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A cabin with table tennis at Camp Wandawega in Wisconsin.
A cabin with table tennis at Camp Wandawega in Wisconsin.
Camp Wandawega

Best places to stay on a Chicago road trip

The best hotels, motels, and B&Bs within driving distance of Chicago

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A cabin with table tennis at Camp Wandawega in Wisconsin.
| Camp Wandawega

Chicago and the surrounding area is famously flat as a pancake, but this doesn't mean that there's nothing to see on a road trip. There are many great destinations—and places to stay—that can be reached on a tank of gas from the Windy City. From contemporary highly-stylized campgrounds to refined bed and breakfasts to classic motor inns, we've taken a look around and piled a list that offers something for every budget.

Ready to get out of town for a weekend? Here's a handful of options to consider for your next road trip from Chicago. Did we miss your favorite spot? As always, the tip line and comment section are there for your suggestions.

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1. The American Club

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419 Highland Dr
Kohler, WI 53044
(800) 344-2838
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This small Wisconsin town is well known around the country for the faucet manufacturer that resides in it, but Kohler is also the home to the illustrious The American Club. A popular getaway and wedding venue for the well-to-do, this destination features several different lodging options, golfing, a full-service spa, and of course, fine dining.
The American Club

2. Washington House Inn

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W62N573 Washington Ave
Cedarburg, WI 53012
(262) 375-3550
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Cedarburg, Wisconsin is one of the state's most quaint and well-preserved towns, and for those seeking an old fashioned Midwestern experience, there's the Washington House Inn. Centrally located in Cedarburg, this old B&B is outfitted with cozy, though old school decor, and also offers a complimentary afternoon wine and cheese social hour.
Washington House Inn

3. The Brewhouse Inn & Suites

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1215 N 10th St
Milwaukee, WI 53205
(414) 810-3350
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Wisconsin is the land of cheese, brats, and beer, so what better way is there to spend your time in America's Dairyland than staying in the original Pabst brewery? Self-described as "post-Victorian steampunk meets urban-contemporary," the historic Brewhouse Inn & Suites factory building dates back to the mid-1800s as the Best & Company brewery. The hotel transformation of the old brewery was completed in 2013.

4. The Pfister Hotel

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424 E Wisconsin Ave
Milwaukee, WI 53202
(414) 273-8222
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Often lauded as one of the very best hotels in Milwaukee, the historic Pfister dates back to 1893 when Milwaukee was a major industrial hub in the Midwest. The hotel, which features a Romanesque Revival style design by the architect Charles Koch, is highly elaborate and ornate, but certainly within reach for travelers on any budget.
The Pfister Hotel

5. The Iron Horse Hotel

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500 W Florida St
Milwaukee, WI 53204
(888) 543-4766
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The Iron Horse is another unique industrial-to-hotel conversion in Milwaukee. While one may typically think of motorcycles when hearing the term "iron horse" (thanks Bon Jovi), the hotel—which was an industrial warehouse in a previous life—gets its name for being built near railroads. However, those interested in motorcycles won't be disappointed as the hotel is also closely located to the Harley-Davidson Museum.
The Iron Horse Hotel

6. Camp Wandawega

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W5453 Lake View Dr
Elkhorn, WI 53121
Perhaps the most Instagrammable place in the entire Midwest, this old campground was only just reimagined and revitalized in recent years. Outfitted with highly-stylized retro decor that's almost reminiscent of a Wes Anderson film, this old campground is a popular spot for weddings and even corporate retreats.

7. El Rancho Motel

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36355 Skokie Hwy
Gurnee, IL 60031
The old El Rancho Motel is certainly not your high-end motor inn, but it's one that film buffs may know well. The motel made a prominent cameo in the classic John Hughes comedy "Planes, Trains and Automobiles" featuring John Candy and Steve Martin. Don't expect anything extravagant here, but the motel, which has been renamed River Trail Gardens & Inn since the filming of the 1987 comedy, is certainly a fitting tribute for those seeking to pay homage to the late John Hughes or John Candy.
Paramount Pictures

8. Royal Victorian Manor

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344 Fremont St
Woodstock, IL 60098
(815) 308-5432
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Like the El Rancho Motel, the Royal Victorian Manor bed and breakfast in suburban Woodstock also has Hollywood pedigree. The old B&B was one of the main locations in the Harold Ramis comedy "Groundhog Day." Built in 1894, the old Victorian home didn't actually become a bed and breakfast until 2009, and in recent years, the house has bounced on and off the market. Earlier this year, the 6,000-square-foot property was seeking $645,000.

