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Chicago City Guide

Suggested Itineraries for Visiting Chicago

©2006 Chicago Convention and Tourism Bureau From the John Hancock Observatory, you get a great view of Chicago and the Lake Michigan shoreline.

We've told you about all the things to do in Chicago. But how will you fit them all into your trip? We've created these suggested itineraries that will help you hit on the highlights in your areas of interest -- including special events and attractions, arts and culture, architecture and landmarks, shopping, nightlife and entertainment, and relaxing and unwinding.

1-, 2-, and 3-Day Suggested Itineraries for Special Events & Attractions in Chicago

1-, 2-, and 3-Day Suggested Itineraries for Special Events & Attractions in Chicago


What visit to Chicago is complete without a trip to the Sears Tower? Or Wrigley Field? Here are some suggested itineraries that will ensure that you get to the must-see attractions in Chicago:

1 day: If you've only got one day to see Chicago, you'll want to concentrate on the major downtown sites. You can't beat the Art Institute of Chicago (111 S Michigan Ave) for its impressive collection of art, from Renaissance Italian to French Impressionism to modern American. And it's not just for art snobs: The museum caters to families with a wide array of hands-on activities. If you go on a Tuesday, note that while admission is free, this draws large crowds.

When you're ready for some fresh air, head one block north to Millennium Park (east of Michigan Avenue, between Randolph and Monroe), where you can admire architect Frank Gehry's signature ribbons of steel above the Pritzker Music Pavilion and see the skyline brilliantly reflected in sculptor Anish Kapoor's Cloud Gate (known locally as "The Bean," for its distinctive kidney-bean shape).

At some point, you'll want to admire the city from one of its highest vantage points: either the Sears Tower Skydeck (233 S Wacker Dr) or the John Hancock Observatory (875 N Michigan Ave). Although the Sears Tower is the most famous, views from the Hancock are just as good, and it's located near more shops and restaurants.

Weather permitting, you can get active by renting a bike at the park for a jaunt along the lakefront, or simply walk along the waterfront (pausing for photo ops, of course). From the Shedd Aquarium, Shoreline Marine Company runs 30-minute boat tours to Navy Pier. The boats are a perfect way to see a new perspective on the city.

2 days: Start your day at the Museum Campus, where the Shedd Aquarium (1200 S Lake Shore Drive) and the Field Museum of Natural History (1400 S Lake Shore Dr) are within walking distance of each other. At the Shedd, you'll want to catch a show at the Oceanarium, where huge floor-to-ceiling windows overlooking the lake make you feel like you're sitting outside. Must-see exhibits at the Field Museum of Natural History include Sue, the largest T. rex skeleton ever found, and the Man Eaters of Tsavo, a pair of lions who terrorized British railroad workers in East Africa in the late 1800s.

Spend the rest of your time on a Michigan Avenue stroll. Stop at the Michigan Avenue Bridge (at the Chicago River between Michigan and Wabash) for excellent skyline photos, then swing by the Chicago Tribune Tower (435 N Michigan Ave) and check out the mismatched stones embedded in its walls. They're all pieces of world-famous buildings, from the Parthenon to the Alamo.

©2006 Chicago Convention and Tourism Bureau The Ferris wheel on Chicago's Navy Pier is 150 feet high.

Then join the throngs of mostly suburbanites and tourists at Navy Pier (600 E Grand Ave), an old naval station renovated in the 1990s that has become an urban playground offering rides, stores, museums, and a movie theater. Its most visible attraction is a 150-foot Ferris wheel, which offers an attractive view of the lake and skyline. You can also watch a movie at the IMAX theater, tour a stained-glass museum or children's museum, or window shop at the dozens of stores ranging from specialty boutiques to kiosks. You can also listen to a free outdoor concert or grab a one-hour cruise from the pier. On Saturday night at 10 pm, you can watch a fireworks show, with synchronized music, lit from a boat on the lake.

