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Chicago | Chicagoland | Northern | Central | Western | Southern | Southwest

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Hotels From
$99
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Big City Playground
Chicago, Family/Play
Families can play all day in Chicago. Discover rare treasures at the world-class Museum Campus. Lace up your skates and glide across the ice at Millennium Park’s outdoor rink. Spend your nights at a play, such as the family favorite Wicked.
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Hotels From
$99
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Chicago for Two
Chicago, Couples/Indulge/Discover
With its happening culture scene and critically acclaimed cuisine, Chicago makes for a great couples getaway. Stroll together through the halls of one of the world’s finest art museums.Indulge in five-star dining at an intimate restaurant. Browse the boutiques of big name designers. Applaud a play in one of Chicago’s historic downtown theaters. Relax and rekindle your romance with an extravagant spa day just for two.
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Hotels From
$60
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Winter Weekends
Chicagoland (Glenview, Schaumburg, Mount Prospect, Arlington Heights, Skokie, Evanston, Northbrook, Vernon Hills, Long Grove, Glenview, Lincolnshire, Buffalo Grove, Rolling Meadows), Family/Play/Discover
The suburbs that ring Chicago offer weekend fun for kids from big to small in your family. Take a tropical break at CoCo Key Indoor Water Resort. Catch a kid-friendly improv show. Cut the little ones loose at Kohl Children’s Museum.
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Hotels From
$95
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Winter Road Trip
Chicagoland (St. Charles, Geneva, Aurora, Lisle, Naperville, Oswego, Plano, Oak Brook, Oakbrook Terrace, Downers Grove, Lombard), Friends/Indulge/Explore
Gather your friends and take a road trip out to Chicago’s western suburbs. Here you can indulge yourselves at the European-style Herrington Inn & Spa or the popular Pheasant Run Resort & Spa. Shop in quaint historic towns and upscale malls. See a touring Broadway play or get your laughs at Zanies Comedy Club. Dine in restaurants on the picturesque Fox River waterfront. And make memories to last a lifetime.
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Hotels From
$55
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Rural Retreat
Northern (Galena, Elizabeth, Hanover, Scales Mound), Couples/Indulge/Discover/Explore
Galena is the perfect romantic retreat, nestled in the snow-covered hills of Northern Illinois. Spend time at a spa to gear up for a day of shopping on Main Street. Fly down the slopes of a leading Midwest ski resort, or join a bus tour to see over 3,000 eagles soaring in the wild. Tuck in for the night at a comfy bed and breakfast or enjoy the perks of an upscale resort.
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Hotels From
$102
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Snowy Sights
Northern (Utica, Ottawa, LaSalle), Family/Explore/Play
Families will find lots of winter fun in the Starved Rock area of Northern Illinois. Bundle up and take a hike to see sparkling ice falls. Discover one of the world’s largest assemblages of bald eagles as they soar along the Illinois River. Strap on a pair of cross-country skis or get revved for a snowmobile ride. Then again, you could ignore winter altogether and spend your days frolicking at an indoor water park resort.
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Hotels From
$53
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Make History
Central (Springfield, Petersburg), Couples/Friends/Discover
Get away to Springfield, where you’ll retrace the steps of Abraham Lincoln, one of the most beloved presidents in U.S. history. Tour the awe-inspiring presidential museum, see where the Lincolns lived and visit the tomb where they were laid to rest. Shop downtown, then see a play or groove to live jazz. Seek out fun Route 66 sites and snap a few pictures for your vacation memory book.

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Hotels From
$59
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Create Memories
Western (Peoria, East Peoria, Hanna City), Family/Play
It’s easy to create lasting memories in Peoria, a family-friendly town that’s even more welcoming in the winter. Spend time in the RiverFront district, where you’ll find abundant shopping and dining right on the Illinois River waterfront.

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Hotels From
$63
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Get Into the Outdoors
Western (Rock Island, Moline, East Moline, Savanna, Taylor Ridge), Couples/Explore/Discover
The Illinois half of the Quad Cities—Moline and Rock Island—offers plenty for the hearty winter outdoors enthusiast. Watch bald eagles soar over the Mississippi River. Ice skate at a picturesque riverside park. Ski or snowboard along the slopes of Ski Snowstar. Don’t leave without discovering two local legends: farming icon John Deere and a Native American warrior known as Black Hawk.

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Hotels From
$50
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Winter Romance
Southern (Carbondale, Du Quoin, Golconda, Metropolis, Alto Pass, Makanda, Cobden, De Soto, Pomona, Murphysboro, Carterville, Benton, Marion, Vienna, Whittington), Couples/Explore/Discover
You’ll be charmed by the romance of Southern Illinois, where the two of you can truly get away from it all. Spend the day sipping vintages along the Shawnee Hills Wine Trail. Hike the towering sandstone bluffs of the Garden of the Gods. Travel the Ohio River Scenic Byway that whisks you through the lush hills of the Shawnee National Forest. Buy a piece of Illinois artwork as a souvenir of your special trip taken together.
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Hotels From
$55
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Frosty Fun
Southwest (Alton, Grafton, Hartford, Hardin, Belleville, Carlyle Lake), Family/Explore
Head to the Southwest part of the state for family good times. Take an eagle-watching tour and spy majestic flocks of the wintering birds that nest in area cliffs. Play explorer at the Lewis & Clark Interpretive Center. Learn how to steer a barge at the National Great Rivers Museum.

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