DriveShare Chicago: Travel Guide

The Windy City. Home to the Bulls, Bears, Cubs, Sox and Hawks, iconic hot dogs and an even more iconic skyline, plus plenty of Italian beef and beer. You know what goes great with all of those things? An awesome DriveShare car to get you from stadium to stadium, from taco stand to brewery, from the North Side through the Loop down to the South Side and back. 

Chicago streets can be a bit intimidating – try navigating a car through the Loop at 5pm and you know what we mean – but we’ve also got the best places for you to head to behind the wheel of your new DriveShare vehicle. 

To help you enjoy the drive, set the GPS for these great cruising destinations around Chi-town and even beyond the city limits for some great Chicago-area attractions. Let’s hit the road on this Chicago travel guide!

Chicago Travel Guide
Photo: Wikipedia commons

See The Skyline

If you started and ended your DriveShare cruise just on Lake Shore Drive, honestly, you could probably call it quits after that and feel complete. From the Museum of Science and Industry in Hyde Park, all the way up to Hollywood Avenue in Edgewater, this stretch of pavement packs in more sights per square inch than most roads do in a mile.

Lake Shore Drive not only has the benefit of the world’s greatest skyline to the west, but also a massive lake to the east (hence the name). In one direction you’re looking at soaring steel, concrete and glass, and in the other direction, nothing but glittering water and waves. It’s beautiful during the day, and occasionally almost overwhelming at night. 

If you start down by the 63rd Street Beach just south of the Museum of Science and Industry and drive north, you’ll pass right by legendary destinations like Soldier Field, the Field Museum, Grant Park, Buckingham Fountain, Navy Pier, Oak Street Beach, Lincoln Park, and more. Beyond those immediate highlights, you’ll see the full stretch of the skyline from the South Loop to Streeterville and River North to the condo high-rises of Lakeview, Uptown and Edgewater. As soon as it’s over you’ll want to turn around and do it again. 

Great news – you can.

Chicago Travel Guide
Photo: Alyssa Black

Marvel at the Mag Mile & Meander Down Michigan 

On the way back south we’d suggest getting off of Lake Shore Drive right at the apex of the Magnificent Mile. North Michigan Avenue all the way down to the river is perhaps the most famous street-level stretch of avenue in America and it’s an epic – if often quite crowded – drive in between luxe boutiques, fancy hotels, soaring high-rises and architectural masterpieces. At the end of the Mag Mile, you’ll be right on the Chicago River where they dye it green each St. Patrick’s Day.

Further south of the river remains Michigan Avenue but you leave the “Mag Mile” portion in the rearview. Still, we’d recommend continuing the cruise south to take in even more spectacular skyrise sights, views of Millennium Park and the famed reflective Cloud Gate sculpture (aka “The Bean”) followed by the Art Museum. 

Chicago Travel guide

For a great photoshoot location, hop over to the parking lot near the Adler Planetarium where Grant Park and the skyline make an amazing panorama for your DriveShare shots. Keep heading south on Michigan and you’ll even get into historic Motor Row and the convention center area, but we’d have you hop back onto Lake Shore and head north so you can…

Wind Beneath Wacker Drive

When a city has a very specific subterranean stretch of road made famous in not just one film but two (The Blues Brothers and The Dark Knight), well, it may not be the most scenic way to get through the city but it’s something that has to be driven to be experienced. You can access Lower Wacker Drive from Lake Shore Drive near Navy Pier, and it will curve you beneath the Loop along the Chicago River until you pop out by the Willis Tower. And yes, you want to take Lower Wacker. The drive along Upper Wacker is fine, but we have other ways of getting you through the Loop. 

Along the way you’ll see … well, a lot of concrete, really, with glimpses of the river and other downtown side streets along the way. But it’s worth the adventure to get down there and feel like you’ve really been in the heart of the city. From here you can hop on the Eisenhower Expressway for a trip to the ‘burbs, but we’d say head back downtown to take in one of the world’s most famous downtown areas:

Live It Up In The Loop

When you emerge from Lower Wacker Drive, just take a second to look up and around – you’ll probably be able to see tourists standing on the ledges protruding from the Willis Tower Skydeck. (It’s the tallest building in the hemisphere; it’s hard to miss.) From this point in the southwest corner of the Loop, you can basically zig-zag in any direction and find yourself in front of a famous building or business. 

Time it right on an early weekend morning when any stubborn office workers are at home and you can pretty much have the streets to yourselves. That’s when we’d recommend taking your own self-guided tour to find places like Macy’s at Marshall Fields, the Chicago Theater, the Berghoff Restaurant, Daley Plaza and the famed Picasso statue (again, where the Blues Brothers abandoned their famed Bluesmobile) as well as City Hall, the Palmer House Hilton and looking across the river, the Merchandise Mart. 

You should definitely drop a pin at Jackson and Michigan where you’ll be able to…

Set Out On the Mother Road (Shortly) 

This is where the legendary Route 66 began, as did so many trips west to Los Angeles. The famous Mother Road crossed over half the country before the interstate system was built, and spanned about 2,500 miles. Much of it is gone now, but you can still start a drive from here at the apex point, and follow the original route for a while through town and into the suburbs. 

While much of the current Route extends into strip malls and sprawl eventually, we do strongly recommend stopping for breakfast at the famed Lou Mitchell’s, which opened in 1923 on the original Route 66 route and has been slinging eggs, bacon and coffee ever since. It’s a legit classic, and it’s usually got the lines to prove it. (For some heartier lunch fare, Manny’s Deli is a short drive south where a pastrami or corned beef sandwich is worth the detour. And always add a latke.)

Chicago Travel Guide

Looking for more Mother Road destinations? Head to Texas for a DriveShare experience, where we’ve got more Route 66 sights to suggest there too. 

If these routes have inspired you to take a drive but you need a suitably classic car to cruise these highways and byways? Get started at Hagerty DriveShare, then get ready to fire up the engine and hit the road. 

And if you love your DriveShare so much you decide to acquire a collectible car, make a point to check out Hagerty Garage and Social: one part premiere classic car storage, one part car-lover’s community.


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