Cheap flights to Chicago

Quick summary

The city that invented the skyscraper

Third-largest city in the US, and its architectural laboratory

Chicago counts roughly 2.7 million residents within city limits and close to 9.9 million across its metro area, making it the third-largest city in the United States and the economic anchor of the Midwest, home to more than 400 corporate headquarters, 31 of them Fortune 500 companies. What sets it apart from the outset, though, is what happened after the Great Chicago Fire tore through the city on October 8, 1871: stricter building codes pushed architects toward steel and masonry instead of wood, and in 1885 the Home Insurance Building went up downtown — widely credited as the first skyscraper built on a metal frame. Chicago has been treated as the world's open-air textbook of vertical architecture ever since.

The Loop, financial core and open-air museum

Named after the loop the elevated train tracks trace around it, the Loop packs in the city's tallest towers, the Chicago Board of Trade and the Art Institute of Chicago — founded in 1879 during the reconstruction years and settled since 1893 into its Michigan Avenue building, guarded by its famous bronze lions.

Not to be missed

Millennium Park and the Bean

Opened in 2004, Millennium Park has become one of the most visited public spaces in the country. Its centerpiece is Cloud Gate — nicknamed "The Bean" for its shape — a 20-meter-long, 10-meter-high sculpture by Anish Kapoor made of 168 polished stainless steel plates fused into a single seamless, mirror-like surface that bends the skyline back at anyone standing beneath it. The park also holds Frank Gehry's Jay Pritzker Pavilion, an open-air concert venue whose ribboned steel bandshell is a landmark in its own right.

Views

The Willis Tower Skydeck, 412 meters above the street

Completed in 1973 as the Sears Tower, the Willis Tower rises 442 meters over 110 floors and held the title of world's tallest building for nearly 25 years. The Skydeck, on floor 103, is the highest observation deck in the country at roughly 412 meters above ground, and its glass-floored balconies — The Ledge — jut out more than a meter over open air for a straight-down view of the street below.

To discover

Museum Campus and the lakefront

Field Museum, Shedd Aquarium, Adler Planetarium

Three major institutions sit within walking distance of each other on roughly 23 hectares of lakefront parkland. The Field Museum's most famous resident is SUE, the most complete Tyrannosaurus rex skeleton ever found. The Shedd Aquarium, one of the first large indoor aquariums in the world when it opened in 1930, is now home to more than 32,000 aquatic animals, including belugas in an Oceanarium built to mirror the Pacific Northwest coast. Next door, the Adler Planetarium — the first planetarium in the Western Hemisphere, also from 1930 — pairs dome shows with one of the best free skyline views in the city, from the sloped lawn just outside.

42 kilometers of shoreline

Chicago stretches for close to 42 kilometers along Lake Michigan, with public beaches and the Lakefront Trail running the length of it — a direct, uninterrupted relationship with open freshwater that few American cities of this size can match. Navy Pier, a nearly one-kilometer-long pier opened in 1916, adds a Ferris wheel, a children's museum and lake and river cruises to the mix, while the Riverwalk downtown strings together cafés and boarding docks for the architecture cruises that count among the city's best-reviewed tours.

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Getting around and budget

The Blue Line, and what things cost

O'Hare sits about 27 km northwest of downtown, and the "L" train's Blue Line is the simplest, cheapest way to cover that distance — roughly 40 minutes to the Loop, running 24 hours a day, a service only a handful of cities worldwide offer on a local rail line. A taxi or rideshare covers the same route in 30 to 45 minutes depending on traffic on the Kennedy or Eisenhower expressways, for something closer to $45-70. Once downtown, the Loop's colored lines (Red, Brown, Green) cover the main tourist neighborhoods without a car. On budget, Chicago runs mid-pack for a major US city: two-star hotels average roughly $85-110 a night outside peak season, with hostel beds starting under $55, though it's worth knowing the city layers a steep 17.4% hotel tax plus a flat destination fee onto quoted room rates — worth budgeting for before you book.

Shopping

The Magnificent Mile

This 13-block stretch of Michigan Avenue, between the Chicago River and Oak Street, lines up more than 450 stores — department stores like Bloomingdale's, Nordstrom and Neiman Marcus alongside luxury boutiques, all against a backdrop of skyscrapers and lake views. The nickname dates to the 1940s, when the corridor emerged as Chicago's retail spine in the years after the Great Depression. Water Tower Place and The Shops at North Bridge are its two big vertical malls.

Neighborhoods

Beyond the Loop

Wicker Park

A former working-class district turned one of the city's trendiest pockets, with vintage shops, record stores, independent breweries and a strong local music scene.

Hyde Park

South of downtown, this university neighborhood is home to the University of Chicago and the Museum of Science and Industry, housed in one of the last surviving buildings from the 1893 World's Columbian Exposition.

Pilsen and Chinatown

Pilsen, historically Mexican, is known for its street murals and Latin American food scene, anchored by the National Museum of Mexican Art. South of the Loop, one of the country's oldest Chinatowns organizes itself around Wentworth Avenue, marked by its red-and-gold ceremonial gate, traditional bakeries and dim sum restaurants — an easy detour by train from downtown.

Sport & music

Wrigley Field and the sound of Chicago blues

Built in 1914 and home to the Cubs since 1916, Wrigley Field is the second-oldest ballpark still in use in Major League Baseball, nicknamed the "Friendly Confines." Its ivy-covered outfield walls and hand-turned scoreboard, in continuous use since the 1930s, make it one of the most recognizable stadiums in American sport — it was also the last MLB park to install lights, in 1988. The surrounding Wrigleyville neighborhood fills with bars on game nights. Musically, Chicago is where Delta blues plugged in and went electric in the 1940s and '50s, through artists like Muddy Waters and Howlin' Wolf; historic clubs on the South Side and near the Loop keep that live tradition going most nights of the week, a very different way to hear the city than its downtown attractions.

Food

Deep-dish pizza and the Chicago dog

Chicago has invented or claimed several dishes that are now inseparable from its identity — and locals still argue, in earnest, about the "correct" way to make each one.

Day trip

Indiana Dunes, the only national park within reach

About 80 km southeast of downtown, Indiana Dunes National Park protects nearly 24 km of Lake Michigan shoreline, with sand dunes rising more than 60 meters above the water amid over 1,100 plant species. Reachable in a little over an hour by car or on the South Shore Line train, it's the only national park within easy day-trip range of Chicago — a solid nature break between hiking, beach time and summer swimming.

By length of stay

What to do in Chicago depending on how long you stay

Chicago's airports

Two airports, one clear choice for international flights

When to go

When to visit Chicago?

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FAQ

Frequently asked questions about flights to Chicago