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Suggested Chicago Itineraries

Chicago’s Pilsen neighborhood.

Downtown Chicago is relatively compact, so it’s possible to get a general sense of the city in 1 day (although, of course, you really should spend more than 24 hours here). How you spend your time depends in part on your interests and the weather; you could easily spend 3 days exploring Chicago’s museums, and if you’re here in the winter, that’s probably a lot more appealing than a daylong walking tour. On a sunny summer day, though, you might be tempted to spend an afternoon wandering along the lakefront without any particular destination. In this spirit, I’ve composed the following itineraries, which contain a mix of cultural institutions and scenic walks.

Orientation

Chicago proper has about three million inhabitants living in an area about two-thirds the size of New York City; another five million make the suburbs their home. The Chicago River forms a Y that divides the city into its three geographic zones: North Side, South Side, and West Side. (Lake Michigan is where the East Side would be.) The downtown financial district is called the Loop. The city’s key shopping street is North Michigan Avenue, also known as the Magnificent Mile. In addition to department stores and vertical malls, this stretch of property north of the river houses many of the city’s most elegant hotels. North and south of this downtown zone, Chicago stretches along 29 miles of Lake Michigan shoreline that is, by and large, free of commercial development, reserved for public use as green space and parkland from one end of town to the other.

“The Loop” refers to a core of high-rises surrounded by elevated train tracks;

Finding an Address

Chicago is laid out in a grid system, with the streets neatly lined up as if on a giant piece of graph paper. Because the city itself isn’t rectangular (it’s rather elongated), the shape is a bit irregular, but the perpendicular pattern remains. A half-dozen or so major diagonal thoroughfares make moving through the city relatively easy.

Point zero is located at the downtown intersection of State and Madison streets. State Street divides east and west addresses, and Madison Street divides north and south addresses. From here, Chicago’s highly predictable addressing system begins. Making use of this grid, it’s easy to plot the distance in miles between any two points in the city.

Virtually all of Chicago’s principal north–south and east–west arteries are spaced by increments of 400 in the addressing system—regardless of the number of smaller streets nestled between them—and each addition or subtraction of the number 400 to an address is equivalent to a half-mile. Thus, starting at point zero on Madison Street and traveling north along State Street for 1 mile, you will come to 800 N. State St., which intersects Chicago Avenue. Continue uptown for another half-mile and you arrive at the 1200 block of North State Street at Division Street. And so it goes, right to the city line, with suburban Evanston located at the 7600 block north, 9½ miles from point zero.

The same rule applies when you’re traveling south, or east to west. Thus, starting at point zero and heading west from State Street along Madison and Halsted streets, the address of 800 W. Madison St. would be the distance of 1 mile, while Racine Avenue, at the intersection of the 1200 block of West Madison Street, is 1½ miles from point zero. Madison Street then continues westward to Chicago’s boundary with the nearby suburb of Oak Park along Austin Avenue, which, at 6000 W. Madison, is approximately 7½ miles from point zero.

Once you’ve got the grid figured out, you can look at a map and estimate about how long it will take to walk around any given neighborhood. The other convenient aspect of the grid is that every major road uses the same numerical system. In other words, the cross street (Division St.) at 1200 N. Lake Shore Dr. is the same as at 1200 N. Clark St. and 1200 N. LaSalle St.

Street Maps

Free maps are available at the city’s official visitor information centers at the Chicago Cultural Center and the Chicago Water Works Visitor Center (see “Visitor Information”). You can also print out maps before your trip by visiting the Chicago Convention and Tourism Bureau’s website, www.choosechicago.com.

Neighborhoods in Brief

Downtown

The Loop The Loop refers literally to a core of high-rises surrounded by a rectangular “loop” of elevated train tracks. But when Chicagoans use the term, they’re referring to the city’s downtown, bounded by the Chicago River to the north and west, by Michigan Avenue to the east, and by Roosevelt Avenue to the south. For the most part, the Loop is strictly business, filled with office buildings rather than residential developments. For a suggested walking tour of the Loop.

