→ You’re ready to start building your stamina with a high-intensity activity: a summer art fair. But fest season’s sweaty masses and preschoolish paintings fill you with dread. One exception? The Midwest’s oldest juried lineup, the 57TH STREET ART FAIR, runs 6/5-6 in Hyde Park and features artwork you can actually picture hanging over your couch. Need help picking out a piece? Sign up for a free art-buying boot camp at 57thstreetartfair.org.

→ Don’t forget conditioning—and plenty of bottled water. Last year at Pitchfork, you passed out on a beach towel with a lukewarm PBR in hand. This year you plan a test run. DOWNTOWN SOUND, Millennium Park’s summer-long nod to pop music, doesn’t cost a dime, and the lineup rocks: She & Him, a.k.a. the film ingénue Zooey Deschanel and the alt-folkie M. Ward, plays 6/7; Chicago’s favorite rapping sibling, Kid Sister (right), headlines 7/19.

→ Emboldened by your newfound vigor, you step up the pace with world beats. MUSIC WITHOUT BORDERS, also free in Millennium Park, returns with a stellar schedule, including a centennial ode to the onetime Illinoisan Howlin’ Wolf, with Otis Taylor (left) and others on 6/10.

→ Need to dial back the pace? Think of the PRINTERS ROW LIT FEST (6/12-13) as your workout cooldown: blocks of books to browse, author lectures to catch (including Nickel and Dimed’s Barbara Ehrenreich, Bird by Bird’s Anne Lamott, and Chicago’s own crime queen Sara Paretsky)—or not, pending your speed.

→ You’re finding your groove, but you’ve come to a crossroads: On 6/17, do you . . .

BUST A MOVE
If you want to take notes, then names, see HUBBARD STREET DANCE CHICAGO perform free throughout the Art Institute, then practice your own foot-work a few blocks down at the launch of this year’s CHICAGO SUMMERDANCE, a local favorite featuring free lessons and dancing under the stars.

OR

BUST A GUT
Want to give the cardio a break? Work your abs at the JUST FOR LAUGHS comedy fest (6/15-19). Aziz Ansari and Ellen DeGeneres sold out in nanoseconds, but you still have a shot at Bob Odenkirk’s kid-friendly The Not Inappropriate Show (6/18-19).

For more pint-sized fun, see Summer Hot List: Family Fun »

→ When the temperature rises, Chicago theatre goes experimental—sort of like that time you got hooked on Bikram yoga. Feeling daring, you consider three avant-garde options:

1. The script for CHERRYWOOD, opening 6/17 at Mary-Arrchie Theatre Co., contains lines that cast members choose at random—which would sound like a recipe for cherry-flavored disaster if it weren’t for the Obie-winning David Cromer (Our Town) at the helm.
2. The highly unconventional Dog & Pony Theatre Co. has tackled Henry Darger (As Told by the Vivian Girls) and beat-poetry verse (God’s Ear); now the troupe takes on that pinnacle of sinister surreality, the postal system, in DEAD LETTER OFFICE (6/9-18).
3. Collaboraction’s tenth annual festival of new plays, SKETCHBOOK (6/10-27), includes world premieres by The Hypocrites’ love-him-or-hate-him-but-at-least-you’ve-heard-of-him artistic director, Sean Graney, and Brett C. Leonard (whose last Chicago premiere, The Long Red Road, scored Philip Seymour Hoffman as director).

→ You overdid it: Too much theatre gives you a muscle spasm. Must find a source of intellectual potassium. Solution? RAVINIA, featuring a lineup of births, deaths, and, OK, Jethro Tull (6/20):

• Bring a cupcake for Chopin’s 200th when the pianist Garrick Ohlsson plays 6/28.
• Whistle a dirge for the 20th anniversary of Bernstein’s and Copland’s deaths (7/11).
• Raise a plastic champagne flute to Schumann’s 200th with the pianist Christoph Eschenbach, who turned 70 this year (7/24).
• For lower potassium but more zest: Catch Steve Martin on 6/12 or The Swell Season on 7/14.

