A Thick Slice of the Windy City: Seth Saith's Chicago Travel Guide

Above graphic and all photos by Seth Arkin. Please do not use without permission.

Having recently turned 44, I have lived in the Chicago area all my life, except for during college—when I was just 50 miles west in DeKalb, IL—and for the first three years of the ‘90s, when I lived in Los Angeles.

I have also had the pleasure of visiting several of the world’s great cities—New York, London, Paris, Rome, Venice, Amsterdam,  Dublin, Madrid, Barcelona, Prague, Montreal, Toronto, Sydney, Melbourne, Stockholm, Copenhagen, Helsinki, Jerusalem, Tel Aviv, Cairo, St. Petersburg, Florence, San Francisco, Boston, Washington and more, some multiple times.

Given these experiences, I feel I can honestly say—without the opinion based too heavily on not knowing any better—that there is nowhere in the world I would rather live (for any longer than a year or so) than Chicago.

And especially for those who value the things I do in a travel destination—art, history, architecture, entertainment, baseball, food—Chicago should be a rather remarkable place to visit.

Keep in mind that Chicago is sprawling (especially with worthwhile attractions beyond the city limits), expensive in terms of downtown lodging and parking, and conceivably a bit challenging for first-time visitors to navigate. It isn’t all that complicated, especially with plenty of public transportation available, but just don’t expect to be able to walk to everything that’s worth seeing.

Depending on where you’re staying, renting a car isn’t essential, but could be helpful in accessing all that Chicago and the region have to offer.

CTA Subway and "L" Map

Similar to how I’ve structured Seth Saith Travel Guides on London, Washington, San Francisco and Detroit, the attractions below are listed in recommended order of what I think any random tourist should see and do in Chicago.

Before I get to the listings--most of which are hyperlinked to more information--here are some links that may be beneficial to those planning a trip to Chicago:

Public Transportation: CTA | Metra Rail
Tours of Chicago: ChicagoTours.us | Chicago Architecture Foundation
Dining & Entertainment Guides: Chicago Reader | Metromix Chicago | Chicago Magazine | Zagat | Dining Guide | GreaseFreak.com | OpenTable
Concert Listings: Pollstar
Festivals: City of Chicago Festivals
Theater in Chicago: TheaterMania | Chicago Tribune / Chris Jones | Chicago-Theater.com
Discount Tickets: HotTix | Goldstar
Chicago Tourism: ChooseChicago.com | ChicagoTraveler.com | WikiTravel
Hotel Guides: Chicago Traveler Hotel Guide | Hotels.com
Chicago Bike Map
Guide to Chicago Beaches
Guide to Downtown Pedway Routes

Keep in mind that no travel guide can be one size fits all; what can most appeal to any traveler varies based on particulars such as age, interests, companions (including kids or not), etc.. So adjust accordingly, but...
This is what I would most want to see and do if I were coming to Chicago for the first time:

1. The Art Institute of Chicago – I’ve been to well over 100 art museums around the world and believe the Art Institute belongs among the Top 5, due to both the breadth and depth of its collection. The Impressionist works—including Seurat’s astonishing Sunday Afternoon on the Island of Grande Jatte—are stunning, but the museum also has an amazing El Greco, a Botticelli, Edward Hopper’s Nighthawks, Grant Wood’s American Gothic and much else.

2. Wrigley Field – I’ve likewise been to 38 other major league baseball stadiums, including all the current ones except the two in Florida, and don’t think any quite compare to Wrigley. Its distinct neighborhood setting, ivy-covered walls, manual scoreboard and the nearly unmatched futility of its occupants, the Chicago Cubs, makes catching a game here unique from all other athletic spectatorship. Of course, you can only do so between April and early October. U.S. Cellular Field, where the White Sox play, is also a comfortable ballpark, if a bit less distinctive.


3. Millennium Park – A relative newcomer to the Chicago landscape, located just north of the Art Institute, Millennium Park features distinctive public works—Pritzker Pavilion and a nearby bridge by Frank Gehry, Cloud Gate (aka “The Bean”) by Anish Kapoor, Crown Fountain by Jaume Plensa, which digitally depicts people’s faces—and has become the city’s best place for communal gathering (including many tourists) and people watching.

4. Chicago-style Pizza – Chicago’s deep dish pizza is every bit as good as it’s purported to be, and considerably better than nationwide replications (such as at the Pizzeria Uno chain). Probably the most emblematic places to get some in Chicago are the original Gino’s East location at 162 E. Superior, the original Pizzaria Uno (29 E. Ohio) or Pizzaria Due (619 N. Wabash), with any Gino’s East, Lou Malnati’s or Pizano’s location also serving up thick-crusted nirvana. 