The North Side

Magnificent Mile North Michigan Avenue from the bridge spanning the Chicago River to its northern tip at Oak Street is known as the Magnificent Mile (or, simply, “Michigan Avenue,” although the street itself stretches much farther). Many of the city’s best hotels and most concentrated shopping can be found here. The area stretching east of Michigan Avenue to the lake is sometimes referred to as “Streeterville”—the legacy of George Wellington “Cap” Streeter. Streeter was an eccentric, bankrupt showman who lived in Chicago in the mid-1880s. Looking for a new way to make money, Streeter bought a steamship with a plan to become a gun runner in Honduras. The steamship ran aground during a test cruise in Lake Michigan, and Streeter left the ship where it was, staking out 200 acres of self-created landfill. He then declared himself “governor” of the “District of Lake Michigan.” True story.

River North Just to the west of the Mag Mile is an old warehouse district called River North. These formerly industrial buildings have been transformed into one of the city’s most vital commercial districts, with many of the city’s hottest restaurants and nightspots; you’ll also find the city’s highest concentration of art galleries here. Large-scale residential loft developments have sprouted on its western and southwestern fringes.

You’ll find many of the city’s hottest nightspots in River North.

The Gold Coast Some of Chicago’s most desirable real estate and historic architecture is found along Lake Shore Drive, between Oak Street and North Avenue and along the adjacent side streets. Despite trendy pockets of real estate that have popped up elsewhere, the moneyed class still prefers to live by the lake. On the neighborhood’s southwestern edge, around Division and Rush streets, a string of raucous bars and late-night eateries contrasts sharply with the rest of the area’s sedate mood. For a suggested walking tour of the neighborhood.

Old Town West of LaSalle Street, principally on North Wells Street between Division Street and North Avenue, is the residential district of Old Town, which boasts some of the city’s best-preserved historic homes (a few even survived the Great Chicago Fire of 1871). This area was a hippie haven in the 1960s and ’70s; now the neighborhood is one of the most expensive residential areas in the city. Old Town’s biggest claim to fame, the legendary Second City comedy club, has served up the lighter side of life to Chicagoans for more than 30 years.

Lincoln Park Chicago’s most popular residential neighborhood for young singles and urban-minded families is Lincoln Park. Stretching from North Avenue to Diversey Parkway, it’s bordered on the east by the huge park of the same name, which is home to one of the nation’s oldest zoos (established in 1868). The trapezoid formed by Clark Street, Armitage Avenue, Halsted Street, and Diversey Parkway also contains many of Chicago’s liveliest bars, restaurants, retail stores, music clubs, and off-Loop theaters—including the nationally acclaimed Steppenwolf Theatre Company.

Lakeview & Wrigleyville Midway up the city’s North Side is a one-time blue-collar, now mainstream middle-class quarter called Lakeview. It has become the neighborhood of choice for many gays and lesbians, recent college graduates, and residents priced out of Lincoln Park. The main thoroughfare is Belmont Avenue, between Broadway and Sheffield Avenue. Wrigleyville is the name given to the neighborhood in the vicinity of Wrigley Field—home of the Chicago Cubs—at Sheffield Avenue and Addison Street. Not surprisingly, the ball field is surrounded by sports bars and memorabilia shops.

Uptown & Andersonville Uptown, which runs along the lakefront as far north as Foster Avenue, has traditionally attracted waves of immigrants. While crime was a major problem for decades, the area has stabilized, with formerly decrepit buildings being converted into—you guessed it—condominiums. Vietnamese and Chinese immigrants have transformed Argyle Street between Broadway and Sheridan Road into a teeming market for fresh meat, fish, and all kinds of exotic vegetables. Slightly to the north and west is the old Scandinavian neighborhood of Andersonville, whose main drag is Clark Street, between Foster and Bryn Mawr avenues. The area has an eclectic mix of Middle Eastern restaurants, a distinct cluster of women-owned businesses, and a burgeoning colony of gays and lesbians.

Lincoln Square West of Andersonville and slightly to the south, where Lincoln, Western, and Lawrence avenues intersect, is Lincoln Square, a neighborhood that still retains traces of Chicago’s once-vast German-American community. The surrounding leafy residential streets have attracted many families, who flock to the Old Town School of Folk Music’s theater and education center, a beautiful restoration of a former library building.