3 days: Head north to Lincoln Park (2400 N Stockton Dr). Start your day at the Lincoln Park Zoo (2200 N Cannon Dr), making sure to stop at the Regenstein Center for African Apes and the African Journey exhibit (which recreates various African ecosystems, from dusty desert to humid jungle). Stroll east along Fullerton Avenue when you're ready for a break; you can either chill out on the shady grass, taking in the tranquil lakefront view, or dip your toes into the frigid Lake Michigan water at the northern edge of North Avenue Beach.

Later, get some background on what made the city great at the Chicago History Museum (1601 N Clark St), where interactive exhibits arranged by theme take both adults and children through the city's fascinating past. You can also learn the real story behind the Great Chicago Fire. End up with a walk along Wells Street in Old Town or Armitage Avenue further west, both vibrant neighborhoods with lots of restaurants and fun shops for browsing. One good restaurant to try is Mobil Two-Star Sushi Samba Rio (504 N.Wells St), which serves a wild fusion menu of Japanese and Brazilian dishes, like chicken teriyaki with Peruvian mashed potatoes, and cocktails to match. Or you can stop in at Mobil Two-Star Tizi Melloul (531 N Wells St), which serves coriander-roasted duck or grilled octopus as part of its Mediterranean menu. If you stop in on Sunday evening, you can watch a belly dancing show with your meal.

1-, 2-, and 3-Day Suggested Itineraries for Arts & Culture in Chicago

1-, 2-, and 3-Day Suggested Itineraries for Arts & Culture in Chicago

With its fine arts and fine performances, Chicago has plenty to keep you busy during your stay. Here are some suggested itineraries for those who want to see the best of Chicago's arts and culture:

1 day: Begin at the Art Institute of Chicago (111 S Michigan Ave), where you could easily spend a day admiring the wide range of works, from medieval to modern. The museum's gift shop is a good place to pick up gifts for culture-vulture friends.

©2006 Paul Goyette Visitors to Chicago find this unnamed Picasso sculpture (known as "The Picasso") in front of the Richard J. Daley Center and Plaza.

After stopping to admire the public art in Millennium Park (Michigan Ave and Randolph St), including the Crown Fountain and the bean-shaped "Cloud Gate" sculpture, stop by the Chicago Cultural Center (78 E Washington St), a gorgeous Beaux-Arts mansion that was once the city's public library. The Tiffany dome on the upper floor is said to be the largest in the world. While you're there, pick up a copy of the "Loop Sculpture Guide", a booklet that maps out the city's collection of public art.

Then, stroll through The Loop to admire the sculptures that dot the downtown business district. An untitled work by Picasso (called simply "The Picasso" by locals) sits in the Richard J. Daley Center and Plaza (50 W Washington Blvd), and Miro's Chicago, a 39-foot-tall steel, wire mesh, concrete, bronze, and ceramic tile sculpture, can be found on Washington Street only a few blocks away. The Four Seasons, a 3,000-square-foot mosaic designed by Marc Chagall, stands at First National Plaza (Monroe and Dearborn Sts).

2 days: Start the day at the Museum of Contemporary Art (220 E Chicago Ave), a building that looks like an uninviting fortress from the outside, but is filled with light and open space once you get inside. Look for pieces from the Chicago Imagists, a local art movement from the 1960s, as well as national touring shows. If you time it right, you can catch the free tour offered at 1 pm daily except Mondays (tours are given more often on weekends); admission to the museum is free on Tuesdays.

Then you should head to the River North Gallery District (loosely bordered by the Chicago River, Orleans Street, Chicago Avenue, and State Street), which features galleries specializing in contemporary glasswork, sculpture from Latin America and Africa, experimental photography and pretty much everything in between. The neighborhood is also home to a number of contemporary furniture and home-decor showrooms; you'll find an especially creative, intriguing mix at Orange Skin (223 W Erie St).

3 days: Chicago is known for its vibrant theater scene, and you can't leave town without catching at least one show. Research your options before you arrive through the League of Chicago Theatres Web site, or start the day at Hot Tix, a ticket service that sells same-day theater tickets for half price (offices are located at the Water Works Visitor's Center, 163 E Pearson St, and in The Loop at 72 E Randolph St).

