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.

  • 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.

  • 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

Hotel only $162

1 The Talbott Hotel

4 stars
4.6 / 5 1326 reviews

20 E. Delaware Map

Last Minute Deal!

The Talbott Hotel is a European-style resort, which is reflected by the Italian Frette linen you'll find in each of its guest rooms. This AAA Four Diamond Hotel is a member of the Historic Hotels of America, as well as being one of the first Green Seal-certified hotels in... More

Hotel only $115

2 Warwick Allerton Hotel Chicago

4 stars
4.0 / 5 587 reviews

701 North Michigan Avenue Map

The hotel's arguably best views are usually found at the corner suites on the upper floors. Don't forget to end the day with a classic deep-dish Chicago 'pizza pie' at Gino's East. GeneralWarwick Allerton Hotel Chicago, Magnificent Mile, Chicago LocationAn original... More

Hotel only $126

3 The Godfrey Hotel Chicago

4 stars
4.4 / 5 144 reviews

127 W Huron Map

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

Hotel only $91

4 Inn of Chicago, an Ascend Collection hotel

3 stars
3.5 / 5 258 reviews

162 East Ohio Street Map

In the Roaring '20s, this boutique Streeterville hotel hosted celebrities and showgirls. While those times have faded, the air of glamour remains at the Inn of Chicago, an Ascend Collection hotel. For proof, just stroll the lobby, where zebra ottomans, fresh-cut orchids... More

Hotel only $126

5 Hotel Felix

4 stars
3.9 / 5 133 reviews

111 W Huron Map

Save 15% on your stay

A hotel that offers luxury yet cares for the environment? That's Hotel Felix. Located downtown, the Hotel Felix Chicago offers guests a variety of excellently priced rooms and amenities with an eco-friendly approach. Hotel Felix greets guests with a surprisingly modern... More

Hotel only $115

6 Chicago's Essex Inn

3 stars
3.7 / 5 257 reviews

800 S Michigan Avenue Map

Save 15% on your stay

Chicago'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 attractions, including Millennium Park and the Art Institute. Sleek... More

Hotel only $127

7 Raffaello Hotel

4 stars
4.0 / 5 290 reviews

201 E. Delaware Place Map

Stay 3, Save 15%

Check out Pelago Ristorante at least once during your stay, since it's helmed by Michelin star-rated chef Mauro Mafrici. GeneralRaffaello Hotel, Chicago, Illinois LocationMenin Hospitality operates several luxury boutique hotels in Miami and a single hotel in Chicago,... More

Hotel only $223

8 Chicago Suites

4 stars
Not yet reviewed

875 North Dearborn Street Map

Located in Gold Coast, this building is within a 5-minute walk from Newberry Library and Hancock Tower. Chicago Water Tower and Tribune Tower are 15 minutes away. A business center, a convenience store, and barbecue grills are available at this building. WiFi in public... More

Hotel only $120

9 Club Quarters, Central Loop

3 stars
4.1 / 5 542 reviews

111 West Adams Street Map

Save 15% On Your Stay

The Club Quarters Central Loop hotel might be mistaken for an office building with its subdued presence. A black awning marks this discrete spot and lends a sense of privacy. The hotel targets business travelers whose work brings them to the financial district and... More

Hotel only $208

10 The Drake Hotel

4 stars
4.3 / 5 192 reviews

140 East Walton Place Map

Rate includes Breakfast

Search ResultHistoric hotel with afternoon tea near shopping More

  • Promo Code Terms and Conditions

    100TRIP
    Book a qualifying 4-night flight + hotel vacation package between August 13, 2015 12:00AM CT and September 30, 2015 11:59PM CT, for $1000 or more for travel between August 13, 2015 and December 31, 2015 via Orbitz and instantly receive $100 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
  • 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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