Chicago is the home of the blues and the truth of jazz, the heart of comedy and the idea of the skyscraper. Here, the age of railroads found its center, and airplanes followed suit. Butcher of hogs and believer in progress, it is one of the world's great city, and yet the metropolitan luxuries of theater, dining, and shopping have barely put a dent in real Midwestern friendliness. It's a city with a swagger, but without the surliness or even the fake smiles found in other cities of its size.
As the hub of the Midwest, Chicago is easy to find — its picturesque skyline calls across the waters of Lake Michigan, a first impression that soon reveals world-class museums of art and science, miles of sandy beaches, huge parks and public art, and perhaps the finest downtown collection of modern architecture in the world.
With a wealth of iconic sights and neighborhoods to explore, there's enough to fill a visit of days, weeks, or even months without ever seeing the end. Dress warm in the winter, and prepare to cover a lot of ground: the meaning of Chicago is only found in movement, through subways and archaic elevated tracks, in the pride of tired feet and eyes raised once more to the sky.
If you are travelling to Chicago on a budget staying in a Chicago Hostel is a great way to save money and meet new people. Many hostels provide free breakfast, tours of the area and party nights too so they are great fun!
PLACE TO VISIT
Grant Park, 6AM-11PM daily. Right at the center of Chicago, this has been a park space for almost the entire history of the city. Most citywide events and festivals (see below) are held in Grant Park and the Petrillo Bandshell. The centerpiece of the park is Buckingham Fountain (10AM-11PM), which is sometimes accompanied by music and colored lights (8-11PM, May-Sep). There are also tennis courts, softball fields, and a walking trail near the lake. Millennium Park is to the north and the Museum Campus is to the south, so there is a large area to wander. Entrance to the park and most events & festivals is generally free, although some concerts do have an admission charge; in that case, admission to other areas of the park is still free.
Millennium Park, 6AM-11PM daily. Long before it opened, Millennium Park had become notorious for delays and cost-overruns, missing its titular date by a wide margin. However, when it was finished, the biggest shock of all came when it turned out to be quite nice. Aside from plenty of grass and open space, it has modern sculptures in steel and glass, including Chicago's newest must-photo for visitors, The Bean (properly known as Cloud Gate), and the Frank Gehry-designed Pritzker Pavilion for outdoor concerts. Kids will love getting wet in the Crown Fountain (mid-April to the end of summer) at Michigan and Monroe, in which the giant projected faces of Chicago residents spit water into a shallow reflecting pool where everyone is welcome to splash around. Look for tents offering guides to the park near the entrances at Randolph and/or Washington. Free.
Vietnam Veterans Memorial, Designed in coordination with the National Vietnam Veterans Art Museum in the Near South, this waterfront plaza features a timeline from the war, a list of Illinois veterans who were killed in action, and a nice vantage point toward a few iconic buildings down the river. After crossing over the river from the Near North, turn and take the stairs down to the lower level.
Art Institute of Chicago, M-W,F 10:30AM-5:00PM, Th 10:30AM-8PM, Sa-Su 10AM-5PM except Thanksgiving, Christmas, and New Year's Day. One of the premier museums in the US — definitely not to be missed. Famous pieces include "American Gothic" by Grant Wood (the famous stoic farm couple from Iowa), "Nighthawks" by Edward Hopper (the late-night diner), Georges Seurat's pointillist masterpiece "Sunday Afternoon on the Island of La Grande Jatte" and the world's best collection of Impressionist painting outside of France. But there's a lot more to discover, including a great selection of early 20th-century painting, architecture, and photography, and archaeological finds covering 5,000 years of art and cultural history. Admission is $12 adults, $7 children and seniors; free Th 5-8PM.
Bridgehouse & Chicago River Museum, A new, small museum spread over the five floors of the southwest tower of the Michigan Avenue Bridge. Visitors can see displays on the history of Chicago's famously abused river, and also check out the machinery used for raising the bridge. $3 adults, children under 5 are free.
Hancock Observatory, 9AM-11PM. 360-degree view from the 94th floor. Not quite as high as the Sears Tower Skydeck, but with a better view. For drinks, see the Signature Room below. $10.25 adults, $6.50 children, $8 seniors.
Museum of Contemporary Art, T 10AM-8PM, W-Su 10AM-5PM. Contemporary art from around the world. The MCA has a great location and plenty of financial backing, but it's still fighting for recognition in the museum world; while not an upper-tier institution as yet, that has resulted in some interesting exhibitions. There isn't much of a permanent collection, so check what's on before you go. Also, Wolfgang Puck operates a lunch-only eatery in the MCA. $10 ($6 student, free Tuesday after 5PM).
Pritzker Military Library, M-F 8:30AM-4:30PM. A goldmine for people interested in military history, both scholarly and as told by the men and women who lived it, with a vast collection of books, prints, photos, and other military artifacts, and gallery exhibitions. Free evening events with major authors and Medal of Honor recipients are held throughout the year, mostly on Thursday nights; check the schedule on the website. Free
Tribune Tower, Built in 1925, the walls of the Tribune Tower contain rocks from many famous world landmarks, including: the Taj Mahal, the Parthenon, the Great Pyramid, the Cathedral of Notre-Dame, the Great Wall of China, the Berlin Wall, and most recently from the demolished World Trade Center. The Tribune Tower even managed to get its hands on a moon rock, but so far NASA hasn't allowed it to add the rock to the wall.