Rogers Park Rogers Park, which begins at Devon Avenue, is located on the northern fringes of the city bordering suburban Evanston. Its western half has been a Jewish neighborhood for decades. The eastern half, dominated by Loyola University’s lakefront campus, has become the most cosmopolitan enclave in the entire city: African Americans, Asians, East Indians, and Russian Jews live side by side with the ethnically mixed student population drawn to the Catholic university. The western stretch of Devon Avenue is a Midwestern slice of Calcutta, colonized by Indians who’ve transformed the street into a veritable restaurant row serving tandoori chicken and curry-flavored dishes.

The West Side

West Loop Also known as the Near West Side, the neighborhood just across the Chicago River from the Loop is the city’s newest gentrification target, as old warehouses and once-vacant lots have been transformed into trendy condos and stylish restaurants. Chicago’s old Greektown, still the Greek culinary center of the city, runs along Halsted Street between Adams and Monroe streets. Much of the old Italian neighborhood in this vicinity was the victim of urban renewal, but remnants still survive on Taylor Street. The same is true for a few old delis and shops on Maxwell Street, dating from the turn of the 20th century when a large Jewish community lived in the area.

Bucktown/Wicker Park Centered near the intersection of North, Damen, and Milwaukee avenues, this resurgent area has hosted waves of German-, Polish-, and, most recently, Spanish-speaking immigrants (not to mention writer Nelson Algren). In recent years, it has morphed into a bastion of hot new restaurants, alternative culture, and loft-dwelling yuppies, although the neighborhood still feels somewhat gritty. The terms Bucktown and Wicker Park are often used interchangeably, but Bucktown is technically the neighborhood north of North Avenue, while Wicker Park is to the south. For a walking tour of the area.

The South Side

South Loop The generically rechristened South Loop area was Chicago’s original “Gold Coast” in the late 19th century, with Prairie Avenue (now a historic district) as its most exclusive address. But in the wake of the 1893 World’s Columbian Exposition in Hyde Park, and continuing through the Prohibition era of the 1920s, the area was infamous for its Levee vice district, home to gambling and prostitution, some of the most corrupt politicians in Chicago history, and Al Capone’s headquarters at the old Lexington Hotel. However, in recent years, its prospects have turned around. The South Loop—stretching from Harrison Street’s historic Printers Row south to Cermak Road (where Chinatown begins), and from Lake Shore Drive west to the south branch of the Chicago River—is now one of the fastest-growing residential neighborhoods in the city.

Pilsen Originally home to the nation’s largest settlement of Bohemian-Americans, Pilsen (named for a city in what’s now the Czech Republic) was for decades the principal entry point in Chicago for immigrants of every ethnic background. Centered at Halsted and 18th streets just southwest of the Loop, Pilsen now contains one of the largest Mexican-American communities in the U.S. This vibrant and colorful neighborhood, which was happily invaded by the outdoor mural movement launched years earlier in Mexico, boasts a profusion of authentic taquerías and bakeries. The artistic spirit that permeates the community isn’t confined to Latin American art. In recent years, artists of every stripe, drawn partly by the availability of loft space in Pilsen, have nurtured a small but thriving artists’ colony here.

Hyde Park Hyde Park is like an independent village within the confines of Chicago, right off Lake Michigan and roughly a 30-minute train ride from the Loop. Fifty-seventh Street is the main drag, and the University of Chicago—with all its attendant shops and restaurants—is the neighborhood’s principal tenant. The most successful racially integrated community in the city, Hyde Park is an oasis of furious intellectual activity and liberalism that, ironically, is hemmed in on all sides by neighborhoods suffering some of the highest crime rates in Chicago. Its main attraction is the world-famous Museum of Science and Industry.

The Best of Chicago in 1 Day

The day begins with a walking tour of the Loop, which is the best way to get your bearings (and understand why Chicago’s architecture is world famous). Then you can squeeze in a quick visit to one of the city’s preeminent museums before strolling along Michigan Avenue, Chicago’s most famous thoroughfare, which takes you to the ritzy Gold Coast neighborhood. If possible, follow this itinerary on a weekday, when downtown offices are open and the sidewalks buzz with energy. This route works fine on weekends as well, but you won’t experience quite the same big-city rush. Start: Green, Orange, Brown, or Purple lines to Adams, or Red Line to Jackson.

