Cheap Rental Car Deals in Chicago

Book Cheap Car Rentals in Chicago

When you get to the “Second City,” the first thing you’ll want to do is hit the gas on the Midwest-is-best good times. Because once you’ve gotten your car rental, Chicago better watch out— first-rate exploration is on. And with your own set of wheels, you have the freedom to see this Illinois superstar city from end to end.

Thanks to your Hotwire Hot Rate car rental deals, Chicago and all of its offerings are at your fingertips. That includes more pizza and Italian beef than you can shake a Chicago-style hot dog at. So make your last-minute getaway planning a breeze by taking a deep (dish) dive into these Windy City must-dos. Get ready to Chica-go.

Once you’re behind the wheel, where to next? Grab an iced coffee, because there’s a lot to cover.

Get a Second (City) Wind

You’re Trippin’: There are plenty of things to do within city limits to keep you busy for days on end, but one of the best parts of getting a Chicago car rental is the ability to hit the road and see what’s just outside Chicagoland. Start your road trips with a journey to Milwaukee (an hour and a half away) for some take-home six packs of brews and the finest Wisconsin cheese to charcuterie it up in your downtown Chicago hotel room. Or go Dutch in Holland, MI (2.5 hours away) and immerse yourself in over 4.5 million tulips in bloom all over the city during springtime visits. Lake Geneva is also an hour and a half away and is the number one vacay destination for Chicagoans, thanks to its walkable shoreline and eclectic eateries.

All Good in the Neighborhood: One of the best uses of your car rental in Chicago? Seeing some of the city’s 77 diverse neighborhoods. Start with Pilsen on the Southwest Side, voted Chicago’s coolest neighborhood, where you’ll find an incredible mix of Latinx history, art, and food. Try the city’s best Mexican cuisine at Taqueria Los Comales, around since 1973 and open 'til 1 a.m. Next, head to the hipster epicenter, Wicker Park, for all the artisanal food, drink, and brunch you can handle. More brunch (and nightlife) can be found in the city’s sanctioned LBTQ neighborhood, Boystown, also the perfect spot to grab a coffee at some of Chicago’s best coffee shops like Two Hearted Queen.

A River Runs Through It: Between Lake Michigan and the Chicago River, “water” the chances you’ll get a little boat time on your last-minute Windy City getaway? Pretty high (seas). The best way to take in the next-level architecture of the city is with a boat tour, which can be done via speed boat or aboard cruise boats complete with cash bars. If you haven’t gotten your sea legs, don’t feel left out—take a stroll on the Chicago Riverwalk instead, and peruse a collection of restaurants, bars, and views for days.

Shut Up and Drive: Taking a scenic car tour of Chicagoland is must-do once you’ve gotten your ride from one of the car rental places in Chicago. Cruising Lake Shore Drive is a staple, but why not take a gander at the greener side of the city? Chicago’s “Emerald Necklace” is a network of nearly 30 miles of interior streets that connect some of the most amazing (and lush) greenspaces in town, including Jackson and Humboldt parks.

Frequently Asked Questions About Chicago