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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

How to get last-minute hotel deals in Chicago?

After you’ve secured your Hotwire Hot Rate car rental, Chicago is your deep-dish pizza for the taking. But before you can truly serve up a good time, you’ve got to find last-minute hotels in Chicago for your getaway. And if you’re looking to stay on budget even on short notice, you don’t have to worry. When you book with Hotwire Hot Rate hotel deals, you can save an average of 60% versus booking a listed rate two weeks earlier. So locking down that 4-star hotel room at a 2-star price is a breeze, even in the Windy City.

Where is the car rental area at the Chicago airport?

When you’re looking to pick up your car rental, Chicago O’Hare is a likely spot to hop in your wheels. To get to the car rental offices to Chicago O’Hare, a shuttle ride is required. You can find the shuttle on at the lower level of the terminal near baggage claim, and follow the signs for pickup. When you get to the facility, you’ll find several companies available, including Enterprise car rental, Hertz car rental, and Budget rental cars. If you’re picking up your rental car at Chicago Midway, you’ll also need to take a shuttle. It can be found by exiting door number three near baggage claim.

How much are car rentals in Chicago?

When perusing car rental places in Chicago, you probably have money on your mind. That doesn’t mean you have to just grab any cheap car rental Chicago and hope for the best. When you reserve your ride with Hotwire Hot Rates, you can get way more than you bargained for. Even getting a luxury car rental in Chicago doesn’t have to be a dream—book a Hot Rate car and get high-end features for way less than you expected.

Is it safe to travel to Chicago during the coronavirus (COVID-19) crisis?

With recent COVID-19 closures and reopenings, you may be wondering is it safe to travel to Chicago right now. booking a last-minute trip to Chicago, make sure to check the most up-to-date information on safety measures, closures, and guidance on traveling during Coronavirus.

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*Savings are based on actual Hot Rate® car rentals made from airport pick-up locations as compared with the lowest published rates found on leading retail travel sites. Prices are dynamic and vary based on the booking date and length of the car rental. There is no guarantee these savings or rates will be in effect at the time of your search. Availability is limited. Hot Rate® cars are different from retail rates. With Hot Rate® cars you enter the location, date, and car class. The car rental company is revealed only after booking. All bookings are final.