1 Chicago Architecture Foundation

Start your day with the Chicago Architecture Foundation’s “Historic Downtown: Rise of the Skyscraper” tour, which begins daily at 10am year-round. The 2-hour walking tour takes you to the oldest high-rises in the Loop, and the docents explain why these early office buildings were revolutionary. Sure, you’ll get a basic architecture education, but this is also a great way to get a sense of the Loop’s layout and dramatic canyonlike vistas. (Another popular tour, “Modern Skyscrapers,” starts daily at 1pm.)

2 The Art Institute ★★★

Across the street from the Chicago Architecture Foundation stands one of the city’s most prestigious cultural institutions; if you have time for only one museum while you’re here, this is the one to visit. Since you’ve got limited time, head right for the two must-see exhibits: first, the world-famous Impressionist collection, followed by the 20th-century American modern art gallery, which houses masterpieces such as Edward Hopper’s Nighthawks.

Edward Hopper’s Nighthawks at the Art Institute of Chicago.

3 Millennium Park ★★★

Just north of the Art Institute is one of the city’s most popular gathering spots. Check out the massive video-screen faces on the Crown Fountain, then take a walk around (and under) Anish Kapoor’s bean-shaped sculpture, Cloud Gate. The Pritzker Music Pavilion, designed by Frank Gehry, features the architect’s signature ribbons of silver steel; Gehry also designed the adjoining serpentine bridge.

Skaters on Millennium Park’s rink.

4 Park Grill ★★

In the winter, this restaurant overlooks Millennium Park’s ice-skating rink; come summer, the rink transforms into an outdoor cafe, perfect for sipping a drink and admiring the skyline. Stay for a full meal or grab a sandwich to go. 11 N. Michigan Ave. 312/521-PARK (521-7275).

5 Michigan Avenue Bridge

Walk north along Michigan Avenue and you’ll come to this bridge, which spans the Chicago River. Stop here for a great photo op—on a nice day, you’ll be joined by plenty of other visitors doing the exact same thing.

6 The Magnificent Mile

The 14-block stretch of Michigan Avenue from the river to Oak Street, known as the “Magnificent Mile,” is shopping central, a dense concentration of high-rise malls, designer boutiques, and practically every mass-market clothing brand. Even if you’re not a shopper, it’s worth a stroll; busy at almost all hours, it’s great for people-watching. Some Chicagoans dismiss the Mag Mile as too touristy, but I think walking here makes you feel like you’re part of a vibrant metropolis.

The Pritzker Pavilion features Frank Gehry’s signature ribbons of steel.

7 Hancock Observatory ★★

This may only be Chicago’s third-tallest building, but the view from the top is spectacular: In the right weather conditions, you can see all the way to three other states (Wisconsin, Indiana, and Michigan). The “talking telescopes” help you get your bearings by pointing out landmarks in each direction.

8 Oak Street Beach

Where Michigan Avenue merges into Lake Shore Drive at Oak Street, head down the underpass to get to Oak Street Beach, a curved stretch of sand that’s a summertime hot spot and a great background for photos. Bikers, skaters, and joggers fill the paths, while kids play in the sand. Think of it as Chicago’s own miniresort getaway—just don’t plan on swimming in the frigid water.

9 Third Coast

If you’re tired of generic chain coffeehouses (of which Chicago has plenty), stop by this somewhat shabby lower-level cafe that welcomes both well-heeled locals and the occasional starving artist. In addition to the usual lattes and muffins, there’s a full lunch and dinner menu, and wine and beer are available. 1260 N. Dearborn St. 312/649-0730.

10 The Gold Coast

To get an idea of how Chicago’s wealthiest live, take a stroll through this neighborhood of historic town homes (including the original Playboy Mansion, at 1340 N. State Pkwy.). The tranquil, tree-lined streets are only a few blocks away from Michigan Avenue, but they feel like a different city. (For a suggested walking tour.) Finish up the night with dinner at one of the many restaurants in River North, or catch a show and discover Chicago’s vibrant theater scene.

The original Playboy Mansion.