For a glimpse at an off-the-beaten-path art scene, stop by Intuit: The Center for Intuitive and Outsider Art (756 N Milwaukee Ave). Chicago has a number of well-known collectors of so-called "outsider art," produced by independent-minded artists with no formal training or ties to the professional art world. (Note: Intuit is only open Wednesday through Saturday). Then check out some of the newest art galleries in the West Loop.

The Douglas Dawson Gallery (400 N Morgan St), specializing in African and Asian art, and the Donald Young Gallery (933 W Washington St) are two of the most impressive spaces.

Spend the evening at the concert or play of your choice. If you're here in the fall, winter, or spring, you can catch a performance by the world-renowned Chicago Symphony Orchestra (220 S Michigan Ave). In the summer, the Grant Park Symphony and Chorus gives free concerts in Millennium Park (Michigan Ave and Randolph St).

1-, 2-, and 3-Day Suggested Itineraries for Architecture & Landmarks in Chicago

1-, 2-, and 3-Day Suggested Itineraries for Architecture & Landmarks in Chicago

Chicago is the home of the skyscraper. In this city of architectural innovation, you'll find buildings by designers as wildly different as Frank Lloyd Wright and Frank Gehry. Follow these suggested itineraries for viewing Chicago's architecture and landmarks.

1 day: Spend the morning taking the Chicago Architecture Foundation's Historic Skyscrapers Tour, which will give you an overview of why the city's architecture was so revolutionary. Among the landmarks you'll visit: the massive, hulking Auditorium Theatre building (430 S Michigan Ave), the Reliance Building (now the Hotel Burnham at 1 W Washington St), and the Monadnock Building (53 W Jackson Blvd), where you can see the 6-foot-thick walls that were necessary to support the tower's 17 stories.

Mobil Two-Star Atwood Cafe, inside the Hotel Burnham (1 W Washington St) makes a good stop for lunch; the elegant, velvet-curtained dining room makes you feel like you've stepped back in time, although the menu gives traditional American comfort foods a modern twist. The chef got her start as a pastry cook, so save room for dessert, such as the lusciously decadent white chocolate-banana bread pudding.

In the afternoon, get a bird's-eye view of the city by visiting the Sears Tower Skydeck (233 S Wacker Dr). Afterward, stroll over to Millennium Park (east of Michigan Avenue, between Randolph and Monroe Sts) to admire the Pritzker Music Pavilion, topped by massive curved ribbons of steel designed by Frank Gehry. He also designed the adjacent serpentine bridge over Columbus Avenue.

2 days: Spend most of the day exploring the South Side neighborhood of Hyde Park, home to the University of Chicago. The university's campus, where Gothic stone buildings surround wide grassy quads, recalls the classic look of Oxford and Cambridge. Hyde Park is also the site of Robie House (5757 S Woodlawn Ave), one of Frank Lloyd Wright's most significant residential buildings, especially notable for its stained-glass door and windows. Visits are by guided tour only, which are scheduled daily between 11 am and 3 pm.

Finish up the day with a drink at the Signature Lounge on the 96th floor of the John Hancock Center (875 N Michigan Ave). Sure, the cocktails are overpriced, but you're really paying for the view, which is especially impressive as the sun sets and the city lights start to sparkle.

©2006 Michael Clesle In Oak Park, just west of Chicago, you can visit the Frank Lloyd Wright Home and Studio. Guided tours of the home give a good overview of Wright's life and of his historical significance.

3 days: Follow the footsteps of Frank Lloyd Wright with a day trip to Oak Park (you can catch the Green Line L train from downtown west to Harlem Avenue, or sign up for a bus tour run by the Chicago Architecture Foundation). Start your visit at the Frank Lloyd Wright Home and Studio (951 Chicago Ave), where the guided tours give a good overview of Wright's life and historical significance.

Afterward, stock up on architecture-related gifts and souvenirs at the Gingko Tree Bookshop next door (951 Chicago Ave, Oak Park), then break for lunch or a sundae at Peterson's (1100 Chicago Ave), a restaurant and ice-cream parlor that's been in business since 1919. The turtle sundae, topped with chocolate, caramel and roasted pecans, is a popular house specialty.

