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By: Darren Frei
Chicago stands a strong chance of being everyone’s kind of town. With world-class museums and performing arts venues, legendary jazz and blues clubs, more than 7000 restaurants serving everything from haute cuisine to hot dogs, and 29 magnificent miles of lakefront, the “City of Big Shoulders” offers something for everyone. Whether taking in a free concert at Chicago’s gleaming new Millennium Park, indulging in a bit of retail therapy on Michigan Avenue, or diving into one of the city’s signature deep-dish pizza pies, visitors can expect a diverse array of cosmopolitan creature comforts served up with a friendliness and charm that’s lacking in bigger cities like New York.

Chicago’s most obvious attraction is its impressive skyline. The dazzling architectural heritage of this Midwest metropolis can be owed, at least in part, to a cow. After the Great Chicago Fire of 1871 (which started, according to legend, when Mrs. O’Leary’s cow kicked over a lantern) the city was rebuilt on a massive scale by some of the world’s most renowned architects. Frank Lloyd Wright, Mies van der Rohe, and “father of the skyscraper” William Le Baron Jenney have all left their marks on the city’s skyline. Acclaimed Spanish architect Santiago Calatrava will join their ranks in 2010 when his 150-storey Chicago Spire, a twisting condominium complex on Lake Michigan, becomes North America’s tallest building.

Most major attractions are centrally located, making it easy to pack a variety of activities into a whirlwind weekend without running yourself ragged. On a three-day visit, you’ll be able to take in the downtown area’s key museums, parks, and sky-high observation decks, while a weeklong stay provides an opportunity to explore the city’s diverse patchwork of multiethnic communities as well as neighboring suburb Oak Park, home of the world’s largest collection of homes designed by Frank Lloyd Wright, and Illinois state capital Springfield (a three-hour drive), which is home to the new Abraham Lincoln Presidential Museum.



The best way to savor Chicago is by foot, but the city’s extensive and efficient public transportation system – which carries around 1.5 million passengers a day on subways, buses, and elevated trains (known simply as “the El”) – provides easy access between multiple points downtown, outlying neighborhoods, and the suburbs.


During the summer, the City of Chicago Department of Transportation offers free trolley rides (daily departures every 20 min; 312/744-5000) around downtown Chicago. Keep in mind that the trolleys don’t have air conditioning, so humid summer days can be taxing.

Visitors looking for a local’s perspective can participate in the city’s new Chicago Greeter program ( These volunteer guides can escort groups of up to six people, free of charge, for two to four-hour tours of specific neighborhoods and themes (everything from Irish American heritage sites to famous locations in literature). Reservations for specific tours should be made at least a week in advance, but “Instagreeters,” tour guides who lead visitors on an hour-long visit of the Loop and North Michigan Avenue, are available Friday through Sunday at the Chicago Cultural Center (77 E. Randolph St.) on a first come, first served basis.

For discounts on museums, restaurants, shopping centers, performing arts venues, and other attractions throughout the city, along with a list of free events and attractions, get the Chicago Guidebook of Special Values. Just print the online voucher available at and redeem it at one of two Chicago Visitor Information Centers (Chicago Cultural Center, 77 E. Randolph St. at Michigan Ave.; or Chicago Water Works, 163 E. Pearson at Michigan Ave). These centers are open daily and provide knowledgeable ambassadors who are ready to answer all of your questions and help plan your itinerary.

For an introduction to many of the city’s most notable buildings, we highly recommend the popular ninety-minute river cruise offered by the Chicago Architecture Foundation (Chicago River at Michigan Ave. and lower Wacker Dr.; various daily departures; $25-$27; The CAF also offers around 85 other tours by boat, bus, bike, and on foot.

Main Sights
The Chicago River, which runs through the city’s downtown financial district (The Loop) divides the city into three geographic areas: North Side, South Side, and West Side. On the east, the shoreline of Lake Michigan provides 29 miles of mostly uninterrupted public green space and parkland.