5. Museum of Science and Industry – I don’t go to Science museums in other cities, because I have one of the best in my hometown. Therefore, I now have scant points of comparison. But MSI has some great exhibits, including a simulated coal mine, live chickens hatching, a large model railroad and an actual German U-Boat. Through February 18, 2013, the MSI has a special exhibition on the Peanuts cartoons called "Charlie Brown and the Great Exhibit."

6. Downtown Architecture Tour – Chicago has, in my estimation, the greatest skyline in the world, but the brilliance of our architecture isn’t always a matter of height, with creations by Louis Sullivan, Daniel Burnham and Mies van der Rohe being just as noteworthy as many of the taller buildings that came later. The Chicago Architecture Foundation offers over 85 different tours by foot, boat, bus, bike and Segway, while Wendella Boats  feature a variety of architecture tours along the Chicago River.

Chicago also has a number of noteworthy sculptures, with impressive works by Picasso, Calder, Miro, Chagall and Dubuffet all within a few blocks in the heart of the Loop (i.e. technically the Central Business District within the “L” tracks that circle it). This Loop Art Tour walking map from WikiTravel provides a pretty good guide.

Graceland Cemetery, near Wrigley Field, has many architecturally and/or sculpturally-significant gravesites of (or by) some the city’s legendary residents (Sullivan, Burnham, van der Rohe, etc.)

7. Frank Lloyd Wright Home & Studio and nearby Wright-designed Homes in Oak Park – The home & studio utilized by America’s greatest architect during his most productive period is in a western suburb, but relatively easy to reach using the Green Line of the “L” (west to Harlem/Lake). Several additional homes designed by Wright are just around the corner on Forest Ave. and otherwise nearby, so get a map at the Home & Studio and do a walking tour as well. Separately, the Robie House, located in Hyde Park near the University of Chicago, is one of Wright’s greatest masterpieces, recently renovated and open for tours Thursday thru Monday.

8. Live Theater – While it doesn’t have the same cluster of long-running shows in large theaters that Broadway and London do, Chicago’s theater scene is nearly as rich as it spreads throughout the region, with professional-level productions being staged in storefronts with as few as 40 seats or so. In addition to Broadway in Chicago touring shows that frequently play downtown--such as the upcoming extended run of The Book of Mormon--top tier troupes include Steppenwolf, Goodman, TimeLine, Lookingglass, Victory Gardens (at the historic Biograph Theatre), Northlight, Drury Lane Oakbrook, Marriott Theatre Lincolnshire and many more. There are also several first-rate Improv venues, including Second City and Improv Olympic, plus the verable Zanies Comedy Club. Discount tickets for many shows are offered through HotTix, Goldstar and often through the theaters themselves.

All photos and graphics by Seth Arkin.
Please reference SethSaith.com if re-posting.

9. Sears (Willis) Tower / John Hancock observation decks – Many observation decks, such as the one atop the Eiffel Tower, can disappoint because the structure you’d most like to see and photograph is the one you’re in. But Skydeck Chicago atop the Willis (formerly and still to most, Sears) Tower and the John Hancock Observatory provide bird’s-eye views of each other and many other Chicago skyscrapers and its beautiful lakefront. I haven’t been to Skydeck Chicago recently enough to “step out on the Ledge,” but having nothing beneath you for 1,353 feet seems pretty cool.

10. The Field Museum – A terrific museum of natural history, featuring dinosaurs—including Sue, a Tyrannosaurus Rex—along with many permanent and special exhibits.

11. The “Tastes” of Chicago – Deep dish pizza merited its own listing (#4) and the annual Taste of Chicago—the world’s largest food festival—is worth visiting if you’re in town in mid-July. But whatever your tastes, they can be well-satisfied. Check out a proper Chicago Dining Guide for a better overview or just explore Chicago’s myriad ethnic neighborhoods and restaurants, from Polish to Puerto Rican, Thai to Jamaican, and on and on. A Chicago-specific favorites include: 1) Vienna hot dogs (available at myriad hot dog stands, including the perpetually chaotic Wiener's Circle. Superdawg is also a unique local institution); Polish sausage (check out Jim’s Original) and specialty sausages at the truly unique Hot Doug’s  2) Italian Beef sandwiches – I like ‘em wet with sweet peppers, from Al’s #1 Italian Beef (the original on Taylor St. or the more convenient one on Ontario, plus several franchise locations), Johnnie’s Beef in Elmwood Park and Arlington Heights or Mr. Beef on Orleans downtown or near Harlem & Irving; 3) Steak, Prime Rib and Baby Back Ribs – We’re home to a lot of great steakhouses; Gibsons and the Chicago Chop House have always done me right; Lawry’s The Prime Rib does its namesake proud and Carson’s still is the place for ribs, though many choices abound; 4) For those who can afford to really splurge, Alinea is perennially ranked as one of the best restaurants in the world (another great one, Charlie Trotter's recently closed). And while I've never been there myself, the Signature Room atop the John Hancock Center can be a treat for those seeking to heighten their dining experience (there is also a Signature lounge a floor up). 5) Although the faux-'50s novelty of Ed Debevic's isn't so novel anymore, it still can be a fun place for those who have never been. And genuinely going back to 1934--at least the original location on the lower level of north Michigan Avenue near the Wrigley Building and Tribune Tower--is the "world famous" Billy Goat Tavern, home of the "Cheezborger, Cheezborger."