→ Keep stretching your classical muscles every Tuesday with a free RUSH HOUR CONCERT at St. James Cathedral. Then hop, skip, and bebop over to TUESDAYS ON THE TERRACE, where local jazz bigwigs (the Velvet Lounge honcho Fred Anderson on 6/29 and 8/24; Chicago’s jazz heir apparent Maggie Brown on 7/6) serenade listeners free in the Museum of Contemporary Art’s backyard.

→ Exhausted by all of summer’s moving parts, you need a minute to relax. Ducking inside the MCA, you spy ALEXANDER CALDER AND CONTEMPORARY ART: FORM, BALANCE, JOY, a collection of kinetic sculptures by Calder (right), plus others indebted to the master. Sit, space out, and let the slowly rotating mobiles help you unwind (6/26-10/17).

→ Your respite is short lived. Steppenwolf is premiering A PARALLELOGRAM, written by the Tony winner Bruce Norris (The Pain and the Itch), directed by the Tony winner Anna D. Shapiro (August: Osage County), and costarring the Jeff winner Tom Irwin (7/1-8/29). Do you want to go? Of course you do.

→ Just in time for July 4th, you get a second wind when you realize your summer of culture isn’t only about you; it’s about celebrating where you live. Reinvigorated, you head to FitzGerald’s AMERICAN MUSIC FESTIVAL (7/1-4). The area’s best red-white-and-blues tribute offers four days of made-in-the-USA boogie, featuring the pianist Marcia Ball. If you’re feeling especially frisky, sign on for round 2: Old Town School of Folk Music’s FOLK & ROOTS FESTIVAL (7/10-11).

→ You’ve hit summer’s halfway point. Time to take a break and take stock: While the fourth annual CHICAGO DANCING FESTIVAL doesn’t kick off until 8/26, tickets to the fest’s three free days of world-class performances will be released 7/16—and last year seats went in two hours flat. Cultural-maven-in-training that you are, you keep one eye peeled on chicagodancingfestival.com for details.

→ It’s time to put your stamina to the test at PITCHFORK. There’s no messing around on 7/18 when the indie gods Pavement, the beguiling multi-instrumentalist St. Vincent, and the crooner Cass McCombs all compete for your attention—and the timing of your bathroom breaks.

→ You manage to stay the course at Pitchfork, but a touch of heat exhaustion sends you in search of some A/C.

• OPTION 1: a major Chicago premiere. Piven Theatre stages LATE: A COWBOY SONG, by the MacArthur fellow and Wilmette native Sarah Ruhl, with Ruhl’s muse and the Piven alum Polly Noonan starring (7/17-8/22).
• OPTION 2: a master retrospective. HENRI CARTIER-BRESSON: THE MODERN CENTURY (above), at the Art Institute, features some 300 decisive moments—the first in-depth look at the artist in 30-plus years (7/24-10/3).

→ Stumped, you pause for reflection. Remember when you sold your treadmill so you could hear the bass-baritone John Relyea at the Lyric and the violinist Christian Tetzlaff at the Chicago Symphony Orchestra? Determined never to be poor again, you decide to brave the great outdoors and hear Relyea (7/23-24)—free!—as part of the GRANT PARK MUSIC FESTIVAL before returning on 8/4 for Tetzlaff. Then shake it like a Polaroid picture when the Portland Cello Project plays inventive covers of songs such as Outkast’s “Hey Ya” (8/2) as part of the series DUSK VARIATIONS.

→ It’s what you’ve been training for: LOLLAPALOOZA takes over Grant Park 8/6-8. But with so many acts on offer, will you hear Lady Gaga (right) or Green Day? MGMT or Empire of the Sun? The National or The New Pornographers? Choose wisely.

→ With Lolla down, you’re primed for a Labor Day victory lap: The JAZZ CLUB TOUR, a trolley circuit of jazz venues citywide (9/1), segues into summer’s official finish line, the CHICAGO JAZZ FESTIVAL (9/4-5).

CLICK HERE FOR MORE DETAILS ON ALL OF THE EVENTS »

Photography: (Kid Sister) Don Flood, (Taylor) Stacy Moore  Opposite: (Calder) Alexander Calder, Mobile, 1948. Collection Walker Art Center, Minneapolis. © 2010 Calder Foundation, New York/Artists Rights Society, New York, (Lady Gaga) Solarpix/PR Photos