Kick off your visit with a lakefront cruise to orient yourself with the city’s layout. Shoreline Sightseeing Company offers thirty-minute skyline boat tours from multiple locations (daily June-Aug every 30 mins 10am–10pm; daily May & Sept hourly 11am–5pm; Apr, Oct, & Nov Sat & Sun hourly 11am–5pm; $12;

Back on land, The Loop is also a logical place to begin exploring America’s third-largest city. Home of the city’s most famous skyscrapers, an assortment of cultural institutions, and a high concentration of outdoor public sculptures, you could easily spend one full day—indeed, an entire weekend—in and around this bustling area.

Start off with a trip to the Skydeck (daily May-Sept 10am–10pm; Oct-Apr 10am–8pm; $11.95; on the 103rd floor of the 110-storey Sears Tower, currently the tallest building in the United States. On a clear day, you’ll be rewarded with spectacular views reaching as far out as Michigan, Indiana, and Wisconsin. A recent $4 million renovation has added historical exhibits, high-powered telescopes, and interactive kiosks that point out Chicago landmarks. The best time to visit is after 4pm when most of the crowds will have dissipated.

Another landmark building with jaw-dropping views is the 100-storey John Hancock Center (daily 9am–11pm; $9.95;, which features Chicago’s only open-air observation deck on the 94th floor – step out here and you’ll see why they call it the windy city.

After soaring to the stratosphere inside these modern marvels, step back in time at the city’s earlier architectural landmarks. The 34-storey gothic style Tribune Tower (1925) and the 30-storey Spanish revival style Wrigley Building (built in stages between 1920 and 1931) are located in the southern end of the high-end shopping district known as the Magnificent Mile, which runs along Michigan Avenue from the Chicago River to Lake Michigan. The walls of the Tribune Tower, home of the Chicago Tribune newspaper, are embedded with authentic pieces of famous buildings including the Parthenon, the Great Pyramid, the Taj Mahal, and Westminster Abbey. While the tower has all of the traditional elements of a skyscraper, it also includes classical elements such as flying buttresses and spires. The triangular Wrigley Building, home to the namesake chewing gum company, is covered with 250,000 terracotta tiles, giving it a gleaming white appearance. You can get a great view of both from the Michigan Avenue Bridge.

Though frequently upstaged by the skyscrapers, Chicago’s numerous public sculptures are worth noting as well. The city is a veritable open-air museum, with outdoor public art by 20th-century art stars like Calder, Chagall, Miró, and, most famously, Picasso. Standing in front of Daley Plaza, in the heart of the Loop, is the 162-ton steel sculpture known simply as The Picasso, a face rendered in the artist’s primitive style. It was unveiled in 1967 to much public scorn, but has since become one of the city’s most recognizable icons.

If you’re traveling with kids, don’t miss Navy Pier, located east of downtown, along Lake Michigan. Designed as a shipping and recreational facility in 1916, the pier now encompasses over 50 acres of parks, gardens, attractions, restaurants, and shops. Take a ride on the famous 150-foot Ferris Wheel (Sun–Thurs 10am–10pm; Fri & Sat 10am–midnight; $5;, modeled after the very first Ferris Wheel built for Chicago’s 1893 World Colombian Exposition.

Whether cheering for “da Bears” or “da Cubs,” Chicagoans are die-hard sports fans – and, depending on the season, you can join in the raucous fun. Home of The Bears football team, Soldier Field( was recently renovated with an ultra-modern glass facade that incorporates the original Doric colonnades built between 1922 and 1928. The second-oldest baseball stadium in the majors, Wrigley Field, is home to the Chicago Cubs ( and dates from 1914. The 2005 World Series Champions, the White Sox (, play at U.S. Cellular Field (formerly Comiskey Park) on the city’s south side.

If you’re more interested in the rousing sport of daytime TV, try your luck at becoming a studio-audience member at The Oprah Winfrey Show (, which tapes at Harpo Studios (1058 W. Washington St.), ten-minutes west of The Loop, in the near west side of Chicago. Reservations are available almost exclusively by phone, but you can request last-minute reservations by e-mailing the Audience Department. Keep in mind that demand far exceeds supply (and even if you do get in, there’s no guarantee you’ll catch celebrities jumping on couches or Oprah taking swings at the latest author to scorn her).