12. The Lakefront / Buckingham Fountain / Lincoln & Grant Parks – The “East Side” of Chicago is undoubtedly the city's most beautiful, as it is essentially just Lake Michigan.

Any visit to Chicago should include a walk, jog or bike ride along the lake, with a glimpse of the beautiful Buckingham Fountain in Grant Park and ideally a jaunt through Lincoln Park (the actual park) as well.

13. Water Tower / The Magnificent Mile – In 1871, Mrs. O’Leary’s cow or some udder culprit started the Great Chicago Fire and the Water Tower and the nearby Water Works are all that survived. Water Tower still stands amidst the posh shopping district along North Michigan Avenue known as the Magnificent Mile. It’s a fun place to stroll, shop (if so inclined) and people watch, especially if you like seeing other tourists.

14. Live Music – Chicago is home of the Blues, great Jazz, a pioneering folk scene, a world-renowned Symphony and Opera, one of the premier rock festivals—Lollapalooza—and is a regular tour stop for artists in every genre. I always use Pollstar.com to see who might be playing in town (any town), but Orchestra Hall (home of the Chicago Symphony Orchestra), the Lyric Opera, Buddy Guy’s Legends (Buddy himself does an annual January residency) or Kingston Mines (for blues), the Green Mill and/or Jazz Showcase (for jazz), Old Town School of Folk Music, and Ravinia (an outdoor venue in Highland Park) are among the venues first-time visitors may wish to explore. This City of Chicago site in terms of a variety of festivals put on by the city.

15. Museums / Zoos / Gardens – In addition to the museums listed above, many additional choices exist in Chicagoland in terms of worthwhile places in which to explore and learn. Depending on the proclivities of you, your family or your companion(s), any of these options could fill a good portion of a day: Adler Planetarium; Shedd Aquarium; Chicago History Museum; Lincoln Park Zoo; Brookfield Zoo; Peggy Notebaert Nature Museum / Judy Istock Butterfly Haven; Chicago Botanic Garden; Morton Arboretum; Illinois Holocaust Museum; Museum of Broadcast Communications; National Museum of Mexican Art; Garfield Park Conservatory; the Oriental Institute; Pritzker Military Library; DuSable Museum of African-American History; National Italian-American Sports Hall of Fame; Blues Heaven (in the former Chess Records studio), Newberry Library, Harold Washington Library

The Chicago Cultural Center in the heart of downtown, along Michigan Avenue, was built as the main Chicago Public Library. It now has rotating exhibits, free and often quite good, along with a nice display of architectural photographs. It also provides a handy place to take a break, find a restroom and/or grab coffee in the midst of exploring the Loop and its environs. The Palmer House Hotel on Monroe & State is also worth knowing about for these latter reasons and a splendid ceiling mural.

16. Neighborhoods – I will fail to do justice to the great number of ethnic communities that comprise distinctive neighborhoods throughout the city, but while being wary of your surroundings and security as you venture off the beaten path, you really may want to explore not only such well-known enclaves as Chinatown, Greektown, Pilsen and the Indian area along Devon Ave., but also seek out areas flavored by Polish, Irish, Korean, Vietnamese, Swedish, Jewish, Persian, Puerto Rican, German and myriad other immigrants. A great number of churches dating back a century and which often quite ornate also dot the landscape (St. Mary of the Angels is a cool one). And while it isn’t nearly as extensive as it once was, the Sunday morning Maxwell Street Market (now along Des Plaines Ave.) still serves as a great glimpse into the melting pot that is Chicago. Wikipedia page on Chicago community areas

17. Navy Pier – This is perennially ranked as Chicago’s most popular tourist attraction, but I’m not really sure why. Though not terrifically convenient, it’s a pleasant place to stroll, but doesn’t offer much in the way of things to do. There’s a large Ferris Wheel in homage to the world’s first (built for the 1893 Columbian Exposition), the first-rate Chicago Shakespeare Theatre, an array of restaurants and gift shops and the Smith Museum of Stained Glass Windows, a nice (and free) hidden treasure, but not worth the trip in itself.