The Trump Tower, 401 N Wabash Ave. 1362 ft. The Trump Hotel and luxury residential building is both the newest member of the Chicago skyline, completed at the beginning 2009, and the tallest after the Sears Tower — indeed, it is the second tallest in the United States, ninth in the world. The Donald intended for it to be the tallest in the world, but decided to scale back to a mere "second tallest in North America" (after the Sears Tower) following the 9/11 terrorist attacks. The design features three prominent setbacks at the height of nearby buildings: the Wrigley Building, Marina City, and 330 N Wabash, which, combined with its singularly reflective exterior, allow this supertall to blend into the skyline, almost to the point where you could overlook it. As intended, the building reflects and interacts with the Chicago skyline, rather than imposing itself upon it with its great height. Regardless, you will not likely miss this building, and it's plenty interesting to examine — its asymmetric form ensures that you will see something quite different from any different vantage point.
Water Tower, Chicago Ave & Michigan Ave (Chicago Red Line). In 1871, when Mrs. O'Leary's cow kicked over the lantern in her barn — or was framed for the act, depending on who you ask — the Gothic Revival spires of Water Tower were only two years old. Today, along with the Pumping Station on the other side of the street, the Water Tower is the last, dream-like symbol of the Old Chicago that disappeared in the Fire. Surrounded by hotels and colossal department stores, it's also the icon of the new city that arose. At night, the Water Tower is lit from within, and it's a memorable sight. Inside, the vintage machinery is long gone (along with the water), and the plain interior is occasionally used as a gallery space.
The Clarke House Museum, W-Su 12&2PM. Built in 1836, this unassuming little white house is the oldest surviving structure in Chicago. Tours are available through the Glessner House, but it's free to walk around the lovely Women's Park & Gardens that surround it. $10 adults, $9 students/senior, $5 children; add $5 to visit the Glessner House as well. Wednesdays free.
Horner Park, Great big wonderful park with plenty of softball fields, football and soccer fields, basketball and tennis courts, trees, and a nice walking path. The leafy surroundings make it a great place for the annual pumpkin patch in the fall.
Wunders Cemetery, Overshadowed by the magnificent Graceland Cemetery across the street in Uptown, the smaller, slightly overgrown Wunders was established in 1859 and features some intriguing monuments, with more of a forgotten-by-time atmosphere than its more famous neighbor. A third cemetery, Jewish Graceland, is directly south. Free.
The Lincoln Park Zoo and the lakefront are the biggest highlights for a day here, especially with kids, but a few sights, particularly the Biograph Theater and the historic districts, are at their most powerful by night.
Biograph Theater, Plays are shown here, but the theater itself is still best known as the place where John Dillinger went down in 1934. America's most famous bank robber was leaving after a movie with the Lady in Red when FBI agents opened fire. The owners of the theater have never been keen to play up the connection, but the classic marquee is still there. Reportedly, Dillinger fans hold gatherings outside on July 22, the anniversary of his death.
Lincoln Park. The 1.5 mile-long park from which the neighborhood draws its name is dotted with statues of people with ties to Chicago or Germany (like Goethe), and features plenty of paths for running wide-open green space for sports, and even a rowing lagoon to the west.
Lincoln Park Conservatory, 9AM-5PM. Built more than a century ago, the conservatory is right next to the zoo. Even though they're overshadowed by the animals next door, the plants receive an equal amount of care, and there are usually some eye-popping floral displays in the spring. Volunteer-led tours are sometimes available at no cost. Free
Lincoln Park Zoo, Daily 9AM-6PM, winter 9AM-5PM, summer weekends 9AM-7PM. Few things in Chicago are finer than the Lincoln Park Zoo. It's world-class, yet admission is free; its winding, expansive grounds have the charm of age, yet its facilities are modern and the animals are healthy, happy, and personable. The brand new Great Ape House is one to see, and the Farm In The Zoo features plenty for kids to do, but everyone has their own favorites (penguins). Free
Drexel Fountain, at Hyde Park Blvd & Drexel Ave. This ornate fountain that stands in the tiny Drexel Square Park is the oldest in Chicago—indeed, it was one of the first monuments erected in the Chicago area. Commissioned by a wealthy stockbroker by the name of Francis Drexel, who managed to get the avenue, square, and fountain all named after himself without ever setting foot in Chicago
KAMII It looks like a Byzantine style mosque, but that minaret is actually a smokestack for this synagogue. The building was built in 1924 for the reform Isaiah Israel congregation, which later merged with Chicago's oldest Jewish congregation, Kehilath Anshe Ma'ariv (KAM), which in turn moved out of its massive temple on Drexel Avenue. The interior is marvelously elaborate, if you manage to get inside.