Museums & Galleries
If the weather doesn’t cooperate with your well-laid vacation plans, you can duck into one of the city’s many museums. Most museums offer free admission one day per week (for a full schedule, visit

Facing Michigan Avenue, and part of Museum Campus in Grant Park, The Art Institute of Chicago (daily Mon–Wed 10.30am–5pm, Thurs & Fri 10.30am–9pm, Sat & Sun 10am–5pm; $12; houses over 2000 paintings and sculptures in its collection of European art, including the largest collection of Impressionist art outside the Louvre; the most famous of these works is George Seurat’s pointillist masterpiece, La Grande Jatte. Other major collections include sculpture, photography, decorative arts, and Asian, African, and American art. The museum is currently constructing a modern $200-million wing – designed by architect Renzo Piano – that will increase gallery space by 33% when it opens adjacent to Millennium Park in 2009.

Other Museum Campus attractions include the Adler Planetarium (daily Memorial Day to Labor Day 9.30am–6pm; Sept–May 9.30am–4.30pm; $16;, which has three floors of exhibits on astronomy, space exploration, telescopes, and navigation. StarRider, its 60,000-square-foot domed theater, can faithfully reproduce every aspect and movement of the night sky. Sue, the world’s largest known Tyrannosaurus Rex fossil, can be found at the Field Museum (daily Memorial Day to Labor Day 8am–5pm; Sept–May 9am–5pm; $12;, while over 650 species of aquatic animals live at the Shedd Aquarium (Memorial Day to Labor Day 9am–6pm; Sept–May 9am–5pm; $23;, including over 24 sharks at Wild Reef, a 400,000 gallon tank with 20 different habitats.

Located just off Michigan Avenue, the Museum of Contemporary Art (Tues 10am–8pm; Wed–Sun 10am–5pm; $10; free Tues; contains over 6000 paintings, sculpture, photography, video, film, and installations from 1945 to the present, including work by Andy Warhol, Chuck Close, Francis Bacon, Jeff Koons, and many more. The museum cafe, Puck’s, features a great seasonal lunch menu created by famed chef Wolfgang Puck.

Tired of looking at art and not being able to take it off the wall? Just north of the Chicago River, the River North Gallery District is home to nearly 70 world-class art and antiques galleries, the largest concentration of art galleries outside of Manhattan. A neglected urban wasteland in the mid-’70s, the area is now one of the most vibrant neighborhoods in Chicago, with modern condo buildings, vintage loft buildings, innovative restaurants, and chic home decor shops.

Parks & Gardens
With over 7300 acres of parkland comprising 552 parks and 33 public beaches, it stands to reason that Chicago’s official motto is Urbs in Horto (City in a Garden). The most stunning new public space in Chicago, if not the entire nation, is Millennium Park ( located along Michigan Avenue between Randolph and Monroe streets. Opened in 2004, the centerpiece of the 24.5-acre park, the Jay Pritzker Pavilion, is a band shell designed with Frank Gehry’s signature billowing metal facade. Don’t miss a photo op at Cloud Gate (known locally as “The Bean” for its jelly-bean shape), an enormous elliptical blob of highly polished stainless steel that reflects the city’s skyline – and the amused expressions of all those who gaze in it. The park’s Bike Station (, located in the park’s northeast corner, offers bikes for rental by the hour, day, or week and provides secure bicycle parking, lockers, showers, towel service, and free bicycle valet parking during summer performances at Millennium Park and Grant Park festivals. If you do rent a bike, head out along the Lakefront Trail, a paved path that stretches 18 miles along Lake Michigan, providing cool lake breezes and stunning skyline views.

From Millennium Park, visitors can walk to one of the city’s more established public spaces, Grant Park, via a new serpentine, stainless steel footbridge (also designed by Frank Gehry). Dubbed “Chicago’s Front Yard,” Grant Park, is situated on the Lake Michigan waterfront. The park’s main focal point is the 1927-built Buckingham Fountain (instantly recognizable from the opening of the television series Married with Children), which shoots a stream of water 150 feet into the air, accompanied by lights and music (hourly dusk–10pm), spring through early fall. The park is also home to what is known collectively as the Museum Campus – which includes the Art Institute of Chicago, the Field Museum of Natural History, the Shedd Aquarium, and the Adler Planetarium (see Museums & Galleries, above).