The Best of Chicago in 2 Days

After Day 1, you should be familiar with downtown Chicago. Now it’s time to explore at least part of the Museum Campus, home to three major museums. Although I recommend the Field Museum for this itinerary, you could certainly substitute the nearby Shedd Aquarium or Adler Planetarium, depending on your interests. The first part of this day keeps you firmly in tourist territory, but you’ll journey off the beaten track later in the day when you wander through Wrigleyville and get a sense of how real Chicagoans live. Start: Bus no. 6, 10, 12, 130, or 146 to Roosevelt Road and Lake Shore Drive.

1 Field Museum of Natural History ★★★

You’ll feel as though you’ve entered a truly grand place when you walk into the museum’s massive Stanley Field Hall and come face to face with Sue, the largest Tyrannosaurus rex fossil ever discovered. The Field Museum is one of those classic something-for-everyone institutions where you can wander for hours. The Inside Ancient Egypt exhibit is more than just mummies: It’s a complete re-creation of ancient daily life, including a marketplace, royal barge, and religious shrines (with lots of hands-on activities for kids). The second-floor African and South Pacific exhibits are also worth a stop, with beautifully designed interactive displays. But the Fields also has a certain timeless quality: The old-fashioned animals-of-the-world dioramas, for example, have remained unchanged for decades.

A hands-on exhibit at the Field Museum of Natural History.

2 Buckingham Fountain

This grand stone fountain is one of the city’s iconic structures. (If you’re a sitcom fan, you might recognize it from the opening credits of Married with Children.) Try to get here on the hour, when jets of water spurt dramatically into the sky. The fountain blazes with colored lights at night, so if you’re staying downtown, it’s also worth a stop after dark. (Note: The fountain is closed Nov–Mar.)

Buckingham Fountain blazes with colored lights at night.

3 Lake Michigan or Chicago River cruise

Departing from a dock at the nearby Shedd Aquarium, Shoreline Sightseeing ★ runs water taxis that cruise north to Navy Pier (daily from Memorial Day to Labor Day). From the pier, you can also catch boats that cruise along the Chicago River all the way to the Sears Tower.

4 Navy Pier

Yes, it’s touristy and crowded, but Navy Pier is also full of energy—and if you stroll all the way to the end, you’ll be rewarded with great views of downtown. If you’re traveling with kids, stopping at Navy Pier is pretty much mandatory; it has a carousel and other carnival-type rides, lots of boats to admire, and the Chicago Children’s Museum.

5 Charlie’s Ale House

Head to the outdoor patio of this casual saloon for a front-row look at Navy Pier’s busy waterfront. Cool off with a drink, or fill up on comfort food classics like burgers or chicken pot pie. 700 E. Grand Ave. 312/595-1440.

From Navy Pier, take the free Navy Pier shuttle to the Grand El station (Red Line), and ride north to the Addison Street stop.

6 Wrigley Field ★★

If you’re a baseball fan, Wrigley is hallowed ground: the second-oldest stadium in the major leagues, home to the perennially jinxed Chicago Cubs. The surrounding blocks are a good place to stock up on Cubs souvenirs. If you want to catch a game, tickets can be tough to come by (the entire season tends to be sold out by Opening Day). Show up an hour or so before a game, and you can sometimes find a season ticket holder trying to sell unused seats (and ticket brokers always have seats available—for a price).

If you’re not staying for a game and would rather explore a residential neighborhood, walk west on Addison Street for 5 blocks until you get to:

7 Southport Avenue

This area is well into the gentrified stage (witness the number of trendy clothing boutiques), but it’s still very much a neighborhood. Wander Southport between Belmont Avenue and Grace Street, and you’ll see young moms pushing designer strollers, singles walking their dogs, and hardly any other tourists. If you’re here in the early evening, you’ll find plenty of low-key, affordable restaurants for dinner. When you’re ready to head back downtown, you can hop on the Brown Line at the Southport stop.

8 Julius Meinl

Run by an Austrian coffee company, this cafe is a mix of Old World and New. Large picture windows make it feel bright and inviting, while the European pastries and coffee (served elegantly on silver trays) are a welcome change from standard chain coffeehouses. 3601 N. Southport Ave. 773/868-1857.

European pastries and coffee at Julius Meinl.