9. Felt Manor Guest House

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125 S Prospect St
Galena, IL 61036
(815) 777-9093
Located in historic Galena, Illinois, the Felt Manor Guest House is located in a historic Victorian mansion just blocks from downtown. The B&B has a classic, cozy feel and boasts a large parlor and front porch for relaxing and getting a sweeping view of the rolling hills surrounding Galena. In addition to breakfast, the Felt Manor also offers an afternoon wine tasting.

10. The Inn at Irwin Gardens

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608 5th St
Columbus, IN 47201
(812) 376-3663
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The small town of Columbus, Indiana is a must-stop for any architecture buff road tripping through the Midwest. In addition to its vast collection of groundbreaking modernist buildings, the town also boasts some fine lodging options, including the Inn at Irwin Gardens. Members of Columbus's prominent Irwin family owned and lived in the house for generations until being sold in 2009 to become a bed and breakfast and wedding venue.
Inn at Irwin Gardens

11. Beiger Mansion

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317 Lincolnway E
Mishawaka, IN 46544
(574) 256-0365
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This stately old mansion turned B&B is only a two-hour drive from Chicago. Completed in 1908, the column-flanked residence was built for Martin Beiger, an early industrialist and founder of the Mishawaka Woolen Company and Red Ball Band company. Similar to the gilded age mansions in the Chicago area, the grounds of this estate were designed by prominent landscape architect Jens Jensen. Today, the mansion serves as a bed and breakfast and popular wedding venue.
Beiger Mansion

12. Chestnut Street Inn

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301 E Chestnut St
Sheffield, IL 61361
(815) 454-2419
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This idyllic bed and breakfast ranks high with both guests and critics for its setting and for its food. This year, the Chestnut Street Inn received accolades from BedandBreakfast.com, winning a national breakfast contest with its savory Elvis Toast with Candied Bacon dish. Known for its savory cuisine, the Chestnut Street Inn also offers cooking classes.

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1. The American Club

419 Highland Dr, Kohler, WI 53044
The American Club
This small Wisconsin town is well known around the country for the faucet manufacturer that resides in it, but Kohler is also the home to the illustrious The American Club. A popular getaway and wedding venue for the well-to-do, this destination features several different lodging options, golfing, a full-service spa, and of course, fine dining.
419 Highland Dr
Kohler, WI 53044

2. Washington House Inn

W62N573 Washington Ave, Cedarburg, WI 53012
Washington House Inn
Cedarburg, Wisconsin is one of the state's most quaint and well-preserved towns, and for those seeking an old fashioned Midwestern experience, there's the Washington House Inn. Centrally located in Cedarburg, this old B&B is outfitted with cozy, though old school decor, and also offers a complimentary afternoon wine and cheese social hour.
W62N573 Washington Ave
Cedarburg, WI 53012

3. The Brewhouse Inn & Suites

1215 N 10th St, Milwaukee, WI 53205
Wisconsin is the land of cheese, brats, and beer, so what better way is there to spend your time in America's Dairyland than staying in the original Pabst brewery? Self-described as "post-Victorian steampunk meets urban-contemporary," the historic Brewhouse Inn & Suites factory building dates back to the mid-1800s as the Best & Company brewery. The hotel transformation of the old brewery was completed in 2013.
1215 N 10th St
Milwaukee, WI 53205

4. The Pfister Hotel

424 E Wisconsin Ave, Milwaukee, WI 53202
The Pfister Hotel
Often lauded as one of the very best hotels in Milwaukee, the historic Pfister dates back to 1893 when Milwaukee was a major industrial hub in the Midwest. The hotel, which features a Romanesque Revival style design by the architect Charles Koch, is highly elaborate and ornate, but certainly within reach for travelers on any budget.
424 E Wisconsin Ave
Milwaukee, WI 53202