Located on Chicago’s north side, the 1208-acre Lincoln Park stretches from Ardmore Avenue south to North Avenue. Its biggest attraction is the Lincoln Park Zoo (daily 9am–6pm; free;, one of the only zoos in the country open free of charge. Take a spin on the Endangered Species Carousel ($2), which features a handcrafted menagerie of 48 rare and endangered animals, or cruise in a swan-shaped boat around the South Lagoon, with the John Hancock tower looming above (June–Sept daily 10am–dusk; $16).

During the summer, there’s no sexier (nor more crowded) place to see and be seen than Oak Street Beach, a lakeside oasis with volleyball courts, paths for bikers and in-line skaters, and plenty of sand for bikini-clad sunbathers. Located just north of the Magnificent Mile, the wide beach’s main points of access are from underground tunnels at Oak Street, Division Street, and Chicago Avenue.

If you have some extra time to wander beyond the main attractions of downtown, head seven miles south of the Loop to Hyde Park, which became Chicago’s first suburb when it was settled in 1850. This south side neighborhood is home to the University of Chicago, Frank Lloyd Wright’s Robie House, and the popular Museum of Science and Industry (Mon–Sat 9.30am–5:30pm; Sun 11am–5:30pm; $11; Explore the college campus, take a walk down Lake Shore Drive and marvel at the impressive apartment houses, or just sit at an outdoor cafe and soak in the energy of this cosmopolitan melting pot.

Nine miles west of the Chicago Loop, leafy Oak Park (another one of Chicago’s first suburbs) is where you’ll find the birthplace of Ernest Hemingway, the first home and studio of Frank Lloyd Wright, and the largest concentration of Wright homes in the world. The homes in this neighborhood span the early Victorian period, through the Prairie School of Architecture, and on to the Art Deco period. First, tour the Victorian Hemingway Birthplace Home (339 N. Oak Park Ave.; Mon–Fri & Sun 1pm-5pm, Sat 10am–5pm; $7;, where the author was born in 1899, to learn about his early family life, then visit the Ernest Hemingway Museum (200 N. Oak Park Ave.; same hours) to view rare photos, his childhood diary, letters, early writings, and other memorabilia. Before you leave the area be sure to tour the one-of-a-kind Frank Lloyd Wright Home & Studio (leaves from the Ginkgo Tree Bookshop, 951 Chicago Ave.; Mon–Fri 11am, 1pm & 3pm; Sat–Sun every 20 minutes 11am–3.30pm; $12;, which served as Wright’s private residence for the first 20 years of his career (1889 to 1909). Constantly tinkering with the walls, ceilings, and rooms, Wright would experiment with design concepts here before sharing them with his clients; the guided tour lasts 45 to 60 minutes.

A three-hour drive from Chicago, Springfield is the capital of Illinois. Criticized by some as a theme-park simplification of history, the Abraham Lincoln Presidential Library and Museum (212 North Sixth St.; Mon–Tue & Thur–Sun 9am–5pm, Wed 9am–8.30pm; $7.50; provides an entertaining and educational look at the life and times of the 16th president. Interactive exhibits and theatrical special effects, including an “odometer of death” that calculates the mounting casualties on both sides of the four-year Civil War and a reproduction of the White House Kitchen are big draws here, as is the signed copy of the Emancipation Proclamation in the library.


A diverse array of lodging options abound in Chicago, from the grand and luxurious hotels of Magnificent Mile to nearby boutique properties and budget options geared toward value-conscious travelers.

