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Departure City: New York City

Destination: Chicago , IL

Dates: All Dates

Change your departure city  |  Modify your search  |  Package prices are based on double occupancy and include all tax recovery charge & service fees.

Destination Dates Price per Person
Chicago, IL
All Dates from $237
See options below

Available Dates

Destination Dates Price per Person
Chicago, IL
Thu, Feb, 11 - Sun, Feb 14 from $330
Chicago, IL
Fri, Feb, 12 - Sun, Feb 14 from $398
Chicago, IL
Sat, Feb, 13 - Mon, Feb 15 from $398
Destination This Weekend Price per Person
Chicago, IL
Leaving Thu, Feb 11
    Returning Sun, Feb 14
    Returning Mon, Feb 15
    Returning Tue, Feb 16

from $330
from $367
from $366
Chicago, IL
Leaving Fri, Feb 12
    Returning Sun, Feb 14
    Returning Mon, Feb 15
    Returning Tue, Feb 16

from $398
from $436
from $474
Chicago, IL
Leaving Sat, Feb 13
    Returning Mon, Feb 15
    Returning Tue, Feb 16

from $398
from $408
Destination Next Weekend Price per Person
Chicago, IL
Leaving Thu, Feb 18
    Returning Sun, Feb 21
    Returning Mon, Feb 22
    Returning Tue, Feb 23

from $299
from $289
from $282
Chicago, IL
Leaving Fri, Feb 19
    Returning Sun, Feb 21
    Returning Mon, Feb 22
    Returning Tue, Feb 23

from $294
from $266
from $259
Chicago, IL
Leaving Sat, Feb 20
    Returning Mon, Feb 22
    Returning Tue, Feb 23

from $244
from $237
Destination More Weekends Price per Person
Chicago, IL
Leaving Thu, Feb 25
    Returning Sun, Feb 28
    Returning Mon, Mar 1
    Returning Tue, Mar 2

from $299
from $334
from $364
Chicago, IL
Leaving Fri, Feb 26
    Returning Sun, Feb 28
    Returning Mon, Mar 1
    Returning Tue, Mar 2

from $264
from $299
from $330
Chicago, IL
Leaving Sat, Feb 27
    Returning Mon, Mar 1
    Returning Tue, Mar 2

from $264
from $288

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Nearby Destinations

Destination Dates Price per Person
Chicago Vicinity, IL
All Dates from $227
Chicago, IL
(includes luxury hotel)
All Dates from $259

Other Destinations in the Midwest

Destination Dates Price per Person
Akron/ Canton, OH
All Dates from $215
Milwaukee, WI
All Dates from $216
Indianapolis, IN
All Dates from $224
Cleveland, OH
All Dates from $235
Minneapolis/ St. Paul, MN
All Dates from $249
St. Louis, MO
All Dates from $250

Other Big City Destinations

Destination Dates Price per Person
Atlanta, GA
All Dates from $215
Dallas, TX
All Dates from $244
Houston, TX
All Dates from $253
Fort Worth, TX
All Dates from $261

Chicago: Why Go

Photo by Sherri Paul Photo by Sherri Paul
Chicago, IL: Our Kind of Town
Breeze into the Windy City, where you'll be blown away by a skyline of famous skyscrapers, miles of magnificent shopping, and nothing less than that spirited, Mid-Western charm.

Where the locals go: Chug an "Old Style" and bite into a hot dog while cheering the Cubbies at Wrigley Field, arguably the country's most charming ball park. Hard-core fans may sit in the bleachers in hopes of catching a homerun hit, but there's hardly a bad seat at the "Friendly Confines."

History lesson: Chicago is the birthplace of the modern skyscraper. Opt for the Chicago Architecture Foundation's River Cruise--touristy, but undoubtedly the most awe-inspiring perspective on everything from Art Deco masterpieces to Ludwig Mies van der Rohe's minimalism.

Did we mention it's free? From tropical skinks and salamanders to arctic penguins and polar bears, a visit to Lincoln Park Zoo is a crowd-pleaser. Open 365 days a year, this zoo, established in 1868, is among the nation's oldest.

Local flavor: You can't go wrong with porterhouse, rib-eye, or any other slab of meat at the original Mortons, the paradigm of Chicago-style steakhouses. And whether you take yours deep-dish or stuffed, you've got to try the "pot pie" pizza at Chicago Pizza & Oven Grinder.

As seen on TV: Channel John Belushi's short-order cook stint on SNL with a "Cheezburgah, Cheezburgah, Cheezburgah...," at the skit's inspiration, the Billy Goat Tavern, home to a killer double-cheeseburgah on a Kaiser roll.

The real deal: Lighten up at The Second City, the comedy club where the likes of Dan Aykroyd, Mike Myers, Bill Murray, and Chris Farley got their big breaks -- we think it's a national treasure, no joke.

Get your bearings: If you want to get around Chicago like a Chicagoan, get to know "the Loop" and "the L." Think: the Loop is the business district that is circled by the mass-transit, elevated train called the L (and the Chicago River).

Place we love, even if it's touristy: With 110 stories rising a quarter mile into the sky, the Sears Tower is the tallest building in North America. On a clear day you can see four states from the skydeck on the 103rd floor.

Where to blow a paycheck: Rain, snow, or shine, shopaholics flock to the Magnificent Mile, packed with department stores, boutiques, and specialty shops. Nearby on State Street is the historic, ornate Marshall Fields with a Tiffany ceiling and a lavishly decorated Great Tree during the holidays.

Editor's Chicago Picks

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