In the afternoon, visit Oak Park's Unity Temple (875 Lake St), another Wright landmark. The interior's cube-like design was a radical departure from traditional church architecture, and today it's acknowledged as an important milestone in the development of modern architecture.

1-, 2-, and 3-Day Suggested Itineraries for Shopping in Chicago

Shopping in Chicago ranges from upscale and expensive to unusual and off-the-wall. If you follow these suggested itineraries, you'll get to all of the shopping hotspots.

1 day: Yes, it's touristy, and yes, it's crowded, but you can't come to Chicago and not window-shop along Michigan Avenue. Whether you're coveting designer duds at Chanel and Giorgio Armani -- or picking up cheap knockoffs of designer looks at H&M -- Michigan Avenue has the most concentrated number of shops in the city, including the Apple Store -- pick up the newest iPod or accessories for your Mac.

If you're traveling here with a girl younger than 12, it's pretty much mandatory to take a detour to American Girl Place (111 E Chicago Ave), where dolls even get their own seats at the in-store cafe.

When you're ready for a break, head up to the 6th floor of the 900 North Michigan Avenue Shops high-rise mall, where cozy Oak Tree offers an eclectic menu of lunch items (everything from fajitas to omelets) at reasonable prices. If you're lucky, you can snag a table overlooking the Michigan Avenue throngs.

Macy's (111 N State St) is a block-long Loop flagship store worth a visit. The grand central atrium -- topped by a gorgeous Tiffany mosaic dome -- recalls the days when shopping downtown was a special occasion. One small reminder of the building's former owner -- Marshall Field's -- remains: the store's signature dark-green boxes of Frango Mints. The creamy mix of chocolate and mint makes these a great gift, but make sure to buy at least one box for yourself!

2 days: For a glimpse of upscale-but-not-stuffy Lincoln Park shopping, head north to Armitage Avenue. The shops here appeal to the neighborhood's mix of single professionals and well-off young families. Lori's Designer Shoes (824 W Armitage Ave) offers big-name footwear at substantially discounted prices; it's a regular stop for local fashionistas, despite the rather ramshackle interior, strewn with half-opened shoeboxes.

At 1154 Lill (904 W Armitage Ave), you can design your own purse or tote bag using the store's vast selection of fun fabrics (although bags take a few weeks to make, they can be shipped to your home after you leave town). If you like to discover unexpected treasures, don't miss Art Effect (934 W Armitage Ave), which stocks a wonderfully eclectic mix of clothing, housewares, jewelry, and gift items.

When you're ready to devour some good food, stop at Tartino's (1112 W Armitage Ave) for contemporary American and Italian inspired cuisine, like farfalle with smoked chicken, tomatoes, and spinach or duck breast with roasted butternut squash and lentils. You can even people-watch by enjoying your food at a table in the restaurant's sidewalk garden.

3 days: To see where Chicago's top style-setters shop, spend the day in the Bucktown and Wicker Park areas, with a mix of designer stores and hip clothing boutiques. For the really fashion forward, p.45 (1643 N Damen Ave) is the top spot to discover little-known designers (be forewarned, though: sizes here tend toward the small). If you like your clothes pretty rather than edgy, Tangerine (1719 N Damen Ave) and Jolie Joli (1623 N Damen Ave) stock outfits eminently wearable (if a tad expensive).

For clothing with a sense of humor, don't miss The T-Shirt Deli (1739 N Damen Ave), where you can "order" a custom T-shirt by browsing through thick notebooks of vintage decals (your completed T-shirt is then wrapped in a brown paper bag with a bag of potato chips, deli-style). For one-of-a-kind, cleverly designed gift items, Stitch (1723 N Damen Ave) is a favorite of local designers and stylists.