The best luxury options can be found in the Magnificent Mile and the Loop. Boasting a blend of “Far-Eastern graciousness and Midwestern hospitality,” The Peninsula ( opened to universal acclaim in 2001; set in the heart of the Magnificent Mile, it features 339 spacious guestrooms and suites furnished in a magnificent classical style, with marble bathrooms, flat-screen TVs, and high-speed internet access. Visiting celebrities are known to frequent The Four Seasons (; among its 343 elegant guest rooms is the Author Suite, which includes personalized editions from luminary guests like Stephen King, Margaret Thatcher, Oliver Stone, and Anne Rice. Opened in 1920, The Drake ( is a city landmark, a symbol of white-glove elegance located at the end of the Magnificent Mile; its 535 recently renovated rooms include 74 opulent suites.

In the moderate range, the brand-new boutique-chic James Hotel ( is a hip addition to the River North neighborhood just off the Magnificent Mile; its 297 guest rooms feature flat-screen plasma TVs, 300-thread count sheets, designer furniture, complimentary wireless Internet service, and a stereo system with iPod dock. Voted “best new building in Chicago” by the American Institute of Architects, the prism-shaped Sofitel Chicago Water Tower ( offers spectacular views of the John Hancock tower from many of its 415 guest rooms. Directly overlooking Lake Michigan, the W Hotel ( touts 520 deluxe guest rooms with oak shutters that open onto panoramic views of the lake and the city; its rooftop lounge, Whiskey Sky, is where the “in crowd” hangs.

If you’re on a tighter budget, the city offers many affordable lodging options. Hotel Monaco ( offers 192 rooms at reasonable rates considering its prime location near the Art Institute of Chicago and Millennium Park; like other Kimpton properties, this hotel is pet-friendly, and if you don’t have one, they’ll supply you with a goldfish to call your own. Another option, the 150-room Cass Hotel (, may not have the most stylish rooms, but it’s clean, comfortable, affordable, and within walking distance of the Magnificent Mile. Also great value is the 15-storey Red Roof Inn (, which has a newly redesigned lobby, parlor room, and reception area.


Don’t forget to pack your appetite. With incredible four-and five-star restaurants, innovative fusion hot spots, the best deep-dish pizzerias in the world (the pie was invented here!), and a McDonald’s furnished with chairs by Le Corbusier, Chicago offers an array of dining options, from ultra-high-end to super budget.

Among our favorite destination restaurants is Gibson’s Bar & Steakhouse (1028 N. Rush St.; 312/266-8999; A Chicago institution for over two decades, Gibson’s is where Chicago’s elite and powerful go to lunch, dine, and smoke cigars. Everything is oversized – the drinks, the steaks, the lobsters, the desserts, and even the booths – and cuts of beef range from the chopped steak ($13.75) to the porterhouse ($73.25); be sure to reserve ahead. One of the city’s hottest new restaurants is Sushisamba Rio (504 N. Wells St.; 312/595-2300;, which tickles taste buds with Peruvian-Brazilian-Japanese fusion cuisine and delights the eyes with festive Carnaval-colored design scheme; start with the South American beef maki roll before moving on to a delicious molho. Alinea (1723 N. Halsted St.; 312/867-0110; wins us over with its ultra-sleek interior and sumptuously prepared dishes by Chef Grant Achatz, formerly of French Laundry, in Napa; we recommend the tasting menu ($125), which features Kobe beef with honeydew and cucumber and black cod with vanilla, artichoke, and “pillow of orange air.”

The following mid-range eateries offer exceptional menus that won’t break your budget. With decor reminiscent of 1920s Saigon, Le Colonial (937 N. Rush St.; 312/255-0088; is an excellent French-Vietnamese restaurant set in a vintage two-storey rowhouse; appetizers include grilled shrimp wrapped around sugar cane while a signature entree, Ca Chien Saigon, involves a whole red snapper seared in a light spicy and sour glaze. Brasserie Jo (59 W. Hubbard St.; 312/595-0800; is an authentic French brasserie with classics like onion soup gratinee, provençal tartes flambées (Alsacian-style pizza), and steak frites. For arguably the best Sunday Brunch in town, head to Lula Cafe (2537 N. Kedzie Blvd.; 773/489-9554;; menu items include stuffed brioche French toast with berries and rhubarb; grilled shrimp eggs Florentine; and whole-grain pinenut pancakes with sweet cream, peaches, and candied pinenuts. The setting is just as delicious, with vintage modern furnishings and paintings by local artists on the walls.

