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Presenting the Curbed Chicago Regional Getaways Map

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Greetings all you city-weary folk! There comes a time when most of us high-strung, light-sleeping urbanites require a long weekend just roughing it— even in late fall/early winter. The Prairie might not be the beacon for naturalist explorers that the Rockies or Coastal Maine is, but it does offer water, woods, and recreation all within a few hours drive of Chicago. Curbed scrolled through the vacation rentals of Home Away to bring you 13 delightful options, conveniently mapped below. Bear in mind this is just a sampling, albeit based on highest-rated properties. Also, some addresses are approximate. Enjoy!

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Eater maps are curated by editors and aim to reflect a diversity of neighborhoods, cuisines, and prices. Learn more about our editorial process.

Galena Town Home

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Size: 2/2, sleeps 4-6Amenities: Game room, small snack bar, large pool and deck area, tennis courts, adjacent golf course and lake, horseback riding.Price: Not listed

Galena Vacation House

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Size: 4/3.5, sleeps 10Amenities: Access to Territory Owners Club with indoor pool and fitness center. Also close to Lake Galena, skiing, and historic downtown Galena. Home includes hot tub, grill, and fireplace.

Home On the Fox River

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Size: 3/3, sleeps 12Amenities: The Fox River provides the obvious in fishing and boating. House is equipped with sauna, outdoor hot tub, fireplace, home theater, and fitness machines.Price: $150-$275/night; $900-$1500/week

Central Illinois Country Retreat

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Size: 2/1, sleeps 6Amenities: This one is for the manly type-- hiking, hunting, trapping, hand-pumping your water, etc. But the house itself has a very attractive old porch and rustic allure.Price: Not specified

The Davis House, Glen Ellyn

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Size: 4/2.5, sleeps 9Amenities: Historic setting in old Victorian home on a cul-de-sac amongst other historic properties. Home features fireplace, large flat screen TV, gourmet kitchen, and library. Short distance to downtown Glen Ellyn.Price: $245-$295/night; $1495-$1795/week

Lake of Egypt Cottage

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Size: 3/2, sleep 7Amenities: This is a whole 'nuther part of Illinois, south of St. Louis. If you're passing through or craving certain backwoods qualities, this lakefront A-frame oughta do nicely. It's got fishing, boating, hiking, skiing, mountain biking, and wineries all close-by.Price: Not indicated

Lighthouse Cove Condo

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Size: 1/1, sleeps 4Amenties: Plenty of scrumptious stuff in this resort complex, like pools, hot tubs, and wood-burning fireplace. Two ski slopes, spa, and casino are nearby.Price: $140-$190/night

StaySpa on Castle Rock Lake

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Size: 4/4, sleeps 12-14Amenities: This place has full-on spa accouterments from massage chairs to hot tubs and cold plunges. Snowmobile trails run through the property, and all the spoils of Wisconsin Dells are nearby.Price: $595-$895/night; $3800-$4500/week

Lake Sinissippi Woodsy Cabin

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Size: 2/1, sleeps 4Amenities: Sparse, though the lodging looks quite comfortable This place is all about woodsy anonymity and wildlife.Price: $125-$200/night; $750/week

Cedar Grove Lakefront House

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Size: 6/5.5, sleeps 12Amenities: Another option for large-scale retreats, this 6,000-square-foot home sits has private beach frontage on Lake Michigan. 15' ceilings, huge deck, basketball court, and optional concierge service greet vacationers.Price: $1000-$1500/night; $4000-$6750/week

"The Miami" at Sheridan Beach

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Size: 1/2, sleeps 4Amenities: "The Miami" is pretty much just that-- an extravagant beachfront property with jumbo terraces set behind the dunes. Rental includes outdoor hot tub, indoor jacuzzi, steam room, and fireplace.Price: $1400/week

The Silver Heron

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Size: 4/5, sleeps 12Amenities: A short ways down the shore from The Miami is The Silver Heron, a more contemporary piece of resort-y architecture. The home is on a bluff and comes with 20' ceilings, a multitude of terraces, pool table, spa, and a couple of fireplace.Price: Not indicated

