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Hot Times in the City

Looking to make the most out of this summer? Consider your wish granted. These itineraries will get you the best seats at the area’s top summer offerings—and you’ll arrive in style.

Join over 200,000 attendees for three days of music in historic Grant Park.

Steppenwolf’s Grand Concourse, July 2-Aug. 30
A big hit in NYC, Grand Concourse is having its premiere at Chicago’s world-class Steppenwolf Theatre. Full of both humor and heart, Heidi Schreck’s play, directed by ensemble member Yasen Peyankov, will strive to solve life’s essential questions. Tickets $20-$89, 1650 N. Halsted St., 312.335.1650

Getting Ready
Theaters are notoriously cold, so pop by the Vince boutique on Oak Street for a cozy cashmere cardigan to keep you company throughout the evening. $325, 106 E. Oak St., 312.280.6890

Pre-Theater Dinner
Balena offers a private prix-fixe dinner in its beautiful wine cellar. The rustic Italian restaurant features seasonal dishes from Chris Pandel and a Tuscany-inspired atmosphere. From $1,500, 1633 N. Halsted St., 312.867.3888

Post-Theater Drinks
This play is about redemption... but it’s a fairly rough road to get there. Best to cap the night off with a cocktail at Summer House—its laid-back California style will bring you back to the real world in a gentle way (and you might meet some cast members too). Cocktails from $12, 1954 N. Halsted St., 773.634.4100

A soup kitchen owner and a dropout meet. Find out what happens next at "Grand Concourse."

Lollapalooza Music Festival, July 31-Aug. 2

Nothing says summer in Chicago more than a festival. Lollapalooza invades Grant Park with Paul McCartney, Metallica and Florence + the Machine as headlining acts. Travel packages and platinum passes still available, from $1,735-$3,600, 337 E. Randolph St.

Getting Ready
What’s a festival without a braid or two? Get to primping with a braid bar for women, and haircuts and beard trimming for men, at Red 7 Salon’s VIP lounge in the Hard Rock Hotel Chicago. Trust us, you’re in good hands with this 11-time Lollapalooza haircare sponsor. 230 N. Michigan Ave., 312.345.1000

Your Hotel
Avoid the headache of finding a cab or parking spot in the city by booking your stay at The James, located just over a mile away from all the fun. The swanky River North hotel offers a three-night stay in a suite-style room with two platinum passes to Lollapalooza. $1,765-$9,039 for two individuals, 55 E. Ontario St., 312.337.1000

Your Chariot
Why walk when you can ride? The venue’s platinum pass provides a golf cart for each VIP group to cruise around the festival grounds at their leisure.

Ravinia Park Festival’s Tony Bennett and Lady Gaga, June 26-27
Ravinia’s annual summer series boasts an impressive contemporary lineup, including Tony Bennett and Lady Gaga, Santana and Rob Thomas. Sold-out shows are guaranteed, so we recommend that you purchase tickets as soon as possible. Tickets from $38, 200 Ravinia Park Road, 847.266.5000

Getting Ready
Summer heat is the kryptonite of good hair. Tonight, leave the styling to the pros with a long-lasting, red-carpetworthy blowout from DreamDry, the styling station co-founded by celebrity fashion expert Rachel Zoe. From $40, 904 W. Armitage Ave., 773.697.8172 

Your Chariot
Start the party early in a six-passenger stretch limo by Metropolitan Limousine. The bespoke private chauffeur service offers a special Ravinia package that allows passengers to completely customize their ride with drinks and mixers for the road. From $830, 1836 S. Wabash Ave., 312.808.8000

The Dinner

Skip the concessions and call ahead for the venue’s Lawncierge service. This outdoor VIP option serves groups of 50 to 200 with furnished lawn spaces, private wait staff and hosts, an open top-shelf bar and a custom dinner menu created by Levy Restaurants. Tickets $250, 200 Ravinia Park Road, 847.266.5087 

The Hypocrites’ All Our Tragic, June 20-Aug. 9
Progressive theater company The Hypocrites gives you your review of Western Civ all in one day, with a cash bar. The Chicago-based award-winning theater company reboots All Our Tragic, a 12-hour Greek theatrical event featuring the entire canon of Aeschylus, Sophocles and Euripides. Tickets $100-$125, 1329 N. Milwaukee Ave., 773.525.5991

Getting Ready
Start the marathon day off on the right foot—literally! Relieve sore muscles and revive skin with Mojo Spa’s signature Dr. Feel Good package, which includes a vitamin C mask, exfoliating scrub and mineral rich soak for hands and feet. $70, 1468 N. Milwaukee Ave., 773.235.6656 

Pre-Production Breakfast
Grab brunch at Mindy’s HotChocolate. The James Beard Foundation Award-winning chef Mindy Segal offers an ever-changing selection of sweet and savory treats like brioche French toast and duck-egg tartine. $9-$17, 1747 N. Damen Ave., 773.489.1747

Post-Production Cocktail
Keeping with the continental theme, hop over to Bangers & Lace. Rated one of America’s 100 best beer bars for the past four years by Draft magazine, this Wicker Park watering hole is the perfect way to end the night. 1670 W. Division St., 773.252.6499