The best cheap eats in town include Pizzeria Uno (29 E. Ohio St.; 312/321-1000), the establishment that invented the Chicago-style deep-dish pizza pie over 60 years ago; the hostess will take your order while you stand in line because the pies take 45 to 60 minutes to bake. Normally we would advise you to steer clear of Big Macs and fries, but the new two-storey flagship McDonald’s (600 N. Clark St.; 312/867-0455), a 24,000 square-foot behemoth in downtown Chicago, is worth checking out regardless for its “living room” furnished with leather furniture by Mies van der Rohe and Le Corbusier; onsite Internet web stations also allow for music downloading and instant photo printing capabilities. Located on Chicago’s South Side, Harold’s Chicken Shack (636 S. Wabash Ave.; 312/362-0442) specializes in greasy (and delicious) fried chicken with fiery hot sauce; you can order it dark or white, by the quarter or the half, and each order comes with fries, bread, and coleslaw.


From legendary blues clubs and jazz venues to sleek martini bars and cutting-edge alternative music joints, the after-dark options in Chicago will satisfy any visiting night owl. Less style-conscious than New York or Los Angeles, the Chicago club scene has a friendly and welcoming reputation. Most bars close at 2am but can stay open an extra hour on Saturdays.

Live Music
Chicago offers a wide assortment of legendary blues and jazz clubs. Don’t miss Kingston Mines (2548 N. Halsted St.;, a Chicago blues institution – open since 1968 – that encourages its patrons to “hear the blues, drink booze, and eat food” as late as 4am (5am on Saturdays); its two stages pump out the blues seven days a week. Blue Chicago (736 N. Clark St.; highlights female blues singers, and even hosts a Women’s Festival every year on the second weekend of May. In addition to great live blues and impromptu acts by visiting rock stars, Buddy Guy’s Legends (754 S. Wabash Ave.; offers a sizable collection of blues memorabilia on the walls and a tasty menu that includes shrimp Creole, jambalaya, and barbecue ribs.

An upscale jazz club, Green Dolphin Street (2200 N. Ashland Ave.; hosts all kinds of acts, from traditional jazz to Latin and big band. Open since 1947, The Jazz Showcase (59 W. Grand Ave.; has hosted the likes of Charlie Parker, John Coltrane, and Betty Carter; the jazz aficionados that frequent this joint don’t appreciate talking over the sets.

Live alternative rock acts have had a home at Metro (3730 N. Clark St.; since 1982. Trent Reznor, Ministry, R.E.M., Liz Phair, Pearl Jam, The Smashing Pumpkins, Moby, the White Stripes, Fat Boy Slim, and the Yeah Yeah Yeahs have all cut their teeth in this old auditorium. Admission to Smart Bar, a basement dance club in the same location, is free with a ticket to a Metro show.

An assortment of late-night libations can be found in the River North Gallery District. Martini Ranch (311 W Chicago Ave., 312/335-9500) offers a dangerous collection of 40 different martinis. We don’t advise that you try them all in one night, but we do recommend the mint chocolate chip martini—and trust us, one is enough! Bin 36 (339 N Dearborn; is a cavernous wine bar that also features a wine shop, wine academy, and bistro-style restaurant. The Motel Bar (600 W Chicago Ave.; features classic cocktails (Sidecars, Manhattans, and the Rob Roy) and kitschy decor. When stumbling out of a Cubs game at Wrigley Field, head across the street to the legendary Cubby Bear (1059 W Addison St.;, voted the seventh best sports bar in America by Sports Illustrated. This 30,000-square-foot space features six bars and more than 100 TVs broadcasting every live sporting event imaginable.

Chicago’s other nickname, “Second City,” seems apropos when comparing performing arts scene with that of New York City – but it’s certainly thriving enough to come in a very close second. You can count on a booming theater scene, world-renowned symphony, opera, and dance companies, and free concerts under the stars.

