/
Close
Newsletters  | Mobile
  • Print
  • Share
  • Map

The Latest Chicago Itinerary

Today, Chicago mixes innovative architecture with green spaces, cutting-edge cuisine with hot dogs and pizza, and world-class shopping with independent boutiques. Its cultural scene boasts great museums, celebrated blues joints, and a superb theater scene that includes Steppenwolf, Second City, and the Goodman—all of this in a prime location on the shores of shimmering (and often windy) Lake Michigan.

Hotels (8)

Open / Close
  • No_image

    Hotel Blake

    Fusing boutique-hotel modern with the historic architecture of the Printers Row neighborhood, the Blake’s 19th-century Morton Salt building façade

    ... More
  • No_image

    Hotel Indigo, Chicago

    Finding what looks like the interior of a seaside resort in the middle of this swanky Gold Coast neighborhood can be a little disorienting, but as

    ... More
  • No_image

    The Beldon-Stratford Hotel

    Built in 1923 and featuring a grand, hushed lobby topped with a ceiling mural of clouds in the sky, the Belden-Stratford offers the “Eloise at the

    ... More
  • 2011-v-james_standard_thumb

    The James, Chicago

    Opened in April 2006, The James marries a residential vibe to a hotel setting. To evoke an apartment style, all of the 297 contemporary rooms have

    ... More
  • 2011-tl500-drakechicago_standard_thumb

    The Drake

    As the preferred stop for visiting heads of state, the Drake is the grande dame of Chicago hotels, with a prime location, storied history, white-gl

    ... More
  • No_image

    Hotel Burnham

     

    Perhaps no other hotel showcases Chicago’s impressive architectural history like the Burnham. The historic 1894 Reliance Building was lavishly r

    ... More
  • 201101-a-hotel-peninsula-chicago_standard_thumb

    The Peninsula Chicago

    As you walk into the Peninsula, the concierge and receptionist greet you by name; classical music plays when you enter one of the 339 rooms; and yo

    ... More
  • Tl500-a-usa-sofitel-chicago-tower_standard_thumb

    Sofitel Chicago Water Tower

    Paris flirts with the Midwest at Sofitel’s North American flagship property. The 32-floor glass prism, Parisian-inspired restaurant (Café des Archi

    ... More

Restaurants (9)

Open / Close
  • No_image

    Billy Goat Tavern

    Immortalized by the 1970’s Saturday Night Live skit in which a short-order cook (John Belushi) screamed “Cheezborger! Cheezborger! No fries, cheeps

    ... More
  • No_image

    Wishbone

    Just steps away from Oprah’s Harpo Studios, the unfussy Wishbone is a favorite among staffers for southern-inspired fare that tends toward the ligh

    ... More
  • No_image

    Podhalanka Polksa Restauracja

    Unless you knew to look for it, you’d probably never notice the dingy storefront of this local secret—and that would be a shame. The interior, remi

    ... More
  • No_image

    Gene & Georgetti

    Aside from the absence of cigarette smoke, it’s hard to imagine that this classic steak-and-seafood place has changed much since it first opened in

    ... More
  • No_image

    Spacca Napoli

    Inspired by the traditional pizzerias in Naples, this Ravenswood eatery is known for its authentic, fresh ingredients. True to tradition, Spacca Na

    ... More
  • No_image

    Lula Cafe

    This hip Windy City café is another big supporter of fresh ingredients from regional markets and farmers. There's always a "griddle cake" on the me

    ... More
  • No_image

    Avec

    Inspired by the wine-making regions of Europe, this West Loop wine bar is the sister restaurant to neighboring Blackbird. The main attraction here

    ... More
  • No_image

    Alinea

    At the forefront of the groundbreaking molecular gastronomy movement, Alinea offers meals that are quite simply unlike any others. Dedicated follow

    ... More
  • No_image

    Irazu

    On a wood plank sign, colorful markers advertising authentic Costa Rican dishes welcome visitors to this family-owned café in Bucktown. In addition

    ... More

Activities (26)

Open / Close
  • No_image

    The Green Mill

    Said to be the country’s oldest jazz club, The Green Mill has been a Chicago landmark for more than a century. Beneath its sparkling green neon sig

    ... More
  • No_image

    Le Bar at The Sofitel

    With overstuffed royal-purple chairs, a French oil painting, and architectural books scattered throughout, Sofitel’s Le Bar feels like a nobleman’s

    ... More
  • No_image

    The Bar at The Peninsula

    This elegant cocktail lounge, located on the ground floor of Chicago's Peninsula hotel, is a popular after-work hangout for locals and travelers in

    ... More
  • No_image

    The Signature Lounge

    Instead of visiting the John Hancock Center’s zenith during daylight hours, opt for an evening cocktail in the building’s high-flying lounge. Locat