Lookingglass Theatre’s Moby Dick, opens June 10
Call ahead for a buyout, grab some friends and set sail for a private performance of Moby Dick. This summer, Lookingglass Theatre will reimagine Herman Melville’s epic seafaring novel with acrobats and actors for its world premiere June 10. Buyout $7,300-$9,800, 821 N. Michigan Ave., 312.337.0665

The Dinner
Book The Whale Room at GT Fish & Oyster—a secret underground space that feels like the captain’s quarters. Have chef Giuseppe Tentori, a Charlie Trotter protégé, construct a custom menu (think sunfish ceviche, tuna poke and shrimp bruschetta) for you and your crew at the king’s table. From $1,500, 531 N. Wells St., 312.929.3501

The Drinks
Finish with a late-night snack at Nico Osteria’s Salone Nico. The Michelin-starred hot spot, located in the heart of Gold Coast, serves up tantalizing afterhours bites. And, so long as you’re there, call it a staycation. A short elevator ride away, the Thompson Hotel’s penthouse suite awaits with terrace views of the lake. From $1,500, 21 E. Bellevue Place, 312.266.2100

The Afterparty
Not ready to let the good times come to a close? See the show on a Saturday or Wednesday and finish the evening with a private boat tour, complete with fireworks. From $150 per hour, Chicago Electric Boat Company, 312.644.6411

Lyric Opera of Chicago’s Second Nature, Aug. 19-20
Lyric Opera of Chicago goes wild at Lincoln Park Zoo’s Cafe Brauer for the world premiere of Second Nature, composed by Matthew Aucion, who has been called the next Leonard Bernstein. Commissioned by Lyric Unlimited, the performance features all the quality of the world-class company, but not the stuffy atmosphere, so bring along your party animals (aka children). Free, 2021 N. Stockton Drive, 312.827.5600

Getting Ready
Remember, this isn’t your typical night at the zoo. Take a cue from Chicago-based designer Mikel Welch and pop by Suitsupply on Rush Street for a classic blazer, like the Havana Blue jacket made with Ferla linen—as fresh and lightweight as it gets. $499, 945 N. Rush St., 312.340.6909

Your Chariot
Hitch a ride in a horse-drawn carriage from Michigan Avenue or Old Town with Noble Horse Theatre. Or better yet, have Antique Coach & Carriage Co. pick you up from your humble abode and drop you right at the event. Private rentals from $100

Post-Opera Dinner

Afterward, head to Geja’s Cafe, a classic Chicago spot just down the street, for fondue—where you can dunk bread in cheese and talk it all over. Even closer is the legendary North Pond, a 2015 Michelin-star winner. 

The Museum of Contemporary Art’s The Freedom Principle: Experiments in Art and Music, 1965 to Now, July 11-Nov. 22
Get ready to groove with the Museum of Contemporary Art at an evening concert featuring avant-garde Chicago composer and artist Douglas R. Ewart (July 11, 7:30pm). This one-time-only affair at the MCA’s theater celebrates the unveiling of the museum’s summer exhibition, which explores African-American culture through the lens of jazz in Chicago. Tickets $30, 220 E. Chicago Ave., 312.397.4010

Getting Ready
Sexy and comfortable is a tall order when it comes to women’s shoes. Forgo an evening of pain with L.K.Bennett’s hair-calf pump. The brand’s popular style features a foam-padded sole and reinforced heel cap to keep you light on your feet. $425, 900 N. Michigan Ave., 312.374.0958

Pre-Gallery Dinner
Pelago Ristorante provides an elegant start to the evening. Chef Mauro Mafrici’s Italian cuisine features honest, genuine flavors used to create new sensations, forms and colors. That sensibility will get you in the proper mood for the concert. Raffaello Hotel, 201 E. Delaware Place, 312.280.0700

Post-Gallery Drinks
Afterward, how about a cocktail at the Signature Room on the 95th floor of the John Hancock Center? Try the Gin Rickey ($15) prepared with Koval Gin, fresh lime sour and club soda, while enjoying the glimmering views of the city. 875 N. Michigan Ave., 312.787.9596

DIFFA/Chicago Believe 2015 Imagine Ball, June 13
Join forces with business and industry leaders, as well as design enthusiasts from around the world, at the Design Industries Foundation Fighting AIDS annual Imagine Ball, one of the social calendar’s great dates. Tickets $500, Navy Pier Grand Ballroom, 600 E. Grand Ave., 312.644.6412

Getting Ready
Your go-to dinner jacket or LBD might not suffice for such a spectacular evening. For men, reserve a formal gala-appropriate tuxedo with Formally Modern Tuxedo, which features the city’s best selection of traditional and trending dinner jackets from makers like Perry Ellis and Ike Behar. Ladies can look to Rent the Runway for something extra-special, like a full-length gown from Bibhu Mohapatra. Tuxedos $169-$189, Formally Modern Tuxedo, gowns $80-$750, Rent the Runway, 710 N. Wabash Ave. 312.288.7570 

Your Chariot
Call ahead to Chicago Exotic & Luxury Car Rentals and secure a Rolls-Royce Phantom from its fleet to arrive in impeccable style. $450 per hour, 10 S. Riverside Plaza, 312.204.7227

Afterparty Celebration
The gala ends at midnight, but that doesn’t mean you have to go home. Retire to Sable Kitchen & Bar at Hotel Palomar when the night officially winds down and wind it all back up again with a more intimate celebration. 505 N. State St., 312.755.9704