Chicago Vacations

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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.

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.

Chicago Vacation Packages

Free Cancellation
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20 E. Delaware Map
4.6 / 5 1444 reviews
  • Last Minute Deal!
  • Last Minute Deal!
Hotel only
$135

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, with cosy, open-fire warmth in the lobby and 1920s... More

Hotel only
$135
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127 W Huron Map
4.4 / 5 160 reviews
Hotel only
$115

The Godfrey Hotel in Chicago is a modern luxury boutique hotel in the heart of a bustling neighborhood. Its spacious rooms, stunning city views and abundant amenities make it a great choice for both business and leisure travelers. Business travelers will appreciate the... More

Hotel only
$115
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166 East Superior Street Map
4.3 / 5 464 reviews
  • Save 15% on your stay
  • Save 15% on your stay
Hotel only
$100

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 are best spent enjoying appetizers and sipping cocktails at the 52Eighty rooftop... More

Hotel only
$100
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701 North Michigan Avenue Map
4.0 / 5 609 reviews
Hotel only
$89

An original tower block dating back to the Jazz-Age in Chicago, the Warwick Allerton Hotel Chicago has a well-preserved Renaissance-style facade, with lingering touches of Art Deco streamlining in its rooms and lounges within. As a part of Warwick International Hotels,... More

Hotel only
$89
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800 S Michigan Avenue Map
3.7 / 5 275 reviews
  • Save 15% on your stay
  • Save 15% on your stay
Hotel only
$66

Chicago's Essex Inn in Chicago blends in perfectly in the heart of the Windy City. For guests who want to relax and retreat, the free rooftop pool and state-of-the-art fitness facilities make it easy to do so. The pool is enclosed with glass and is all-season, allowing... More

Hotel only
$66
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455 North Park Drive Map
4.5 / 5 18 reviews
  • Grand Opening Special - Save 30% on your stay
  • Grand Opening Special - Save 30% on your stay
Hotel only
$107

Booking a room at the Loews Hotel in Downtown Chicago and you ll stay at one of the most modern hotels in the area. Loews opened in March of 2015 and hosts 400 guest rooms as well as 25 suites. No matter which type of room you book, you ll be able to choose from a view of... More

Hotel only
$107
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660 N State St Map
4.2 / 5 237 reviews
Hotel only
$125

Located a few miles inland of Lake Michigan and within walking distance of Chicago's famed Magnificent Mile is the luxurious Dana Hotel & Spa. This boutique-style hotel and spa evokes pleasure and relaxation with modern, artistic decor throughout the property. The... More

Hotel only
$125
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151 East Wacker Dr Map
4.1 / 5 745 reviews
  • Includes Free Valet Parking
  • Includes Free Valet Parking
Hotel only
$114

Experience the mid-city excitement of Chicago with a stay at the Hyatt Regency Chicago, one of the glorious pillars of The Windy City s urban landscape, which delivers everything on a large scale. Expansive open-plan areas are flanked by sloping staircases and sprawling... More

Hotel only
$114
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111 W Huron Map
4.0 / 5 146 reviews
  • Save 15% on your stay
  • Save 15% on your stay
Hotel only
$112

As you enter the lobby of the Hotel Felix in Chicago, you'll be greeted by a pond surrounded by wooden logs and colorful orbs, highlighting the environmentally friendly motif of the hotel, which boasts Silver LEED certification from the U.S. Green Building Council.... More

Hotel only
$112
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111 West Adams Street Map
4.0 / 5 300 reviews
  • Save 10% On Your Stay
  • Save 10% On Your Stay
Hotel only
$79

Located in the heart of The Loop in Chicago, the Central Loop Hotel that provides its guests with four different room types to choose from as well as two studio apartments if you re going to have an extended stay. Each room comes with complimentary high-speed wireless... More

Hotel only
$79

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.

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  • Promo Code Terms and Conditions

    50VACA
    Book a qualifying 4-night flight + hotel vacation package between January 1, 2014 12:00AM CT and March 31, 2016 11:59PM CT, for $1000 or more for travel between January 1, 2014 and June 30, 2016, via Orbitz and instantly receive $50 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.