From big Broadway-style musicals to intimate offbeat plays, dozens of great theatrical productions are hitting the floorboards every night. The Loop Theater District is home to several historic theaters of note, including the Chicago Theatre (175 N. State St.;, a beautifully restored 1920s landmark building that appeared in the finale of the movie-musical version of Chicago; the Ford Center for the Performing Arts (aka Oriental Theatre) (24 W. Randolph St.;, built as a movie palace in 1926; and the elegant Cadillac Palace Theater (151 W. Randolph St.;

While the theaters in the Loop District tend to house large-scale Broadway productions, a number of internationally renowned “Off-Loop” theaters are known for exhibiting small high-quality productions. Showcasing new plays, neglected works, and established classics, the Steppenwolf Theatre (1650 N. Halsted St.; has been a pioneering force in Chicago theater since it being co-founded by Gary Sinise in 1974; Sinise, along with longtime ensemble members John Malkovitch, Joan Allen, and John Mahoney, still act in productions today. Located on the Navy Pier, the Chicago Shakespeare Theater (800 E. Grand Ave.; focuses on presenting works by the bard. If you’re looking for a laugh, The Second City (1616 N. Wells St.; is an improv sketch comedy company famous for launching the careers of John Belushi, Bill Murray, Gilda Radner, Chris Farley, and Stephen Colbert.

The League of Chicago Theatres offers half-price, day-of-performance tickets to more than 150 Chicago area venues through its HotTix ( program. Dozens of shows are listed each week, but you must purchase tickets in person at various HotTix locations (Tues–Sat 10am–6pm & Sun 11–4pm; closed Mon): the Loop (72 E. Randolph St.), the Magnificent Mile (WaterWorks Visitor Center, 163 E. Pearson St.), and the North Shore Center for the Performing Arts (9501 Skokie Blvd., Skokie).

The Lyric Opera (20 N. Wacker Dr.;, located in the gloriously renovated art deco Civic Opera House, attracts some of the world’s best singers for its lavish productions. The season runs from September through March. The Chicago Symphony Orchestra (220 S. Michigan Ave.; performs over 200 concerts a year at Symphony Center. The Joffrey Ballet ( performs innovative dance pieces at the Louis Sullivan-designed Auditorium Theatre (50 E. Congress Pkwy.; and various other locations throughout the city.

In the summer months, nothing is more magical than a free concert under the stars with the Chicago skyline as a backdrop. The Grant Park Music Festival ( is a free concert series showcasing the Grant Park Orchestra and Chorus and a variety of ensembles and musicians at Millennium Park’s Jay Pritzker Pavilion (55 N. Michigan Ave.). The ten-week season opens in mid-June and runs through late August.


No matter the limit of your wallet, Chicago boasts a seemingly limitless array of shopping opportunities, from exclusive boutiques and urbane department stores to multi-level shopping malls and funky streetside shops. Best of all for die-hard hunters and gatherers, the city’s premier shopping venues are centrally located and can easily be covered on foot. No wonder it’s called the “City of Big Shoulders” – the bigger the shoulders, the more shopping bags you can carry! Keep in mind that Chicago sales tax is 9% on most purchases.

Easily rivaling Beverly Hills’ Rodeo Drive and New York City’s Fifth Avenue, the fabled Magnificent Mile, the 1.8-mile tree-lined stretch of North Michigan Avenue that extends from the Chicago River to Oak Street near the shore of Lake Michigan, is ground zero for shopaholics. This slice of retail heaven features four vertical shopping malls packed with hundreds of shops and boutiques: Chicago Place (700 N. Michigan Ave.;, an eight-storey emporium anchored by Saks Fifth Avenue; 900 North Michigan Shops (900 N. Michigan;, which includes Bloomingdales and Gucci; Water Tower Place (835 N. Michigan Ave.;, an eight-level atrium above Marshall Field’s department store; and the newest addition, Westfield North Bridge (520 N. Michigan Ave.;, a four-level European-style arcade anchored by Nordstrom. Shop on this glittering stretch and you could be in the company of the glitterati themselves – Gwyneth Paltrow, Mel Gibson, David Schwimmer, Justin Timberlake, and Cameron Diaz have all been spotted here.