1-, 2-, and 3-Day Suggested Itineraries for Nightlife & Entertainment in Chicago

1-, 2-, and 3-Day Suggested Itineraries for Nightlife & Entertainment in Chicago

From blues joints and ritzy clubs to the Chicago Symphony and the old ballpark, Chicago has something for everyone. Here are some ways to organize your entertainment options:

1 day: If you're here in the summer, there is no more quintessential Chicago experience than a Chicago Cubs baseball game at historic Wrigley Field (1060 W Addison St). Most games tend to sell out in advance, but if you show up early, you can usually find someone trying to sell off their tickets out front. Head for the bleachers if you want loud and rowdy; the rest of the park is relatively restrained (as long as you root for the Cubbies).

After the game, grab a drink and relive the game's highlights at the traditional neighborhood tap of John Barleycorn's (3524 N Clark St) or Cubby Bear (1059 W Addison St), where many fans go for live music, watch sports, or eat at the Cubby Cafe. For a complete change of pace, you could also stop by The Holiday Club (4000 N Sheridan Rd) for swinging jukebox music with a martini or beer and rich comfort foods like meatloaf and mashed potatoes.

©2006 Blank Campbell The Green Mill, in Chicago's Uptown neighborhood, is a great place to hear topnotch local jazz acts.

In the evening, hang out at one of the city's historic music clubs, the Green Mill (4802 N Broadway), in the North Side neighborhood of Uptown. The nightly jazz lineup features top-notch local talent, but the real draw is its vintage look; in the 1920s, it was a speakeasy frequented by Al Capone.

2 days: Catch a matinee at one of Chicago's independent movie theaters. The Gene Siskel Film Center (164 N State St), located in the heart of The Loop, is a modern screening room that shows international films in monthly themed series. The Music Box Theatre (3733 N Southport Ave) is a vintage gem where twinkling "stars" sparkle on the ceiling and faux Italianate building facades surround the seats. Shows include a mix of independent films and re-released classics.

At night, pick from among the many concerts in town, whether it's blues at Buddy Guy's Legends (754 S Wabash Ave), the latest up-and-coming rock band at Metro (3730 N Clark St) or a singer-songwriter at intimate Schubas Tavern (3159 N Southport Ave).

3 days: Begin the day with lunch at Goose Island Brewery (1800 N Clybourn Ave), home of the city's best hometown brew. Sure, you can get a taste of Goose Island's beers that change each season, but the food is also surprisingly good. And, during the day, the dining room is also kid-friendly, with groups of local families catching up over drinks and the restaurant's addictive homemade soft pretzels. The burger topped with Stilton cheese is hearty and satisfying -- the perfect accompaniment to a cool pint of Goose Island ale.

In the afternoon, let loose with a few rounds at 10pin (330 N State St), a retro-cool bowling alley with a menu of cool cocktails and upscale snacks.

Round off the day with dinner at Mobil's Three-Star Gibson's Steakhouse (1028 N Rush St), where the people-watching is as much a part of the experience as the monstrous steaks and super-size martinis. Cap things off with drinks and dancing at Le Passage (1 Oak Place), the reigning late-night hangout for the city's beautiful people.

1-, 2-, and 3-Day Suggested Itineraries for Relaxing & Unwinding in Chicago

1-, 2-, and 3-Day Suggested Itineraries for Relaxing & Unwinding in Chicago

Where better to kick back and take it easy than in a town with so many parks, beaches, and gardens? These suggested itineraries will help you relax and unwind while visiting Chicago.

1 day: Begin the day with an architectural river cruise offered by the Chicago Architecture Foundation (224 S Michigan Ave) or Shoreline Marine Company (474 N Lake Shore Dr). Sailing past the city's majestic buildings is the perfect way to explore the city without getting tired out. Lunch at Le Colonial (937 N Rush St), a Vietnamese restaurant that invokes the style of 1920s Saigon; the overall feel is cozy, secluded, and unrushed. The shrimp grilled on sugar cane skewers is good, and so is the filet mignon diced into small pieces and stir-fried with yams and green beans.

