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Experience the best of Chicago
With a global smorgasbord of restaurants, bars, music venues and architectural landmarks, Chicago is by no means a Second City. A Chicago vacation brings year-round thrills, whether you're catching the opening pitch at Wrigley Field or riding the famous El.
Before you admire your reflection in Cloud Gate (aka "The Bean") or hit a skyline cruise on Lake Michigan, allow Orbitz to help you with the planning. Enjoy the intel from our insider guide, from the top 10 attractions to tips from local experts.
Tourists flock to Chicago during spring and summer, when Chicagoans emerge from hibernation into outdoor cafes, legendary sports stadiums and the city's gorgeous parks for music, food and cultural festivals including the Taste of Chicago and Lollapalooza.
If a Chicago vacation happens during the winter, pack a down coat and take advantage of off-peak rates at downtown Chicago hotels. The city's public transportation is among the best in the nation, making it easy to travel to museums, bars, restaurants, landmarks and even far-flung locations in the suburbs.
For great people watching and impressive skyline views, hit Oak Street Beach, where singles flock to play volleyball and sunbathe. Families stick to Montrose and Loyola beaches a little further north, which are a lot less crowded and pose better chances for finding a parking spot.
Kit Kat Lounge
Shake up your Sunday brunch with the bottomless mimosas and drag shows at Kit Kat Lounge, Boys Town's favorite martini bar and lounge.
Looking for an offbeat place for cocktails in one of Chicago's hippest neighborhoods? Consider the Bedford in Wicker Park, located in a former bank building. Imbibe old-school cocktails in the actual vault, which is dotted by safe deposit boxes.
For a leisurely lesson on Chicago's architecture, catch a boat cruise from Navy Pier or at the bottom of the Wrigley Building.
If you're planning to visit this famous restaurant, book your reservation at least two months in advance. If you do score a table, don't be discouraged if you can't spot the restaurant immediately. It's in a grey brick storefront with no sign.
Chicago Vacation Packages
This boutique property offers a residential-style retreat that soars above Chicago's Magnificent Mile. Each floor is home to no more than 11 spacious guest rooms and suites, and your evenings would be well spent enjoying appetizers and sipping cocktails at the 52EIGHTY... More
As one of the first high-rises to grace Chicago's fashionable Michigan Avenue, the Warwick Allerton Hotel Chicago became synonymous with high style, luxurious hotel accommodations and impeccable service. Today, the hotel has kept the commitment to treat every guest like... More
Step into the lobby of Palmer House® A Hilton hotel and gaze at the famous frescoed ceiling of this landmark Chicago, Illinois hotel. This AAA four-diamond rated hotel has been hosting visitors to the Chicago Loop for over 140 years. Today, the Palmer House Hilton... More
Godfrey means peace and welcome; welcome to The Godfrey Hotel Chicago. The Godfrey Hotel Chicago offers unforgettable style from the Cubist-influenced facade to the chic accommodations, each detail of this striking new hotel has been designed with the guest's experience... More
Affordable hotel south of Chicago's bustling downtown areaChicago's Essex Inn has an ideal location ideal on Michigan Avenue, just a few blocks south of the more congested areas of downtown Chicago. Grant Park is across the street, along with many famous Chicago... More
22 W. Monroe Map
Free On The House hot breakfast, Wi-Fi
Comfort and sophistication in a cultural settingThe Hampton Inn Majestic Chicago Theater District is situated above the Bank of America Theater, which has hosted productions by a number of celebrities, including Billy Joel. The convenient location in the heart of the... More
Independently-owned and with a dedication to green practices, The Talbott Hotel has been a fixture in Chicago's Gold Coast neighborhood since 1927. The hotel mingles old-world sophistication with modern conveniences - the lobby has a cozy, open-fire warmth and the... More
Access to attractions, plus free Wi-Fi and indoor poolGuests at the Hotel Rush enjoy a plum location just off the Magnificent Mile. Whether the agenda is hitting downtown shops, restaurants, bars or landmarks, leisure travelers will find no shortage of... More
Menin Hospitality operates several luxury boutique hotels in Miami and a single hotel in Chicago, the Raffaello Hotel. This cozy boutique hotel is situated right on Michigan Avenue, very close to some of the most celebrated attractions and amenities on the Gold Coast and... More
Original boutique hotel in the heart of the Gold CoastThe Thompson Chicago offers top tier facilities with understated elegance to leisure and business travelers alike. This four diamond property originally opened in 1988 as Hotel 21 East, and was re-launched as Sutton... More
Promo Code Terms and Conditions
Book a qualifying 4-night flight + hotel vacation package between January 1, 2014 12:00AM CST and June 30, 2015 11:59PM CST, for $1000 or more for travel between January 1, 2014 and September 30, 2015 via Orbitz and instantly receive $150 off the hotel portion of your booking through the use of the promotion code. Limit one discount per hotel room and one promotion code per booking. Discounts are not redeemable for cash for any reason. Promotion codes cannot be resold. Any attempt at fraud will be prosecuted to the fullest extent of the law. Void where prohibited, taxed or restricted. Orbitz reserves the right to change or limit the promotion in its sole discretion. Promo code not valid for Las Vegas, NV bookings.
