Chicago, Illinois

The Windy City: A Traveler’s Guide to Chicago

Chicago, the third-largest city in the United States, is a world-class destination that offers something for everyone. From its striking lakefront architecture to its deep cultural heritage, there is no shortage of things to see, eat, and do in this remarkable midwestern city.

Where to Visit

  • Millennium Park: Opened in 2004 on the former site of rail yards, Millennium Park has become one of the most visited public spaces in the country. The centerpiece is Anish Kapoor’s “Cloud Gate” sculpture, popularly called “The Bean,” a 110-ton reflective steel structure that warps and mirrors the surrounding skyline. Nearby, the Crown Fountain features two 50-foot glass block towers that project video images of Chicago residents. The Jay Pritzker Pavilion, designed by Frank Gehry, hosts free outdoor concerts throughout summer and is home to the Grant Park Music Festival. The park connects directly to the lakefront and the Art Institute, making it a natural starting point for a day in the Loop.

  • Willis Tower (formerly Sears Tower): Completed in 1973, the Willis Tower held the title of world’s tallest building for over two decades. The Skydeck on the 103rd floor sits at 1,353 feet and offers unobstructed views stretching into Indiana, Michigan, and Wisconsin on clear days. The Ledge, a set of glass-floored balconies that extend four feet beyond the building’s facade, lets visitors look straight down to the street below. Tickets can be purchased in advance online to avoid long lobby queues, particularly on weekends and during summer.

  • The Art Institute of Chicago: One of the largest and most visited art museums in the country, the Art Institute holds an encyclopedic collection spanning 5,000 years. Highlights include Georges Seurat’s “A Sunday on La Grande Jatte,” Grant Wood’s “American Gothic,” and an extensive collection of Impressionist works including paintings by Monet, Renoir, and Degas. The Modern Wing, added in 2009, significantly expanded the museum’s contemporary holdings. The museum is located directly adjacent to Millennium Park and is accessible via the iconic lion statues at its Michigan Avenue entrance.

  • Navy Pier: Stretching 3,300 feet into Lake Michigan, Navy Pier has served as a training facility, a university campus, and now a public entertainment destination. A large Ferris wheel offers views of the city and the lake. During summer, Chicago Shakespeare Theater performs on the pier and fireworks shows run on Wednesday and Saturday evenings.

  • The 606 Trail: This elevated rail trail runs 2.7 miles through the Bucktown, Wicker Park, Logan Square, and Humboldt Park neighborhoods. Built on a former rail line, it is comparable in concept to New York’s High Line and offers a ground-level view of Chicago’s residential neighborhoods away from downtown crowds.

  • The Chicago Riverwalk: The main branch of the Chicago River has been transformed into a pedestrian promenade with kayak rentals, outdoor dining, and architecture boat tours departing from multiple docks. The river was famously reversed in 1900 to protect the city’s drinking water supply, and on St. Patrick’s Day it is dyed green. River architecture tours are among the best ways to understand Chicago’s role as a center of American architectural innovation.

Where to Eat

  • Deep-dish pizza: Chicago’s deep-dish pizza is a distinct style with a thick buttery crust pressed up the sides of a round steel pan, topped with cheese, fillings, and a chunky tomato sauce layered on top. Lou Malnati’s has been making it since 1971 and uses a proprietary sausage blend. Pequod’s in Lincoln Park is known for its caramelized crust formed where cheese meets the edge of the pan. Giordano’s offers a stuffed variant with a second layer of dough beneath the sauce. A single deep-dish pie takes roughly 45 minutes to bake, so ordering promptly is advisable. The style is best understood as a casserole-like dish rather than a traditional pizza.

  • Chicago-style hot dogs: A Chicago dog is an all-beef frankfurter on a poppy seed bun topped with yellow mustard, chopped white onion, neon-green sweet pickle relish, a dill pickle spear, tomato slices, pickled sport peppers, and a dash of celery salt. Ketchup is conspicuously absent and is considered incorrect. Portillo’s, with multiple Chicago locations, is one of the most recognized spots for both hot dogs and Italian beef sandwiches. Vienna Beef is the dominant frank supplier across the city and has been since 1893.

  • Italian beef: The Italian beef sandwich is thinly sliced seasoned roast beef served on a long Italian roll that is often dipped in the meat’s cooking juices. It can be ordered “wet” (fully dunked), “dry,” or “dipped” on one side. Giardiniera, a spicy pickled vegetable relish, is a common topping. Portillo’s and Al’s Beef are longstanding spots for this Chicago original.