The Obama House, 5046 Greenwood Ave (right across the street from KAMII). This pretty house is home to the Obama family of the current President Barack Obama. It's the last house on the right heading south on Greenwood (one-way). The vacant lot to the left was the source of minor controversy in Chicago, when it came out that the Obama family had received it at sub-market rates from friend and criminal real estate broker Tony Rezko. You'll notice, despite the much touted media characterizations of their house as a "Hyde Park white-porticoed mansion," it's not actually in Hyde Park, and while a nice big house, it's no mansion. While they are still living here, though, you're not likely to get anywhere close.
Chicago Bee Building, The home of the Chicago Bee Newspaper, which was founded by Anthony Overton to promote black businesses and issues. The art-deco building has an elegant terra cotta facade and today houses the Chicago Bee Branch Library. Free.
Overton Hygienic Building, 3619-27 State St. Built by the wildly successful African-American entrepreneur Anthony Overton to house the headquarters of his nation-wide cosmetics franchise. The building housed several of his other businesses, including Victory Life Insurance Company and Douglass National Bank, America's first national African-American bank. The building is now owned by the Mid-South Planning and Development Commission. Just across the street from the now demolished, notorious Ida B Wells projects, the formerly beautiful art-deco building is in a sad state of disrepair
Sears Tower, 233 S Wacker Dr. 1451 ft. The Sears Tower remains North America's and, depending on your criteria, the world's tallest skyscraper. It was built for Sears, Roebuck, and Company in 1974 by Bruce Graham of Skidmore, Owings, and Merill. The innovative design successfully handled the challenges of air flow and elevator/emergency support for an unprecedented number of people, but the employees at Sears' formerly collegial suburban campus complained that it handled the challenges too well — they never saw anyone outside their own departments any more! Sears is no longer the building's major tenant, but a number of other, small firms have offices in the building, which also features Chicago's most popular observation deck on the 103rd floor
The Trump Tower, 401 N Wabash Ave. 1362 ft. The Trump Hotel and luxury residential building is both the newest member of the Chicago skyline, completed at the beginning 2009, and the tallest after the Sears Tower—indeed, it is the second tallest in the United States, ninth in the world. The Donald intended for it to be the tallest in the world, but decided to scale back to a mere "second tallest in North America" (after the Sears Tower) following the 9/11 terrorist attacks. The design features three prominent setbacks at the height of nearby buildings: the Wrigley Building, Marina City, and 330 N Wabash, which, combined with its singularly reflective exterior, allow this supertall to blend into the skyline, almost to the point where you could overlook it. As intended, the building reflects and interacts with the Chicago skyline, rather than imposing itself upon it with its great height. Regardless, you will not likely miss this building, and it's plenty interesting to examine—its asymmetric form ensures that you will see something quite different from any different vantage point.
HOW TO REACH
By plane - Chicago is served by two major airports: O'Hare International Airport and Midway Airport. There are plenty of taxis from both to and from the city center, but they are quite expensive, especially during rush hours. Expect upwards of $40 for O'Hare and $30 for Midway. CTA trains provide direct service to both larger airports for $2.25 from anywhere in the city — faster than a taxi during rush hour and a lot less expensive. Many large hotels offer complimentary shuttle vans to one or both airports, or can arrange one for a charge ($15-25) with advance notice.
By bus - Greyhound, 24 hours. America's largest bus carrier offers service to destinations throughout the Midwest. The main terminal is near the southwestern corner of the Loop. There are secondary terminal at the CTA Red Line station at 95th/Dan Ryan and the CTA transit building (5800 N Cumberland). With advance purchase, the trip to Detroit costs about $27.
Megabus, M-Sa 6:30AM-10PM, Su 6:30AM-8PM. Popular in the United Kingdom, Megabus recently established a branch in Chicago. These buses stop in Chicago near Union Station (see below). At present, buses run express from Chicago to eleven other major Midwestern cities. With advance purchase, the trip to Detroit costs about $8.
By train - Chicago is historically the rail hub of the entire United States. Today, Amtrak uses the magisterial Union Station (Canal St and Jackson Blvd) as the hub of its Midwestern routes, making Chicago one of the most convenient U.S. cities to visit by train, serving the majority of the passenger rail company's long-distance routes, with options from virtually every major US city. With its massive main hall, venerable history, and cinematic steps, Union Station is worth a visit even if you're not coming in by train.
By car - Chicagoans have a maddening habit of referring to some expressways by their names, not the numbers used to identify them on the signs you'll see posted on the U.S. interstate highway system, so you'll have to commit both name and number to memory. I-55 (the Stevenson Expressway) will take you directly from St. Louis into downtown Chicago. I-90/94 (The Dan Ryan) comes in from Indiana to the east (via the Chicago Skyway and Bishop Ford Freeway) and from central Illinois (via I-57). I-90 (The Kennedy) comes in from Madison to the northwest. I-94 (the Edens Expressway) comes in from Milwaukee to the north, but recent roadwork has slowed traffic considerably compared to I-90. I-80 will get you to the city from Iowa which neighbors Illinois to the west.