Chicago's most fashionable boulevard is at the center of the downtown action. Lined by colorful tulips in the springtime and white lights during the holidays, the Mag Mile is as flashy as its posh department stores and notable landmarks, from the Wrigley Building to the historic Drake Hotel.
Capture your postcard moments along the way, starting with a snapshot of the stone fragments from landmarks around the world affixed to the Tribune Tower.
Art Institute of Chicago
Housing more than 300,000 works of art, this Michigan Avenue gem spans centuries' worth of masterpieces, from the "A Sunday on La Grande Jatte" by Seurat and "American Gothic" by Grant Wood. A 2009 expansion enhanced the appeal thanks to the super sleek Modern Wing designed by Pritzker Prize–winning architect Renzo Piano.
The Ryan's Education Center invites the tykes to engage in their environment with interactive exhibits. Organic restaurant Terzo Plano fuels the romance with glorious views of the Pritzker Pavilion.
Home to Cloud Gate, Crown Fountain, the Jay Pritzker Pavilion and more attractions, the park leaves visitors impressed by striking landmarks, lake access and buzz from the neighboring Magnificent Mile.
The best part: Many summer activities are free, including outdoor yoga and Pilates, Chicago SummerDance, and the Family Fun Festival at Chase Promenade North.
Its name may have changed, but in the hearts of Chicagoans, Willis Tower will always be Sears Tower. The building soars 110 stories above the Windy City, and is home to the world's tallest green roof on the 90th floor. The Skydeck invites visitors to look down at the metropolis via clear ledges, but only if you dare.
No curse can deny Chicago's unwavering love for the Cubs -- and it's as much about the scene as it is about the fantasy of winning a World Series. And it doesn't get any more Chicagoan than seeing fans swig beers during a rowsing rendition of "Take Me Out to the Ball Game," or cheering from the rooftop decks in Wrigleyville. Expect as much flavor surrounding the stadium, as diehards continue the party along Clark, Addison and Waveland.
The Signature Lounge at the John Hancock
Take the elevator up 96 flights to soak in the views from the Signature Lounge, the best seat in Chicago. While there is no admission fee, expect pricy cocktails -- but paired with floor-to-ceiling panoramas of the Windy City, they're worth it.
If time permits, opt for the Sunday brunch or a special occasion dinner at the Signature Room, equally dazzling with oversized windows and an impressive wine list.
If the careers of John Belushi, Gilda Radner, Tina Fey, Mike Meyers and Steve Carrell have proven anything, it's that a stop at Second City could help rocket a career. The talent incubator in the heart of Old Town hosts both sketch-based and improv performances in an intimate setting.
Expect to feel like a kid again throughout the lakeside treat, which boasts a Ferris wheel, the Chicago Children's Museum, Chicago Shakespeare Theater, bikes for rent, boat rides, miniature golf and headlining acts such as Cirque Shanghai Extreme.
Come summertime, pull up a chair at an al fresco restaurant -- Harry Caray's is a favorite -- to watch the twice-weekly fireworks.
Chicago is blessed with an 18.5-mile path along the shores of Lake Michigan, a stretch bustling with bikers, runners, soccer fields, beaches and parks. Connecting neighborhoods as far south as the South Shore to as far north as Edgewater, the path is an easy way to combine sightseeing with recreation.
Buddy Guy's Legends
Chicago never sounded so sweet than at this iconic blues den in the South Loop. The stage jams seven nights a week – with heavy hitters such as Eric Clapton and John Mayer among the past featured acts.
For a side of Cajun spice to go with your blues, order from a menu of Southern classics, including okra, gumbo and jambalaya.
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