Still have a bit of breathing room on the credit card? Just west of the Magnificent Mile, leafy Oak Street is where you’ll find a number of upmarket street-level shops such as Hermes, Prada, and Barneys New York. The old department stores on historic State Street are also well worth a visit, even if your shopping quota has been met and your cards have been maxed out. Marshall Field’s (111 N. State St.; was one of the world’s first (and still greatest) department stores and features a Tiffany glass dome that’s the largest glass mosaic of its kind. The Carson Pirie Scott department store (1 S. State St.;, notable for its ornate iron grillwork and unique blend of form and function, was designed in 1899 by famous local architect Louis Sullivan, one of the pioneers of the modern skyscraper. State Street is also home to the Midwest’s largest jewelry district.

When To Go

Despite its reputation as the “windy city,” Chicago really isn’t any more blustery than other northern cities in the continental United States. The average temperature in Chicago bottoms out at 21 degrees in January and hovers around a very muggy 73 degrees in July. That said, with its endless lineup of cultural events and outdoor activities, summer is certainly the best time to visit, though this is also peak tourist season, so you’ll be dealing with long lines and crowds and higher prices. Certainly, the city’s Stirring Things up in Chicago festival (May 1-October 31; 877-CHICAGO; features an eclectic mix of tours, poetry slams, theater performances, music concerns, cooking classes, unique dining experiences. Come autumn, tourists thin out, students return to school, and the cultural season kicks into high gear, giving the city an electric energy; this is arguably when you’ll get your best bang for your buck. That said, if you’re traveling on a budget, you’ll get the best rates at hotels and cultural attractions in winter – low season. Note that spring is rainy and weather can shift dramatically between warm and cold days.

High season:
May to August

Low season:
December to April

Best bang for your buck:
September to November

Getting There

Due to its central location within the continental United States, getting to Chicago is easy from anywhere in the country. By plane, Los Angeles is four hours away and New York City is only two hours away. Most major domestic carriers offer several daily flights into and out of O’Hare International Airport (, which has the dubious distinction of being one of the busiest airports in the world. O’Hare is the largest hub for United Airlines (, which is headquartered in Chicago, but you’ll also find American Airlines ( using O’Hare as a hub. Several domestic carriers also service the much smaller Midway International Airport (, located about 16 miles southwest of the Loop.

You can of course also arrive in the Windy City by train: Amtrak’s ( national hub is Chicago’s Union Station (210 S Canal St.;, making Chicago the number-one city in the country for passenger-train service. Thirteen train lines converge on the station, including the Lake Shore Limited (service from Boston or New York), the California Zephyr (service from San Francisco), and the Cardinal (service from Washington, D.C.).

Arriving by car is also popular; the main east/west highway is Interstate 90, which merges with Interstate 94 just south of the city and leads directly into town. Interstate 88 and Interstate 80 also come in from the west; the main connection from the southwest is Interstate 55.

O’Hare International Airport is located about 17 miles northwest of the Loop. The El (, the city’s extensive elevated train service, is the fastest and cheapest way to get into the city. From O’Hare, take the Blue Line (every 8mins Mon-Fri 5am-8pm; every 10mins Sat & Sun 5am-11pm; $1.75); the ride takes about 45 minutes. From Midway, take the Orange Line (every 5-7mins; $1.50); it takes about 30 minutes. Taxis, which are easy to find outside at O’Hare, take between 30 and 60 minutes to reach downtown, depending on traffic ($30-$40). The three main taxi lines to remember are American United (773/327-6161) Flash Cab Company (773/878-8500), and Jiffy Cab Company (773/487-9000). If you want to go cheaper than a cab, the best shuttle service is Continental Airport Express (every 10-15mins; $25;, which departs from O’Hare.

Getting around Chicago is easy thanks to its extensive public transit system; the El (short for “elevated train”) is the best way to zip around the city ($1.75; The best places to catch cabs are the Loop, the Magnificent Mile, and in Lincoln Park, otherwise you should call; our preferred companies include Coral Cab (773/488-0122), Checker Cab (773/243-2537), Famous Cab (773/643-4330), Flash Cab (773/561-1444), and Mercury Cab (773/274-3108).

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