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
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.
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.
For a leisurely lesson on Chicago's architecture, catch a boat cruise from Navy Pier or at the bottom of the Wrigley Building.
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.
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.
More on Chicago from the Orbitz Blog
Chicago Vacation Packages
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 Chicago's night life. Voted as an... More
520 South Michigan Ave Map
Save 20% 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
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
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
701 North Michigan Avenue Map
Save 15% on your stay
As one of the first high-rises to grace Chicago's fashionable Michigan Avenue, The 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 a... More
You enter the SAX Hotel experience through a lobby that has Attitude with a capital A. White marble floors, ruby leather wing-backed chairs and the sparkle of crystal chandeliers are all part of its Bohemian charm. Call it stylish. Call it contemporary. The thing is,... More
151 East Wacker Dr Map
Welcome Pack with $100 USD Macys Gift card & cpns
Convenient convention hotel in ChicagoWhen the lights go down in the Windy City, there is no better location to soak in the view than at the Hyatt Regency Chicago. To the north of this downtown hotel lies the Chicago River and to the east sits the unmistakable Navy Pier... More
Modern retreat for healthy living in downtown ChicagoThe dana hotel and spa in Chicago's River North neighborhood balances the beauty of natural elements with the latest technology to create a modern retreat for healthy living. From the progressive health center to the... More
66 West Illinois Street Map
Save 25% on your stay
Hyatt Place Chicago River North with 212 contemporary suites is located just north of the Loop in the citys most spectacular neighborhood to shop, dine, play and stay. In terms of Chicago River North hotels, our location couldn't be more convenient. Vacationers will find... More
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
Flights to Chicago
|New York||Chicago||Wed, Jan 8 - Wed, Jan 22||$148|
|Los Angeles||Chicago||Wed, Jan 29 - Wed, Feb 5||$188|
|Washington DC||Chicago||Thu, Jan 23 - Fri, Jan 24||$210|
|Denver||Chicago||Fri, Jan 31 - Tue, Feb 4||$138|
|Boston||Chicago||Wed, Feb 5 - Thu, Feb 6||$180|
|San Francisco||Chicago||Wed, Jan 8 - Sat, Jan 11||$276|
|Minneapolis||Chicago||Sat, Jan 11 - Sat, Feb 1||$72|
|Seattle||Chicago||Fri, Jan 10 - Fri, Jan 17||$198|
|Philadelphia||Chicago||Tue, Dec 17 - Thu, Jan 2||$292|
|Newark||Chicago||Fri, Jan 10 - Fri, Jan 17||$218|
|Portland||Chicago||Wed, Jan 8 - Tue, Jan 21||$178|
|Atlanta||Chicago||Tue, Jan 28 - Tue, Feb 4||$200|
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.