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Chicago Vacations

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Chicago vacations

Your Chicago vacation guide

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.

Best time to take a vacation to Chicago

  • 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.

Insider tips for Chicago travel

  • Beaches

    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.

  • Cocktails

    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.

  • Boat tours

    For a leisurely lesson on Chicago's architecture, catch a boat cruise from Navy Pier or at the bottom of the Wrigley Building.

  • Alinea

    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.

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Chicago Vacation Packages

Hotel only $79

1 Congress Plaza Hotel at Grant Park

520 South Michigan Ave Map

Save 10% on your stay

Historic hotel on Michigan Avenue by Grant ParkGuests at the Congress Plaza Hotel at Grant Park hotel enjoy value prices and a convenient location across from Grant Park, Buckingham Fountain, Millennium Park, the Art Institute and Lake Michigan. Designed to accommodate... More

Hotel only $145

2 The Talbott Hotel

20 E. Delaware Map

Save 20% on your stay

This Property is 100% Non-Smoking. The Talbott Hotel in the heart of the Gold Coast offers spacious rooms with complimentary amenities including wireless internet and access to Equinox Fitness. Located steps from Chicago's Magnificent Mile and Rush Street, the heart of... More

Hotel only $112

3 The Whitehall Hotel

105 E. Delaware Place Map

Save 20% on non-refundable with advance purchase

Gold Coast boutique meets 1920s charm The Whitehall Hotel manages that rare combination of location and ambiance. The hotel is situated one block from the Magnificent Mile and Rush Street nightlife district, but tucked away from the tourist fray on a residential street.... More

Hotel only $99

4 Raffaello Hotel

201 E. Delaware Place Map

Stay 3 nights, Save 35%

Boutique luxury in the heart of the Gold Coast In Chicago, the rule for downtown real estate is the closer to Lake Michigan, the more posh the address. Enter the Raffaello Hotel, a four-star hotel just steps from the lake and Magnificent Mile with a Michelin-rated chef... More

Hotel only $158

5 Kinzie Hotel (formerly the Amalfi Hotel)

20 West Kinzie Street Map

Grand Opening Special - Save 25% on your stay

Boutique chic at convenient Chicago hotelThis River North hotel defines the term boutique chic with its intimate, yet contemporary style. The space creates a relaxing experience for business and leisure travelers. Kinzie Hotel features well-appointed units and places... More

Hotel only $79

6 Chicago's Essex Inn

800 S Michigan Avenue Map

Save 15% on your stay

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

Hotel only $89

7 Best Western Grant Park

1100 S Michigan Avenue Map

Catch a ball game, visit major museums, relax on a budgetThe Best Western Grant Park Hotel offers visitors a great downtown location to take in all of Chicago's main attractions. Chicago's hustling and bustling Loop district, Millennium Park, Soldier Field (home of the... More

Hotel only $109

8 MileNorth, A Chicago Hotel

166 E Superior Street Map

Advance Purchase Savings - Save 10%

Magnificent Boutique Hotel in Downtown Chicago Steps from the Magnificent Mile, the MileNorth Chicago features a prime location at the Windy City's epicenter of shopping, entertainment, culture and business. Known for its fast pace, famous museums, amazing architecture,... More

Hotel only $139

9 The Silversmith Hotel Chicago

10 South Wabash Avenue, Map

Save 15% with advance purchase

Landmark in the Loop near attractions and shoppingIt's only fitting that this historic hotel is just a few blocks from Jewelers Row given its name and former purpose. In the 1890s, its tenants worked in the jewelry and silver trade. Today, landmark elements -- a cast iron... More

Hotel only $89

10 Millennium Knickerbocker Hotel

163 Walton Place Map

Save 15% on your stay

Chicago hotel on Magnificent Mile with hip martini bar and restaurantIn 1927, notable architects Rissman & Hirschfield, responsible for many highlights on the Chicago skyline, finished a 14-story, gothic-inspired hotel that is now known as the Millennium Knickerbocker... More

Chicago highlights

  • Chicago
  • Magnificent Mile

    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.

  • Millennium Park

    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.

  • Willis Tower

    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.

  • Wrigley Field

    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.

  • Second City

    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.

  • Navy Pier

    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.

  • Lakefront Trail

    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.