There's nothing better than driving through the streets of Chicago on a nice day; tree-lined streets, bustling neighborhoods, and incredible urban scenery around every corner. But Chicago is a vast metropolis with an endless array of streets, shops, and parks to explore. We recommend arriving with a game plan, or at least a trusty Getaround Guide to navigate the "Second City" with success.
First things first, you gotta get a car. Open your Getaround app, and find the perfect vehicle for your Chicago touring needs. Cruising down Michigan Ave? We might recommend a convertible. Heading out to lake country? Maybe try something with a bigger trunk. When you’ve got your wheels figured out, it's go time!
Here are a few places that really can’t be replicated anywhere else.
The Chicago Cubs were known up until a few years ago as the lovable losers, but their home stadium remained undefeated. Wrigley is a baseball mecca in the heart of the eponymous north-side neighborhood, Wrigleyville. Come a few hours before first pitch to soak in the best baseball block party in America and walk around "The Friendly Confines" for a great vibe and local color.
Right in the heart of the city is a green space filled with public art installations, home to dozens of festivals throughout the year, and a great jumping off place to wander through the entire downtown Loop. Come splash through Crown Fountain or take a funhouse selfie in Cloud Gate (aka The Bean). Yes, it’s touristy. But there’s a reason all the tourists are here. It’s beautiful.
Okay, you can’t actually enjoy these from your car. So, you’ll have to park it for a bit. (But, you can always rent a different car post-tour for a little variety.) However, the waterway tours through the city are not to be missed. No other city in America offers the same vantage point or gives the same reflection of history as a slow cruise past the Wrigley Building or any of the other towering Beaux Arts skyscrapers.
The Slightly Alternative
If you truly want to go like a local, here are a few places you might not see on the typical tours.
While the crowds herd toward lake shore, you might try heading to the West Side. This park is massive and can be reached via a 2.7 mile elevated abandoned railway path called the 606 urban hiking trail. Either pack a picnic or pop into one of the dozens of unique restaurants and bars along the way.
Old Town Ale House
Located in Old Town, directly across the street from famed Second City Theater, this dive bar is a beautiful microcosm of the city at large. Possibly the only place you’ll find tourists, young professionals, up-and-coming comedians, and octogenarians who’ve sat at the same stool since before you were born all shooting the breeze underneath some of the most interesting oil paintings you've ever seen.
Chicago may seem more like a comedy city, or a sausage city, but its music scene is not to be overlooked. Come to this well-stocked record store in Wicker Park and dig through crates upon crates of records while listening to perfectly-curated soundtracks from bands you wish you knew.
The Totally Off the Beaten Path
Want to show locals you know something they don’t? Pull up to these off-the-radar spots.
When people think Chicago, they think deep dish pizza. But what they should be thinking is tacos. Yes, tacos. This beloved Wicker Park-area spot has been pumping out the most mouth-wateringly delicious tacos since the mid-70’s. Pro-tip: Order a chili relleno on the side.
You know we got love for the South Side. We just try not to make too big a deal about it to keep the crowds away. So, we’ll keep one of our truly hidden gems down here. For simply one of the best views of the downtown skyline head to Promontory Point in Burnham Park. Just don’t tell too many people about where you snapped those incredible skyline pics.
This one’s purposely hidden, so we won’t say much. But after you’re done driving for the day, you might want to park somewhere near the Old Chicago Inn on Sheffield and Belmont. Down the alley to the left of the entrance there may or may not be a red-lit gate. If you follow that down to the end, there will be something very special waiting. If you know the password, that is.
Now that you’ve got your places to go, all you need is the car to get you there. We recommend finding one on the Getaround app. Just because Chicago is the land of the (hot) dogs, doesn't mean you have to wear yours out exploring the city.