Irish Haven

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Size: 4/3.5, sleeps 8-12Amenities: Thinking of orchestrating a big Norte Dame football pilgrimage? Here's a fine old home that can make it happen. Just a mile from campus, the house offers game room, fireplaces, TVs in nearly every room, and wi-fi.Price: Not indicated

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Galena Town Home

Size: 2/2, sleeps 4-6Amenities: Game room, small snack bar, large pool and deck area, tennis courts, adjacent golf course and lake, horseback riding.Price: Not listed

Galena Vacation House

Size: 4/3.5, sleeps 10Amenities: Access to Territory Owners Club with indoor pool and fitness center. Also close to Lake Galena, skiing, and historic downtown Galena. Home includes hot tub, grill, and fireplace.

Home On the Fox River

Size: 3/3, sleeps 12Amenities: The Fox River provides the obvious in fishing and boating. House is equipped with sauna, outdoor hot tub, fireplace, home theater, and fitness machines.Price: $150-$275/night; $900-$1500/week

Central Illinois Country Retreat

Size: 2/1, sleeps 6Amenities: This one is for the manly type-- hiking, hunting, trapping, hand-pumping your water, etc. But the house itself has a very attractive old porch and rustic allure.Price: Not specified

The Davis House, Glen Ellyn

Size: 4/2.5, sleeps 9Amenities: Historic setting in old Victorian home on a cul-de-sac amongst other historic properties. Home features fireplace, large flat screen TV, gourmet kitchen, and library. Short distance to downtown Glen Ellyn.Price: $245-$295/night; $1495-$1795/week

Lake of Egypt Cottage

Size: 3/2, sleep 7Amenities: This is a whole 'nuther part of Illinois, south of St. Louis. If you're passing through or craving certain backwoods qualities, this lakefront A-frame oughta do nicely. It's got fishing, boating, hiking, skiing, mountain biking, and wineries all close-by.Price: Not indicated

Lighthouse Cove Condo

Size: 1/1, sleeps 4Amenties: Plenty of scrumptious stuff in this resort complex, like pools, hot tubs, and wood-burning fireplace. Two ski slopes, spa, and casino are nearby.Price: $140-$190/night

StaySpa on Castle Rock Lake

Size: 4/4, sleeps 12-14Amenities: This place has full-on spa accouterments from massage chairs to hot tubs and cold plunges. Snowmobile trails run through the property, and all the spoils of Wisconsin Dells are nearby.Price: $595-$895/night; $3800-$4500/week

Lake Sinissippi Woodsy Cabin

Size: 2/1, sleeps 4Amenities: Sparse, though the lodging looks quite comfortable This place is all about woodsy anonymity and wildlife.Price: $125-$200/night; $750/week

Cedar Grove Lakefront House

Size: 6/5.5, sleeps 12Amenities: Another option for large-scale retreats, this 6,000-square-foot home sits has private beach frontage on Lake Michigan. 15' ceilings, huge deck, basketball court, and optional concierge service greet vacationers.Price: $1000-$1500/night; $4000-$6750/week

"The Miami" at Sheridan Beach

Size: 1/2, sleeps 4Amenities: "The Miami" is pretty much just that-- an extravagant beachfront property with jumbo terraces set behind the dunes. Rental includes outdoor hot tub, indoor jacuzzi, steam room, and fireplace.Price: $1400/week

The Silver Heron

Size: 4/5, sleeps 12Amenities: A short ways down the shore from The Miami is The Silver Heron, a more contemporary piece of resort-y architecture. The home is on a bluff and comes with 20' ceilings, a multitude of terraces, pool table, spa, and a couple of fireplace.Price: Not indicated

Irish Haven

Size: 4/3.5, sleeps 8-12Amenities: Thinking of orchestrating a big Norte Dame football pilgrimage? Here's a fine old home that can make it happen. Just a mile from campus, the house offers game room, fireplaces, TVs in nearly every room, and wi-fi.Price: Not indicated