9 Buddy Guy’s Legends ★★

Chicago is the birthplace of “electric blues,” that rocking blend of soulful singing and wailing electric guitars. To experience the city’s most famous form of music, head for Buddy Guy’s Legends in the South Loop, which has the honky-tonk feel of a Southern roadhouse. The owner, blues guitarist and Rock and Roll Hall of Famer Buddy Guy, makes regular appearances; even if he’s not on the bill, the talent level is always top-notch. (If you’re staying on the North Side of the city and would rather stick close to home, try Kingston Mines, Blue Chicago, or B.L.U.E.S.)

The Best of Chicago in 3 Days

For this itinerary, it’s time to escape downtown completely and spend the day on the North Side of the city. You’ll start out in Lincoln Park, which is both an actual park and the name of a popular residential neighborhood, where singles and young families can be seen strolling or jogging along the lakefront paths during nice weather. You’ll also visit two major cultural institutions, both suitable for kids, and then head into a residential neighborhood for some shopping. Start: Bus no. 151 or 156 to North Cannon Drive and Fullerton Parkway.

1 Lincoln Park Zoo ★★★

A beloved local institution, this zoo won’t dazzle you a la San Diego, but it does a good job of covering all the bases, with a mix of indoor habitats and naturalistic outdoor environments (plus, did I mention it’s free?). Don’t miss the Regenstein African Journey exhibit (which re-creates both a tropical jungle and a dusty African savanna) and the internationally renowned Great Ape House. If you have kids, stop at the Children’s Zoo, where a unique climbing structure gives little ones 2 and older a chance to release some energy.

2 Farm-in-the-Zoo

Just south of the zoo, this re-creation of a working farm gets children in touch (literally) with animals. The highlight for many little ones is the giant John Deere tractor; you’ll usually find a line of kids waiting for their turn to sit behind the massive steering wheel (along with parents waiting to snap a picture).

Farm-in-the-Zoo’s main attraction, the giant John Deere Tractor.

3 Big Cats Café

This cafe, located on the roof of the zoo’s gift shop, has outdoor seating and panoramic views over the zoo. You can order the usual hot dogs and fries, but there’s also a selection of more health-conscious wraps. 2200 N. Cannon Dr. 312/742-2000.

4 North Avenue Beach

Come summer, this is Lincoln Park’s prime playground—a place to jog, play volleyball, build sandcastles, or simply pose. Even in August, the water is usually icy, but if you want to at least dip your feet in Lake Michigan, this wide stretch of sand is the place to do it. Just south of the beach, a grassy stretch of park offers picture-perfect views of downtown.

Take a taxi to the corner of Halsted Street and Armitage Avenue.

5 Armitage Avenue

To call this the city’s chicest shopping strip isn’t meant as a put-down to Michigan Avenue; while the Mag Mile goes for big and showy, the boutiques along Armitage tend to be smaller and more personal (most are independently owned rather than chain stores). You’ll find an especially appealing selection of home decor stores and gift shops with eclectic selections of well-designed merchandise. Wander the surrounding side streets to see the neighborhood’s eclectic mix of historic homes and modern mansions.

Armitage Avenue’s chic shops tend to be small and personal.

If you’re ready to wind down, you’ll find plenty of restaurants nearby or in adjacent Old Town. But if you’d like to explore one more neighborhood, take a taxi to the corner of North Avenue and Damen Avenue, then walk north along Damen.

6 Bucktown

If you’re not shopped out yet, finish up the day with a walk through Bucktown, home to the city’s highest concentration of edgy clothing boutiques. It feels grittier than Armitage Avenue, and that’s part of the appeal for the cool kids who live here.

7 Northside Café

Bucktown’s unofficial neighborhood hangout, this low-key cafe is a sandwich spot by day and a bustling bar by night. When the weather’s nice, grab a seat on the outdoor patio and people-watch with everyone else. 1635 N. Damen Ave. 773/384-3555.

8 Improv Comedy

Although it’s best known for Second City, Chicago is home to a number of excellent improv comedy troupes. You can catch rising stars before they land their own sitcom deals. Second City is the big man on campus, while iO is the slightly scrappier and more creative bunch. If you’re here with older kids or teens, catch the family-friendly ComedySportz.