Spend the rest of the day doing as the locals do: reading a book or newspaper or simply dozing near the lakefront. Avoid crowded Oak Street Beach and head instead for the tranquil area along Cannon Drive just north of Fullerton Avenue. This semi-wooded, lush park area will truly make you feel you've left the city behind. You can finish up the day with dinner at one of the city's finest restaurants, Mobil Three-Star North Pond Restaurant (2610 N Cannon Dr), which is tucked into a former warming hut for ice skaters. The upscale American menu focuses on creative combinations of impeccably fresh local ingredients, such as honey-glazed pork chops or horseradish-crusted strip steak.

2 days: Enjoy the outdoors while staying just slightly active with low-key outdoor activities. In Lincoln Park, the Diversey Driving Range (141 W Diversey Pkwy.) is an affordably priced driving range where you'll be surrounded by a mix of low-handicap experts and complete beginners (so don't worry if your game isn't exactly Tiger Woods-worthy). Downtown, the Green at Grant Park (352 E Monroe St) is an 18-hole putting course steps from the lake, where you can practice your short game in a low-pressure setting. If you're in town during the winter, the nearby McCormick Tribune Ice Rink in Millennium Park (Michigan Avenue and Randolph St) offers a quintessential cold-weather experience: bundled-up, red-cheeked skaters gliding past the downtown skyline.

Recover from all that not-so-hard work with a pampering session at Kiva (196 E Pearson St), an extensive spa in the Water Tower shopping center. Whatever your preference -- an age-defying facial, hot stone therapy, or a simple massage -- you'll find it at this tranquil oasis, which somehow manages to block out the bustling city outside.

3 days: Spend the day at Navy Pier (600 E Grand Ave), a visitor-friendly destination that offers something for the whole family. Start with a ride on the 150-foot Ferris wheel, where you'll get panoramic views over the whole city. If you're traveling with kids, you'll want to stop by the nearby carousel, or try the 18-hole miniature golf course (each hole has a Chicago theme).

Then, escape the crowds by taking off for a ride on The Windy, a four-mastered schooner that takes visitors on 90-minute lake cruises. Finish up your Navy Pier visit with a walk to the very end of the pier, from where you'll enjoy photo-worthy views of the skyline.

At night, indulge yourself by splurging at one of the city's finest restaurants, where the trade-off for sky-high prices is impeccable service, award-winning food, and a meal that can linger on for hours. Mobil's Three-Star Spiaggia (980 N Michigan Ave), considered one of the best Italian restaurants in the country, looks out over Oak Street Beach from its second-floor windows. The prix-fixe menus will introduce you to an Italian cuisine far beyond spaghetti and meatballs (if you have a chance to try the truffle risotto, grab it).

Another special-occasion dining spot is Mobil's Four-Star Everest (440 S LaSalle St), perched on the 40th floor of a Loop office building. This French restaurant, specializing in dishes from chef Jean Joho's native Alsace, features stunning views across the city, along with elegant, beautifully prepared food.

Whether you call it the Windy City, the City with Big Shoulders or the Second City, Chicago is brimming with things to see and do. Visitors to the city will find no shortage of attractions and diversions, from fine arts at the Art Institute of Chicago to a baseball game at Wrigley Field. Chicago might be the city that works, but it knows how to play hard, too. Once you visit Chicago, you'll be calling it your kind of town.

© Publications International, Ltd.


Chicago-based writer and editor Elizabeth Blackwell is the author of Frommer's Chicago Guidebook, as well as The Irreverent Guide to Chicago and Memorable Walks in Chicago. She also contributes regularly to publications such as The Wall Street Journal and Chicago Magazine.

Related Links

Art Institute of Chicago

The Auditorium Theatre

Center for Intuitive and Outsider Art

Chicago Architecture Foundation

Chicago Botanic Garden

Chicago History Museum

Chicago Loop Synagogue

Chicago Symphony Orchestra

Chicago Temple


Field Museum of Natural History

Frank Lloyd Wright Home and Studio

Gene Siskel Film Center

Goodman Theatre

Harris Theater for Music and Dance

Hot Tix

Lookingglass Theater

Lyric Opera of Chicago

Mayor's Office of Special Events

Millennium Park

Museum of Contemporary Art

Robie House

Shedd Aquarium

Steppenwolf Theatre Company

Unity Temple