Rebecca Holland - Moon Chicago

REBECCA HOLLAND

Chicago is a thriving, multicultural hub seated on vast Lake Michigan. Fed by the lake, the Chicago River snakes its way through downtown, winding past the soaring architecture of the Loop, slicing across Michigan Avenues Magnificent Mile, and cruising along a fusion of skyline sights, impressive museums, and verdant parks and gardens.

In summer, Chicagoans embrace the seasonal warmth by flocking to the lake with sailboats, personal watercraft, and paddleboards. Sunbathers line North Avenue Beach, while the city explodes with street festivals, food fairs, rooftop clubs, and outdoor activities.

Winter holds a certain magic, too. The lake turns icy blue with frozen blocks drifting as far as the eye can see. Crackling frost decorates Cloud Gate and drapes the skyline. Chicagoans, bundled in wool jackets and scarves, feel a sense of pridenothing can stop them from enjoying their city. Youll find them ice-skating at Millennium Park, browsing a bustling Christmas market, packed into comedy clubs and music halls, or sipping a warm cocktail by the fire at a local lounge.

What Chicagoans love most about their city are its colorful neighborhoods, each with its own distinct heritage and character. West Side has the best tacos and the coolest street art. Lincoln Parks boutiques cant be beat. Hyde Park is home to a history and culture so rich it could fill its own book. Each neighborhood is a microcosm of art, culture, and, of course, food, and its residents love it so much its palpable.

Mostly though, what makes this city special are the people. Chicago is a big city with small-town charm, built by working-class immigrants and filled with folks who say hi to each other on the street. The heart of the Midwest has a lot of heart. Visitors are sure to fall in love.

sunset boat cruises at Navy Pier ()

1928 bas-relief sculptures along the Chicago River ()

Wrigley Field ()

Chicago Theatre ()

Cloud Gate at Millennium Park ()

Chicago skyline from North Avenue Beach ()

The Art Institute of Chicago: One of the countrys oldest and largest art museums houses more than 300,000 works and 30 rotating special exhibitions (

Millennium Park: World-class architecture, public art, and landscape design come together in this 25-acre park that serves as a hub for Chicagos cultural programs and outdoor activities ().

Willis Tower Skydeck: At 110 stories, the Willis Tower is the second-tallest building in North America. Enjoy 360-degree skyline views from the beautiful glass-bottom Skydeck ().

Navy Pier: Its wealth of attractions include the 196-foot-tall Centennial Wheel, one of Chicagos biggest draws ().

Wrigley Field: This historic stadium brings in locals and tourists game after game. Whether the Cubs win or lose, its always a good time ().

Shedd Aquarium: The largest indoor aquarium in the world is home to more than 32,000 animals and 1,500 species and features a range of exhibits on everything from local waters to the Amazon ().

Chicago Architecture River Cruise: Buildings tell the story of how Chicago grew from a small town to a thriving city. The best way to see them is on this scenic river cruise ().

Lakefront Trail: These 18 miles pass skyline views, nature sanctuaries, boat harbors, and boardwalks ().

Second City: The legendary improvisational comedy club where many of Saturday Night Lives stars got their start turns out hilarious revues every night ().

Chicagos Historic Jazz Clubs: Chicago played a leading role in the evolution of jazz in the early 1900s. Today, jazz clubs are still a vital part of the citys diversity, bringing in acts from around the city and the world ().

THE BEST OF CHICAGO

This three-day itinerary covers the best the city has to offerfrom must-see sights to neighborhood favorites. Spend the first day downtown, then explore some of the northern neighborhoods on the second day before finishing up with the Museum Campus on the third day. Plan to stay in a hotel in the Loop or Near North for the easiest access to public transportation.