread across 300 acres, interactive storytelling brings the Revolutionary era to life through musket demonstrations and historic court reenactments. Visit artisan workshops to watch traditional crafts in action — or try your hand at one.
7 p.m.
You can’t leave Chicago without sampling its marquee culinary invention: deep-dish pizza. Pizzeria Uno and Lou Malnati’s squabble over who first created the inches-high pie loaded with cheese, but locals love Pequod’s Pizza for its caramelized crusts, as proven by its season 2 cameo in, of course, The Bear.
2 p.m.
Valois anchors the east end of 53rd Street, the neighborhood’s bustling retail district, where you can peruse bins full of vinyl at Hyde Park Records. Along the way don’t miss the Silver Room for gifts, accessories and community events like tango lessons, and Suuri Design for jewelry and locally made body care products.
12 p.m.
President Barack Obama got his political start here and dined so often at Hyde Park’s 1921-vintage restaurant Valois that the menu includes a list of his favorite foods. Convivial and delicious, the old-school cafeteria has a strong following for substantial daily specials like baked chicken, macaroni and cheese and hamburger steak with onions.
10 A.m.
Among Chicago’s 77 official neighborhoods, take a trip south to historic Hyde Park, home to the Griffin Museum of Science and Industry — originally constructed for the 1893 World’s Fair — the neo-Gothic campus of the University of Chicago and the Prairie School architecture of Frank Lloyd Wright. Tour Wright’s campus-adjacent Robie House with signature leaded-glass windows and cantilevered eaves (the tour is included with the Go City Pass/Card available to HGVClub Members).
Day two
9 a.m.
Caffeinate in style at the street-art-filled Sawada Coffee in the restaurant-centric West Loop. Founded in partnership with the famed Japanese latte artist Hiroshi Sawada, the industrial-chic coffee shop specializes in east-meets-west matcha lattes alongside treats like buttermilk donuts and rainbow sprinkle cookies.
7 p.m.
Gussy up for a meal that’s a feast for both the eyes and the appetite at Ever. Chef Curtis Duffy’s creative two-Michelin-starred spot plays the world’s best restaurant in The Bear and, in real life, serves eight- to 10-course tasting menus. Its sibling cocktail lounge After invites lingering post-dessert.
3 p.m.
Work off lunch along Chicago’s 18-mile Lakefront Trail. The paved path follows the Lake Michigan shore, stringing together lively beaches, parks and attractions like the Lincoln Park Zoo, set against the backdrop of the city’s stunning skyline. Rental bikes are readily available through the city’s Divvy shared bike system.
1 p.m.
Chicago’s beloved Italian beef sandwiches shot to stardom with the Emmy-winning TV series The Bear — poised for a season 5 drop this summer — modeled on River North’s humble sandwich shop Mr. Beef. Fans line up for the two-fisted shaved beef subs topped with sweet or hot peppers. Order one dry, wet or dipped for varying amounts of cooking juice — and a delicious mess.
12 p.m.
Join the throngs in snapping funhouse selfies and cityscapes in the mirrored surface of Cloud Gate, the kidney-bean-shaped icon of Millennium Park popularly known as “The Bean.” Sculptor Anish Kapoor’s crowd favorite is newly accessible after a renovation of the plaza supporting the 110-ton landmark.
Day one
10 a.m.
The Impressionism collection alone could consume hours at the Art Institute of Chicago. But after paying homage to Monet, seek out the quirkier corners of the encyclopedic museum, including the Thorne Miniature Rooms devoted to meticulous architectural models from Gothic to modern styles in dollhouse proportions.
Words: Fiona Tapp
Illustrations: Michael Driver
From colonial towns and candlelit taverns to thrilling theme parks and local distilleries, this two-day guide to Williamsburg, Virginia, blends rich history with modern experiences
From colonial towns and candlelit taverns to thrilling theme parks and local distilleries, this two-day guide to Williamsburg, Virginia, blends rich history with modern experiences
Day one
9 a.m.
Start your day with a deep dive into the 18th century at Colonial Williamsburg, America’s largest living history museum. Spread across 300 acres, interactive storytelling brings the Revolutionary era to life through musket demonstrations and historic court reenactments. Visit artisan workshops to watch traditional crafts in action — or try your hand at one.
12 p.m.
Hear powerful stories on the African American History walking tour that winds through the historic district. This powerful and insightful experience is the city’s only tour dedicated solely to Black History.
1:30 P.M.
Steps from the main thoroughfare, settle in for a colonial-style meal at King’s Arms Tavern. The historic dining room offers period dishes like peanut soup and hearty stews, served by staff in 18th-century attire. Candlelight and fireplaces add a cozy winter warmth.
3 P.M.
Built in the 1920s as one of the first planned shopping districts in the United States, Merchants Square blends colonial flair with modern boutique charm. Spend some time browsing the bookstores, grabbing warm cider and picking up locally made wares. Stop by Wythe Candy to satisfy a sweet tooth with gourmet fudge, candy apples or a unique gift to take home.
8 P.M.
As the sun sets, embark on one of Williamsburg’s famous ghost tours. A spirited guide will lead you through cobblestoned streets and shadowy alleys to reveal haunted houses, eerie legends and real-life colonial mysteries. Afterward, enjoy a late supper at Downstairs at Fat Canary, a relaxed wine bar offering shareable small plates.
Day two
9 A.M.
Just a short drive from downtown Williamsburg, Jamestown Settlement explores the story of America’s first permanent English colony. Interactive indoor galleries and outdoor recreations, including a Powhatan village and replicas of the 1607 ships, bring history to life.
12 P.M.
Warm up with a guided tasting at 8 Shires, a unique distillery specializing in colonial-era spirits. Sample whiskey made using 18th-century recipes to try a small-batch gin — every sip tells a story. Swing by Shorty’s Diner for a laid-back lunch of hearty American favorites, including burgers, milkshakes and all-day breakfast served in a cheerful, retro setting.
2 p.m.
Wander through Busch Gardens Williamsburg to see charming European-style villages, enjoy live shows and experience everything from high-speed coasters to gentler attractions perfect for younger visitors. The park opens on select weekends in January, and on all weekends throughout February and March. Check the park’s calendar for current hours and special event details before you visit.
4 p.m.
After an action-packed afternoon, unwind with a glass of Virginia’s finest at a nearby winery like the Williamsburg Winery or Saudé Creek. The area’s wine scene is booming, thanks to the region’s unique climate and rich soil. Many wineries offer barrel room tours, tastings with scenic views and indoor lounges. Spring visitors may also catch the first blooms in vineyard gardens.
7 p.m.
Cap off your weekend with fine French cuisine at Le Yaca, where dishes like pan-seared Dover sole and poached lobster tails are paired with white linens and attentive service for a memorable finale to your trip.
Words: Fiona Tapp
Illustrations: Michael Driver
Where to Stay
Tucked among towering trees, The Historic Powhatan, a Hilton Vacation Club has 1- to 4-Bedroom Suites with full kitchens, indoor and outdoor pools, mini-golf, tennis courts and a historic manor house. For a family-friendly base near Busch Gardens, try Parkside Williamsburg Resort. It offers spacious Villas with full kitchens, washers and dryers, fireplaces and balconies, making it ideal for groups or longer stays.
The Historic Powhatan, a Hilton Vacation Club brings history to life on a trip to Williamsburg
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