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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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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 $176
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 $181
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
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 $193
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 $200
per person
St. Louis, MO: Louie, Louie, We Gotta Go Now!
Find your thrill on Blueberry Hill, get your kicks on Route 66, have a lark in the footsteps of Lewis and Clark, march to the Arch, and feel the spirit of St. Louis.
Includes Flight, Hotel, Taxes & Fees
from $200
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
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 $204
per person
Canal at night
Photo by IgoUgo.com
Indianapolis, IN: More Than Just a Pit Stop
Hold on tight and enjoy the view because you don't want to miss Circle City's high-speed, heart-pumping attractions like the Motor Speedway and SportsZone.
Includes Flight, Hotel, Taxes & Fees
from $207
per person
Photo by IgoUgo.com
Cleveland, OH: So Rockin', It's Erie
With its Great Lakes location and Cuyahoga River Flats, Cleveland rocks everything from velvet-rope nightclubs to down-to-earth farmer's markets.
Includes Flight, Hotel, Taxes & Fees
from $208
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 $208
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
Cleveland Vicinity, OH: Buckeye Bonanza
Find all the charm of the northeast plus the walleye capital of the world in Cleveland's backyard.
Includes Flight, Hotel, Taxes & Fees
from $208
per person
Old Worthington
Photo by IgoUgo.com
Columbus, OH: More Than Meets the Buckeyes
Named for the man who led European expeditions to America, Columbus hosts a bevy of historical landmarks, plus a first-rate symphony, and the most spirited college football fans in the Midwest.
Includes Flight, Hotel, Taxes & Fees
from $211
per person
Rainbow over Niagara Falls
<br>Photo by IgoUgo.com
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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 $216
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 $216
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 $216
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 $216
per person
Green Bay, WI: Welcome to Packer Country
From the Lambeau Leap to tailgating in Titletown, Packer pride seeps from every corner of the Midwest's oldest settlement
Includes Flight, Hotel, Taxes & Fees
from $216
per person
Newark Vicinity, NJ: It's Not What You Think
Forget Bon Jovi, teased hair, and suped-up Camaros--New Jersey is as bucolic, cultured, and historic as New England.
Includes Flight, Hotel, Taxes & Fees
from $219
per person
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