    ... More
  • No_image

    Garrett Popcorn

    Stroll down the Magnificent Mile and stop at Garrett Popcorn. Although the company now has stores throughout Chicago and New York City, the first o

    ... More
  • No_image

    Gem

    From a wood and amethyst ring to white gold and blue topaz earrings, Gem showcases one-of-a-kind handmade accessories. In 2004, Laura Kitsos opened

    ... More
  • No_image

    Alternatives Shoes

    Located in a very popular shopping area along North Michigan Avenue, Alternatives not only stays ahead of current trends, but has been know to insp

    ... More
  • No_image

    Guise | Chic

    Get a haircut, shop for new outfits, and watch TV—all at the recently opened Guise|Chic. Owners Brad Habansky, Heidi Taylor, and Jodi Immel transfo

    ... More
  • No_image

    Veruca Salt Fun

    Whether you want a pair of skinny jeans or a black cocktail dress, visit sister stores Veruca Salt Fun and Veruca Salt Fancy. For basics like Grass

    ... More
  • No_image

    Veruca Salt Fancy

    Whether you want a pair of skinny jeans or a black cocktail dress, visit sister stores Veruca Salt Fun and Veruca Salt Fancy. For basics like Grass

    ... More
  • No_image

    Robin Richman

    From her own clothing line to the commissioned skirt-form sculpture hanging from the ceiling, owner Robin Richman displays her touch everywhere in

    ... More
  • No_image

    Sugar Magnolia

    Named for the famous Grateful Dead tune, this Oak Street boutique has been a Chicago standby since it opened in 1972. Chic yet comfortable separate

    ... More
  • No_image

    The Magnificent Mile

    Chicago’s answer to New York’s Fifth Avenue and Beverly Hills’s Rodeo Drive, the Magnificent Mile is the city’s shopping and dining mecca. The resu

    ... More
  • No_image

    The Second City

    Founded in 1959 by Alan Arkin and several cohorts, this comedic theater company has been the training ground for the likes of John Belushi, Mike My

    ... More
  • No_image

    House of Blues

    Once a historic movie theater, the two-story venue transformed itself in 1996 as an outlet for up-and-coming jazz, R&B, funk, and hip-hop musicians

    ... More

Similar Trips (7)

Open / Close
  • Green Travel in Chicago

    Chicago, The Loop, Near North

    Blessed with a crop of sustainably-minded restaurants, energy-efficient public transportation, and the wide green oasis of Milennium Park, Chi-Town is a green traveler's haven.

  • Mini Trip: Performing Arts in Washington, D.C.

    Penn Quarter, Dupont Circle, Gold Coast, Chinatown/Convention Center, Foggy Bottom

    Catch a performance at the Kennedy Center's free Open House Arts Festival, wine and dine, and go undercover at the International Spy Museum.

  • Driving Trip: Chicago to Harbor Country

    Chicago, Union Pier, Sawyer, Lakeside, Indiana

    Harbor Country, Michigan, a cluster of eight lakefront communities connected by windy, tree-lined back roads, is the weekend getaway of choice for Windy City residents (including Oprah!).

  • Mini Trip: Chicago's North Avenue Beach

    Chicago, Lincoln Park, River North

    A short drive from downtown, you'll see everyone from lobster-red Ditka fans to bronzed, buff young professionals swimming, sunning, and spiking volleyballs.

  • Chicago Hot Dog Crawl

    Chicago, Lincoln Park, River North, Lakeview, Avondale

    Ever since Austro-Hungarian immigrants Emil Reichel and Sam Ladany introduced Vienna-style sausages at Chicago’s 1893 World’s Fair, “wieners,” also known as red hots, have been the city’s essential...

  • The Midwest: An Architecture Buff's Tour

    Milwaukee + Lake Michigan Area, Minneapolis/St. Paul, Spring Green, Toledo, Downtown Minneapolis

    It's no secret anymore: The Midwest is home to some of the most innovative contemporary architecture in America. Our five day self-guided tour includes stops in Toledo, Milwaukee, Minneapolis, and

    ...

  • Touring Chicago's Hottest Tables

    Western Springs, Lincoln Park, River North, South Loop, Wicker Park/Bucktown

    Though chefs like Charlie Trotter and Rick Bayless long ago helped Chicago shed its "Hog Butcher for the World" image, the city hasn't quite been able to edge past the dining capitals on the coasts...

Advertisement

Sign Up


Connect With Travel + Leisure
  • Travel+Leisure
  • Tablet
  • Available devices

Already a subscriber?
Get FREE ACCESS to the digital edition


Advertisement


Advertisement

Advertisement

Marketplace