Directions from Pittsburgh, Pennsylvania to Des Plaines, Illinois





UpTake Roadtrip Beta

We've selected a few points along the way for you to stop. We are trying to surface things you may not find elsewhere, but if we make some poor choices, please understand. Your feedback is appreciated.


Spring Meadow Farm Golf Course

Golf Courses – Middlebury, Indiana

Staff is friendly as well. More on golflink.com

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  • Meticulously maintained and constant investment by the owner will make this course one you'd wished you played. More on golflink.com

  • One of my favorites. The course looks like another ho hum North American effort at links style golf from the parking lot. But it doesn't take long to change your mind. The wind is apparently shippe... More on golflink.com

Shoreline Brewery

Breweries – Michigan City, Indiana

“Here at the Shoreline Brewery we pride ourselves in offering our customers the freshest menu possible, presented by a courteous, knowledgeable staff. Our beers are brewed with the freshest ingredi... More on BrewerySearch.com

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  • Shoreline Restaurant and Brew Pub is a brewery and family restaurant offering Casual Dining to the Northwest Indiana ... More on Shorelinebrewery.com

Eves Jazz and Stepin Club

Things To Do – Riverdale, Illinois

From the exterior you may get the impression that it is just another hole in the wall, but when you step inside this place puts you in mind of a elegant ... More on CitySearch

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  • This well decorated and designed club is outstanding. From the exterior you may get the impression that it is just another hole in the wall, ... More on CitySearch

Dairy Queen

Ice Cream – Geneva, Illinois

Yogi Bear Jellystone Park

Campgrounds – Portage, Indiana

They do not enforce their rules as people were partying, driving 4-Wheelers and Golf Carts, and dogs barking at 2 AM. More on CampRate.com

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  • This has to be the worst Jellystone I have ever stayed at. I was expecting many camping sites, but most (815 out of 926) were actually seasonal sites of which over half were run down and not taken ... More on CampRate.com

  • Dogs of all sizes are allowed. There are no additional pet fees. Dogs are not allowed in the rentals, must be leashed, and cleaned up after. This RV park is closed during the off-season. ... More on DogFriendly.com

Kelly Park

Parks – Chicago, Illinois

Category: Amusement/recreation Services Kelly Park is a great provider of family fun in Illinois. Visit us at our location ... More on localamusementparks.com

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  • Soon after World War II, the Chicago Park District and the Board of Education began providing cooperative programs in many of the city's rapidly growing neighborhoods. Known as the school-park plan... More on chicagoparkdistrict.com

Washington Park

Things To Do – Hammond, Indiana

Wales Bar

Bars – Toledo, Ohio

Big Chief Lounge

Bars – Chicago, Illinois

Big Chief Lounge - There’s not much to be said about the cocktails at Big Chief Lounge. They’re not necessarily cheap, but they’re as ... More on clubzone

Bridgeport Inn

Bars – Chicago, Illinois

This cozy, dark hole in the wall bar offers free darts, free pool , a good selection on the jukebox and in... More on CitySearch

4.0
1 review
1 source
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4.0 out of 5
1 review
1 source
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4.0
1+ reviews
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  • All of this nice and close to soutshside ballpark . More on CitySearch

  • This cozy, dark "hole in the wall" bar offers free darts, free pool, a good selection on the jukebox and in... More on CitySearch

Screwy Louie's

Things To Do – Kent, Ohio

Screwy Louie's - Why go to bed when you can have another drink? At Screwy Louie's, located at 200 S Depeyster St, the party marches into the late, late hours, as they have one of the best all-night parties. Of course, this ... More on clubzone

Italian Oven

Restaurants – Round Lake, Illinois

Ballo

Restaurants – Chicago, Illinois

The food is top notch. More on CitySearch

3.5
32 reviews
2 sources
Average Rating
3.5 out of 5
32 reviews
2 sources
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4.5
12+ reviews
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  • While the Mamas Meatballs are listed as an appetizer don't even think of going on to an entree unless you a... More on TripAdvisor

  • We were staying in the hampton inn and suites (which is conjoined to this restaurant) and decided, based on... More on CitySearch