18. University of Chicago / Hyde Park / Jackson Park – Chicago is home to some great private universities, with the University of Chicago a particularly distinguished campus in the south side Hyde Park community (where the Obamas reside). Sights include the Rockefeller Chapel, Oriental Museum, Robie House and Nuclear Energy, a sculpture by Henry Moore on the exact site where the world’s first self-sustaining controlled nuclear reaction was conducted. The campus is divided by the Midway Plaisance, which served as the Midway for the Columbian Exposition and is highlighted by Laredo Taft’s Fountain of Time sculpture. The 1893 World’s Fair was principally held in Jackson Park, behind the Museum of Science and Industry (which was the Palace of Fine Arts and only building to survive). A gilded 1/3-size replica of Daniel Chester French’s Statue of the Republic sits in the park, along with a Japanese Garden that was re-created long after the Fair.

19. The North Shore – Heading north from Chicago can bring you to Evanston, home to Northwestern University and a rather cosmopolitan downtown area, then up Sheridan Road to see the Grosse Point Lighthouse, beautiful Baha’i Temple, glorious views of Lake Michigan and glamorous lakefront mansions in such communities as Winnetka, Kenilworth, Glencoe, Highland Park and Lake Forest. If you know where to look, you can see some Frank Lloyd Wright-designed homes (1, 2) and two former military bases turned into residential communities (Fort Sheridan and the Glenview Naval Base, aka The Glen). If you love shopping, Westfield Old Orchard in my hometown of Skokie was one of the country’s first outdoor shopping malls and—long since renovated—one of the most attractive.

20. Catch a Game – While Wrigley Field (#2) offers Chicago’s most unique stadium experience, all of Chicago’s pro teams are much beloved by a devoted fan base. Baseball’s White Sox play at U.S. Cellular Field, the Bears play football within the spaceship that landed in Soldier Field a few years back, the Bulls (basketball) and Blackhawks (hockey) share the United Center—with the popular Michael Jordan statue out front on the East side—and the Fire play non-American football at Toyota Park in Bridgeview. If you like college action, DePaul, Loyola, UIC and Northwestern are Division 1 basketball schools, while the Wildcats of NU also play football up in Evanston.

21. See Some Flicks – Along with first-run cineplexes, Chicago has at least three venues that show art-house/festival-type films on a year-round basis: The Music Box Theatre, Siskel Film Center and Facets Multimedia. Hardcore film buffs might also appreciate the showings at the Portage Theater and Doc Films at the University of Chicago. Out in the Northwest suburb of Park Ridge, the Pickwick is a great old theater that has stood since 1928, with a diner next store said to have been frequented by Park Ridge native Hillary Clinton in her youth. Even further northwest in Barrington, the Catlow is also a cool old movie house with an adjoining sandwich shop from which you can bring in food. If you love old theaters like I do, you may wish to check out the Theatre Historical Society, next to the York Theater in west suburban Elmhurst. I believe they receive visitors on a limited basis.

22. Shoot Some Pix – Within any city I visit, I try to photograph as many of the emblematic sights that I can find. In addition to everything mentioned in the listings above, I’d direct you to these as well:

Marina City (twin “corn cob” apartment buildings), Tribune Tower (and its collection of famous building fragments), Wrigley Building, Merchandise Mart, Chase Tower (First National Bank Building), Aon Center, Chicago Board of Trade Building, Aqua Tower, Trump Tower, Chicago Theatre, “The Marshall Field's Clock” attached to Macy’s (formerly Marshall Field’s) at Randolph & State, the Macy’s holiday windows (Nov-Dec), the Biograph Theatre (where Dillinger was caught & killed), the skyline (from either near the Planetarium or the Roosevelt & Canal area), Union Station, Michigan Avenue Bridge, Prairie Avenue Historic District, Clarke House (oldest Chicago home), the Auditorium, Uptown Theatre (exterior only), IIT campus (largely designed by Mies van der Rohe and other prominent architects), The Drake Hotel, Holy Name Cathedral, Leaning Tower of Niles. 

23. Make the Kids Happy - I've never been to American Girl Place, now located within the Water Tower Place high-rise mall on Michigan Ave., but I'm aware that it's extremely popular with young girls. Similarly, it's been at least a couple of decades since I visited Six Flags Great America in far north suburban Gurnee, but for those who love amusement parks--and particularly those with several roller coasters--it might well be worth the trip.

Hopefully, this gives someone considering coming to Chicago for the first time--or who has been here several times--a good starting point for places to consider seeing. While I think Chicago makes a fantastic place to visit, I had some thoughts on our soft spots as a tourism city and shared some suggestions about potential new attractions in this article, which began as an introduction to this one.

Please let me know if you need any specific guidance or have thoughts on great sights I failed to cite.

Chicago looks forward to your visit. Welcome, and happy travels.