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Departure City: Chicago

Destination: All Destinations

Dates: All Dates

Change your departure city  |  Start a new search  |  All prices are based on double occupancy.

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Hogback Bridge
<br>Photo by IgoUgo.com
Des Moines, IA: From 4-H to Four Star
This small town turned big city has blossomed into a versatile destination with enough charm to attract country bumpkins and urban hipsters alike.
Includes Flight, Hotel, Taxes & Fees
from $164
per person
Cincinnati Vicinity, OH: Wise Wanderings
You don't have to be a Rhodes Scholar to find your way to Oxford this weekend.
Includes Flight, Hotel, Taxes & Fees
from $165
per person
Minneapolis/St. Paul Vicinity, MN: Something Old, Something New
Old, new, borrowed and blue--you can find it all in Minnesota's friendly small towns.
Includes Flight, Hotel, Taxes & Fees
from $175
per person
Minneapolis/St. Paul, MN: Twin Cities' Double Feature
Okey dokey, oh yah, and you betcha: twin cities Minneapolis and St. Paul are like a two-for-one double feature. One offers sleek sophistication; the other offers down-to-earth sensibility.
Includes Flight, Hotel, Taxes & Fees
from $179
per person
Louisville
Photo by IgoUgo.com
Louisville, KY: Wax Nostalgic on the Banks of the Ohio
You won't be able to shrug that deja vu feeling in this historic city where the past is alive.
Includes Flight, Hotel, Taxes & Fees
from $192
per person
View from Mount Adams
Photo by IgoUgo.com
Cincinnati, OH: The Original Three Way
As the reigning Queen of the Midwest, Cincinnati boasts casinos that ride the river tide, amazing views that span three states, and the highest number of chili restaurants per capita in the country.
Includes Flight, Hotel, Taxes & Fees
from $194
per person
Naples/Gulf Coast, FL (via Fort Myers): Florida's Riviera
More sophisticated than Florida's trendy east coast, Naples, and the diverse stretch of beaches surrounding it, please sunbathers, small tykes, and shoppers alike.
Includes Flight, Hotel, Taxes & Fees
from $201
per person
Fort Myers
Photo by IgoUgo.com
Fort Myers, FL: A Timeless Classic
It's what epic movies are made of, the stuff of Southern mansions and stately palms--and a river runs through it.
Includes Flight, Hotel, Taxes & Fees
from $201
per person
Roman God Photo by IgoUgo.com
Kansas City, MO: Bebop 'Till Ya Don't Stop
The land of BBQ. The birthplace of Bebop. The City of Fountains. In this city of many hats, there's a lot more to keep you entertained than you might think.
Includes Flight, Hotel, Taxes & Fees
from $202
per person
Omaha, NE: Steaks Are High
Birthplace to Fred Astaire, ballyhooed home to the College World Series, and mushrooming with Missouri Riverfront shops--discover why Omaha is much more than a meat-eater's paradise.
Includes Flight, Hotel, Taxes & Fees
from $206
per person
Detroit Vicinity, MI: Inspiration for Innovation
There must be something in the Detroit River water, because the towns around Detroit have long been home to groundbreaking art and invention.
Includes Flight, Hotel, Taxes & Fees
from $208
per person
Sanibel and Captiva Islands, FL (via Fort Myers): Sixty Shades of Sea Shells
Capture someone's heart on these serene islands off Florida's Gulf coast.
Includes Flight, Hotel, Taxes & Fees
from $219
per person
Pittsburgh Vicinity, PA: It's A Wonderful Life in Steel Country
Steel yourself away to the Burgh's burroughs and beyond for art, architecture, and adventure.
Includes Flight, Hotel, Taxes & Fees
from $219
per person
Rainbow over Niagara Falls
<br>Photo by IgoUgo.com
<br>
Buffalo/Niagara Falls, NY: The Rainbow Connection
This honeymoon hotspot is not just for lovers and dreamers. The larger-than-life falls, scenic hiking areas, vineyards, and tasty treats will melt even the coldest of hearts.
Includes Flight, Hotel, Taxes & Fees
from $220
per person
Wilmington, DE (via Philadelphia): As Distinguished as a Du Pont, As Winsome as a Wyeth
Spend the weekend in the stomping grounds of two of America's most prominent families.
Includes Flight, Hotel, Taxes & Fees
from $224
per person
Photo by Lisa Van Bockstaele
Niagara Falls, NY (via Buffalo): The Rainbow Connection
This honeymoon hotspot is not just for lovers and dreamers. The larger-than-life falls, scenic hiking areas, vineyards, and tasty treats will melt even the coldest of hearts.
Includes Flight, Hotel, Taxes & Fees
from $225
per person
Pittsburgh, PA: A Confluence of Culture
Once known as the home of "Big Steel," Pittsburgh has reemerged as a city where modern art, fine dining, and three rivers merge to form one well-rounded cultural experience.
Includes Flight, Hotel, Taxes & Fees
from $225
per person
Photo by Jeff Schwartzenberg
Nashville, TN: Grand Ole Opry-tunities
From jubilant jug bands to the likes of Lyle Lovett, Tennessee's rolling Cumberland River hills are alive with the boogie-sweet sound of music.
Includes Flight, Hotel, Taxes & Fees
from $226
per person
Orlando, FL: This Land is Your Land-o
From rollercoaster forest to gulf-stream waterslide, Orlando was made for you and me. Come live out your food fantasies, and indulge your sense of wonder in the theme park capital of the world.
Includes Flight, Hotel, Taxes & Fees
from $226
per person
St. Petersburg/ Clearwater, FL (via Tampa): Bronze Bods and Gods
Pump up your body with a jog on the beach, then please your soul viewing gilded sculptures from 795 B.C.
Includes Flight, Hotel, Taxes & Fees
from $228
per person
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