Chicago Illinois Architecture Cruises and Deep-Dish Pizza

Why visit Chicago

Few American cities combine big-city culture with such easy access to open space. Chicago's founders protected much of the lakefront as public land, so a continuous trail of roughly eighteen miles runs past beaches, harbors and parks with the skyline as a backdrop.

The city is also a serious food and music town. Deep-dish pizza, Italian beef and the dragged-through-the-garden hot dog are local institutions, but so are the taquerias of Pilsen and Little Village, the bakeries of Chinatown and the chef-driven restaurants of the West Loop.

Downtown icons: the Loop, the lakefront and the river

Millennium Park and Cloud Gate

Millennium Park is the city's front yard, a former rail yard turned into gardens, sculpture and performance space. Its star is Cloud Gate, the polished steel sculpture locals call the Bean, which reflects the skyline and anyone standing beneath it.

Art Institute of Chicago

Just south of the park, the Art Institute holds one of the great encyclopedic collections in the world. Highlights include Grant Wood's American Gothic, Edward Hopper's Nighthawks, Georges Seurat's A Sunday on La Grande Jatte and a deep collection of Impressionist paintings, plus the Thorne Miniature Rooms, which delight even reluctant museumgoers.

Chicago River and the architecture cruise

If you do only one tour in Chicago, make it an architecture cruise on the river. Narrated trips run by the Chicago Architecture Center with its cruise partner, and by several other operators, glide along the main stem and branches of the river past the Wrigley Building, Marina City's corncob towers, the Merchandise Mart and many more.

Chicago Cultural Center

Across Michigan Avenue from Millennium Park, the Chicago Cultural Center was the city's first central library. Step inside to see the Tiffany glass dome in Preston Bradley Hall, considered one of the largest of its kind, along with free exhibitions and concerts. Thirty to forty-five minutes is enough.

Museum Campus, skyline views and Navy Pier

Field Museum

The Field Museum anchors Museum Campus on the lakefront south of Grant Park. SUE, one of the largest and most complete Tyrannosaurus rex skeletons ever found, has its own gallery, while Maximo the titanosaur fills the main hall.

Willis Tower Skydeck

For a bird's-eye view, ride to the Skydeck on the 103rd floor of Willis Tower, long the tallest building in the Western Hemisphere. The glass boxes of the Ledge jut out from the building so you can look straight down.

Navy Pier

Navy Pier stretches more than half a mile into Lake Michigan and mixes family attractions with boat departures. Ride the Centennial Wheel, walk out to the end of the pier for skyline views, and check the summer schedule for fireworks. Two to three hours is plenty.

Neighborhoods, ballparks and the South Side

Wrigley Field and Wrigleyville

Opened in 1914, Wrigley Field is famous for its ivy-covered outfield walls, hand-turned scoreboard and red marquee. Catching a Cubs game during the season is a classic Chicago afternoon, and stadium tours run on many non-game days.

Lincoln Park and the zoo

North of downtown, Lincoln Park is the city's largest park, with lagoons, beaches, a conservatory and the Lincoln Park Zoo, one of the oldest zoos in the country and free to enter. Combine it with a walk to North Avenue Beach for one of the best skyline views in the city.

Griffin Museum of Science and Industry

In Hyde Park, the Museum of Science and Industry, now named the Griffin Museum of Science and Industry, fills the only major building surviving from the 1893 World's Columbian Exposition.

Pilsen and the 606

Pilsen, on the Lower West Side, is known for its colorful murals and Mexican heritage. The National Museum of Mexican Art, free to visit, holds an excellent collection, and 18th Street is lined with bakeries and taquerias.

Food and local flavors

Chicago's food reputation goes far beyond pizza, but deep-dish is a fine place to start.

For broader eating, head to the West Loop's Randolph Street and Fulton Market for chef-driven restaurants, Pilsen and Little Village for Mexican food, Chinatown for dim sum and bakeries, Devon Avenue for South Asian cooking, and Andersonville for Swedish heritage and neighborhood cafes.

Where to stay

The Loop puts you within walking distance of Millennium Park, the Art Institute and the river, with every L line nearby. It suits first-time visitors and short trips, though it quietens in the evenings.

For a more local feel, consider the West Loop, ideal if eating well is your priority, or Lincoln Park and Lakeview, which put you near the park, the zoo and Wrigley Field with easy Red and Brown Line access. Wicker Park and Logan Square appeal to travelers who like independent shops, bars and music venues and do not mind a train ride downtown.

Best time to visit

Summer, from June through August, is Chicago at its liveliest.

Winters are cold and windy, with snow and wind chills well below freezing, but the city stays busy. Holiday lights along Michigan Avenue and the Christkindlmarket bring festive cheer from late November through December, and indoor museums are less crowded in January and February.

Getting there and getting around

Chicago has two major airports. O'Hare International, northwest of the city, is one of the busiest airports in the country and is linked to downtown by the CTA Blue Line, which runs around the clock.

Within the city, the CTA's elevated and subway trains, known as the L, and its bus network reach nearly every sight in this guide.

A suggested itinerary

First day

Start at Millennium Park and Cloud Gate early, then spend the late morning and early afternoon at the Art Institute.

Second day

Head to Museum Campus for the Field Museum, then walk along the lakefront toward the skyline.

Third day

Take the train north to Lincoln Park for the zoo and North Avenue Beach, then continue to Wrigleyville for a game or a stadium tour.

Fourth day

If you have an extra day, spend the morning in Hyde Park at the Griffin Museum of Science and Industry and Robie House, then lunch in Pilsen and finish with a walk on the 606 before dinner in Logan Square.

Practical tips

• Book architecture cruises, Cubs tickets and popular restaurants in advance during summer and on festival weekends.
• Check the official websites for current hours and fees; several museums offer free days for Illinois residents only, so confirm before planning around them.
• Layers are essential in every season, since lake breezes can drop the temperature quickly near the water.
• Use the L instead of driving downtown, and tap a contactless card or phone to pay fares.
• Swim only at guarded beaches during posted hours, and heed flags and warnings about waves and rip currents on Lake Michigan.
• Stay aware of your surroundings at night, as in any large city, and stick to busy, well-lit streets and stations.

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