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.
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 4 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.
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: 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
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.
Words: Elaine Glusac
Illustrations: Michael Driver
Where to Stay
Located on downtown Michigan Avenue, Chicago Magnificent Mile, a Hilton Grand Vacations Club puts Guests in the center of city life with attractions like Navy Pier and Lake Michigan just blocks away. Take time to admire the views from the fifth-floor outdoor pool deck or refuel over flatbreads and Illinois-made craft beers at the casual HotHouse cafe. Also on the east side of the city near Grant Park is Hotel Blake which also has stunning city views. Make use of the business center or state-of the-art gym, or just kick back and relax in stylish Suites that include sofas, wet bars and mini-fridges for downtime done right.
Chicago Magnificent Mile, a Hilton Grand Vacations Club is at the heart of the city
Plan your trip to Chicago today.
Visit bluegreenowner.com or club.hiltongrandvacations.com to book now!
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