  • Girl & the Goat: Chef Stephanie Izard’s flagship restaurant in the West Loop focuses on shared plates with bold flavors and unexpected ingredient combinations. Reservations are strongly recommended.

  • Black Dog Gelato: This small gelato shop in Ukrainian Village produces small-batch flavors using locally sourced ingredients. The menu rotates seasonally and often includes savory or unconventional combinations.

Where to Stay

  • The Langham Chicago: Located in the River North neighborhood inside the former IBM Building, a landmark modernist tower designed by Mies van der Rohe, the Langham offers upscale accommodations with views of the river and the Loop.

  • The Four Seasons Hotel Chicago: Situated in the Gold Coast, the Four Seasons occupies the upper floors of a mixed-use tower steps from the Magnificent Mile. It is a consistently well-regarded option for service and amenities.

  • The Kimpton Hotel Allegro: A mid-priced boutique option in the Loop, the Allegro has a rooftop bar with city views and is walking distance from Millennium Park and the theater district.

  • Short-term rentals: For longer stays or groups, apartments in neighborhoods like Logan Square, Wicker Park, or Lincoln Square provide a more residential experience and are generally more affordable than downtown hotels.

Activities

  • Architecture boat tours: Chicago Architecture Center runs 90-minute river tours covering the history and design of over 50 buildings visible from the water. These tours are among the most efficient ways to understand the city’s architectural legacy, from the early skyscrapers of Louis Sullivan to the postwar towers of Mies van der Rohe.

  • Catch a Cubs game at Wrigley Field: Built in 1914, Wrigley Field is the second-oldest Major League Baseball stadium in use. The park retains its hand-operated scoreboard, ivy-covered outfield walls, and rooftop bleacher culture that has grown up on the surrounding buildings. Games sell out quickly during warm weather months.

  • Visit the Lincoln Park Zoo: This free zoo covers 35 acres along the lakefront and is open year-round. It holds over 1,100 animals and sits adjacent to Lincoln Park, the city’s largest public park, which has a conservatory, a lagoon, and access to the Lakefront Trail.

  • Walk the Lakefront Trail: This 18.5-mile paved path runs along the western shore of Lake Michigan from Edgewater in the north to South Shore in the south. Cyclists and runners share the path, and it passes through multiple neighborhoods and public beaches. North Avenue Beach and Oak Street Beach are among the most frequented during summer.

  • Explore Wicker Park and Bucktown: These adjacent northwest-side neighborhoods are known for independent record shops, used bookstores, live music venues, and a concentration of restaurants that skew toward smaller, chef-owned concepts.

  • Museum Campus: Three major institutions sit close together on the lakefront south of the Loop: the Field Museum of Natural History, the Shedd Aquarium, and the Adler Planetarium. A combination pass reduces the cost of visiting multiple sites.

Tips

  • Weather: Chicago weather shifts rapidly. Summer temperatures can reach the 90s Fahrenheit with high humidity, while winters bring lake-effect wind that drops effective temperatures well below freezing. Spring and fall are comfortable but unpredictable. Layering is useful in any season.

  • Public transit: The CTA ‘L’ train connects O’Hare and Midway airports to downtown and runs to most major neighborhoods. Single-ride cards and rechargeable Ventra cards are available at station kiosks. A 24-hour or 3-day pass is cost-effective for visitors planning multiple daily trips.

  • Neighborhoods: Chicago’s 77 officially designated community areas each have a distinct character. Pilsen has a strong Mexican American cultural identity and is home to the National Museum of Mexican Art. Chinatown along Wentworth Avenue has been a city fixture since the 1910s. The South Side’s Bronzeville neighborhood has significant ties to the Great Migration and the development of Chicago blues and gospel music.

  • Crowds and reservations: Popular restaurants fill weeks in advance. Booking ahead is advisable for anything beyond casual dining. Museum crowds peak on weekend mornings; arriving at opening time or later in the afternoon reduces wait times.

Other Things to Consider

  • Safety: Awareness of surroundings is advisable as in any large city. Most tourist areas including the Loop, Grant Park, the Magnificent Mile, and Lincoln Park are generally busy and well-trafficked.

  • Accessibility: The CTA and most major attractions have made accessibility improvements, though some older elevated stations and historic buildings have limitations. Checking specific venue websites before visiting is worthwhile.

  • Sustainability: Chicago’s public transit system reduces the need for rental cars in most situations. Many hotels participate in energy and recycling programs, and the city has an active green building certification program rooted in its architectural culture.

Chicago rewards extended exploration. The neighborhoods beyond downtown each carry distinct histories and offer food, music, and architecture that are harder to find in the concentrated tourist corridor along the lakefront.