For High Rollers
The 67-story Park Hyatt Chicago is a flagship for the brand. Centrally located in the Loop on Michigan Avenue, the hotel offers rooms fitted with mid-century-modern seating, glass and chrome details, and killer views. Nomi Restaurant remains a standout dining destination for locally grown, seasonally inspired cuisine.
800 North Michigan Avenue
From $360 per night
(Courtesy: Longman and Eagle)
Where the Cool Kids Are
Longman and Eagle caters to a select few simply by dint of the lack of rooms—there are only six at the hotel, which is above the restaurant of the same name. The look of each room is unique, with custom artwork on display on a rotating basis, Apple TV, and, occasionally, items like old Fisher-Price cassette players. The rooms are not gigantic, but they are ideal for stumbling home after an inventive nose-to-tail meal downstairs.
2657 North Kedzie Avenue
From $85 per night
(Courtesy: Primehouse at The James)
Still vibrant after nearly a decade, The James is the blueprint for many of Chicago’s chic hotels. Offering nearly 300 rooms, it’s generally bustling, especially at David Burke’s Primehouse restaurant, which slings his whimsical, crowd-pleasing spins on comfort food (donuts! bacon on everything!). Many rooms have separate sitting areas, and all have separate dining areas, giving guests some breathing room in the clean, modern space with blonde wood and blocky furnishings.
55 East Ontario Street, Chicago
From $269 per night
(Courtesy: The Godfrey)
Debuting in February 2014, The Godfrey in River North comes with impressive credentials. The abstract Cubist exterior (created by Chicago-based architecture firm Valerio Dewalt Train), dubbed “Jenga chic,” hides a more comfortable interior (though the swoopy flourishes in the lobby are a whimsical touch). Rooms have large flatscreens, and many manage to cram in sitting rooms separate from the sleeping area. The rooftop space, called I/O, has retractable glass walls in order to handle Chicago’s climate.
127 West Huron, Chicago
From $129 per night
Take a short taxi ride north on Michigan Avenue to the clubby confines of RL restaurant, which is attached to the Ralph Lauren flagship store and is the city’s reigning power-lunch spot. Look for current and former mayors, financial heavy hitters, and socialites splurging on the decadent lobster club. Reservations are recommended at peak times; ask for Oprah’s booth or a banquette table near the host stand.
115 East Chicago Avenue
(Photo: Tim Welbourn/Flickr)
A modern Jewish deli, Eleven City Diner in the South Loop has great sandwiches and soups, classic malts, and thick shakes, as well as full dinners. Best of all? It also has “adult beverages” to help you relax after the long day.
1112 South Wabash Avenue
Meat and Greet
No bachelor party weekend is complete without a big steak dinner, and Chicago Cut, overlooking the Chicago River, is one of the best in the city. With dry-aged prime steaks, big-ass bottles of red (viewable via iPad list), and killer views, this is the joint. In warm months, reserve a table on the patio on the river.
300 North LaSalle
Famed chef Jean-Georges Vongerichten crafted this menu at the Pump Room, reincarnated from a storied classic Chicago restaurant. Get house-made doughnuts, challah French toast, “sunny-side-up” frittata, and more. The Bloody Marys and mimosas kick off the day right, or opt for something else from the full bar.
1301 North State Parkway
She dresses Michelle Obama and is the city’s famous—and sometimes fearsome—queen of fashion. Walk a few blocks southwest to the red-lacquer box that is the fabulous new location of Ikram, the clothing store (there’s also an art gallery and a café for the ladies who lunch), where taking in the cutting-edge styles by a host of international designers is equally fun whether you’re buying or not.
15 East Huron Street
Up the River
Keep the day going with an architectural tour on the Chicago River. The three-hour tour, at $65 a head, paddles you into the Loop while getting an up-close history of the city and the buildings that line the river’s banks.
1501 North Magnolia Avenue
(Courtesy: Frank Lloyd Right Trust)
The enclave of Frank Lloyd Wright homes in the nearby suburb of Oak Park is always a draw for architecture lovers, but his Robie House in the leafy South Side neighborhood of Hyde Park—also home to the University of Chicago and one Barack Obama—is more convenient. It is a beautiful, important example of Wright’s Prairie style. (On the way there, cruise past the corner of Greenwood Avenue and Hyde Park Boulevard to catch a glimpse of POTUS’s red-brick manse.)
5757 South Woodlawn Avenue
It’s a Zoo
The Peggy Notebaert Nature Museum is a quick walk through Lincoln Park, by the zoo, and past the Conservatory. Once inside, it’s a marvel for all ages. Don’t miss the Butterfly Haven. With more than 75 species freely flying around, they’re bound to land on the kids.
2430 North Cannon Drive
5 Things to Know
1. Must-try Chicago culinary items: Garrett popcorn, Chicago-style hotdogs, and deep-dish pizza (for the latter, best make it Lou Malnati’s).
2. Chicagoans take their beer seriously and have the beer-centric bars to prove it. On our list of faves are the Local Option, Map Room, and Hop Leaf.
3. Swing by Chicago’s top three towers for insane views: Willis Tower (formerly Sears), Trump Tower, and the John Hancock Center.
4. Just a quick walk north, those who crave comedy will find their fix at Second City. Located in the Old Town neighborhood, the bars along Wells Street will provide the perfect post-show refreshment.
5. Culture and art seekers will love the Hispanic Pilsen neighborhood, known for street art, independent galleries, and its signature “Art Walk.”