5. The Iron Horse Hotel

500 W Florida St, Milwaukee, WI 53204
The Iron Horse Hotel
The Iron Horse is another unique industrial-to-hotel conversion in Milwaukee. While one may typically think of motorcycles when hearing the term "iron horse" (thanks Bon Jovi), the hotel—which was an industrial warehouse in a previous life—gets its name for being built near railroads. However, those interested in motorcycles won't be disappointed as the hotel is also closely located to the Harley-Davidson Museum.
500 W Florida St
Milwaukee, WI 53204

6. Camp Wandawega

W5453 Lake View Dr, Elkhorn, WI 53121
Perhaps the most Instagrammable place in the entire Midwest, this old campground was only just reimagined and revitalized in recent years. Outfitted with highly-stylized retro decor that's almost reminiscent of a Wes Anderson film, this old campground is a popular spot for weddings and even corporate retreats.
W5453 Lake View Dr
Elkhorn, WI 53121

7. El Rancho Motel

36355 Skokie Hwy, Gurnee, IL 60031
Paramount Pictures
The old El Rancho Motel is certainly not your high-end motor inn, but it's one that film buffs may know well. The motel made a prominent cameo in the classic John Hughes comedy "Planes, Trains and Automobiles" featuring John Candy and Steve Martin. Don't expect anything extravagant here, but the motel, which has been renamed River Trail Gardens & Inn since the filming of the 1987 comedy, is certainly a fitting tribute for those seeking to pay homage to the late John Hughes or John Candy.
36355 Skokie Hwy
Gurnee, IL 60031

8. Royal Victorian Manor

344 Fremont St, Woodstock, IL 60098
Like the El Rancho Motel, the Royal Victorian Manor bed and breakfast in suburban Woodstock also has Hollywood pedigree. The old B&B was one of the main locations in the Harold Ramis comedy "Groundhog Day." Built in 1894, the old Victorian home didn't actually become a bed and breakfast until 2009, and in recent years, the house has bounced on and off the market. Earlier this year, the 6,000-square-foot property was seeking $645,000.
344 Fremont St
Woodstock, IL 60098

9. Felt Manor Guest House

125 S Prospect St, Galena, IL 61036
Located in historic Galena, Illinois, the Felt Manor Guest House is located in a historic Victorian mansion just blocks from downtown. The B&B has a classic, cozy feel and boasts a large parlor and front porch for relaxing and getting a sweeping view of the rolling hills surrounding Galena. In addition to breakfast, the Felt Manor also offers an afternoon wine tasting.
125 S Prospect St
Galena, IL 61036

10. The Inn at Irwin Gardens

608 5th St, Columbus, IN 47201
Inn at Irwin Gardens
The small town of Columbus, Indiana is a must-stop for any architecture buff road tripping through the Midwest. In addition to its vast collection of groundbreaking modernist buildings, the town also boasts some fine lodging options, including the Inn at Irwin Gardens. Members of Columbus's prominent Irwin family owned and lived in the house for generations until being sold in 2009 to become a bed and breakfast and wedding venue.
608 5th St
Columbus, IN 47201

11. Beiger Mansion

317 Lincolnway E, Mishawaka, IN 46544
Beiger Mansion
This stately old mansion turned B&B is only a two-hour drive from Chicago. Completed in 1908, the column-flanked residence was built for Martin Beiger, an early industrialist and founder of the Mishawaka Woolen Company and Red Ball Band company. Similar to the gilded age mansions in the Chicago area, the grounds of this estate were designed by prominent landscape architect Jens Jensen. Today, the mansion serves as a bed and breakfast and popular wedding venue.
317 Lincolnway E
Mishawaka, IN 46544

12. Chestnut Street Inn

301 E Chestnut St, Sheffield, IL 61361
This idyllic bed and breakfast ranks high with both guests and critics for its setting and for its food. This year, the Chestnut Street Inn received accolades from BedandBreakfast.com, winning a national breakfast contest with its savory Elvis Toast with Candied Bacon dish. Known for its savory cuisine, the Chestnut Street Inn also offers cooking classes.
301 E Chestnut St
Sheffield, IL 61361