Car Rental in Chicago

Chicago, as the third most popular city in the United States, is a bustling metropolis with a dense downtown core at its heart. The city offers almost anything a traveler might have on his to-do list. This includes world-class museums, exhibitions of the finest artworks, an unending supply of entertainment possibilities, and a plethora of dining options. 

With crowded traffic and pricey parking in the downtown core, it may seem unwise to rent a car to visit Chicago. However, destinations in the surrounding suburbs and further afield are best reached with your own vehicle. It is not much of a surprise, therefore, that Chicago is Discover Car Hire’s third most popular rental destination. 

• From Chicago to Los Angeles - 65 offers from $106.69 per day
• From Chicago to San Francisco - 39 offers from $107.83 per day
• From Chicago to New York - 27 offers from $82.75 per day
• From Chicago to Denver - 39 offers from $83.74 per day
• From Chicago to Orlando - 39 offers from $105.84 per day

• O’Hare International Airport - Most travelers will arrive at O’Hare, one of the busiest airports in the country. Unfortunately, the rental desks at O’Hare are disjoint and travelers must find the shuttle bus of their specific agency to get to their pick-up point. 
• Midway Airport - Closer to Downtown, Midway mostly serves low-cost airlines airline in addition to some other domestic flights. Unlike at O’Hare, all of the rental desks are conveniently located together here with a joint shuttle bringing you to them.
• Union Station - Those traveling by train with Amtrak arrive at Union Station, from which most downtown rental locations are within convenient reach.

The Windy City, as Chicago is known as, is actually only slightly windier than the average American city. The city has four distinct seasons, from hot summers to cold, somewhat snowy winters and pleasant springs and falls in between.

From street food to Michelin-starred restaurants, no traveler will remain hungry for very long. Of particular culinary note is Chicago’s famous deep-dish pizza. The polar opposite of thin-crust pizza, deep-dish is baked in a round pan and loaded with toppings and tomato sauce. 

Historically, Chicago was known for its music scene. Poor black workers from the South migrated to the northern cities during the first half of the twentieth century, bringing with them their music of blues and jazz. Musicians such as Muddy Waters led the development of the Chicago Blues which is still popular today with the city hosting the annual Chicago Blues Festival.In turn, jazz musicians brought Dixieland jazz from New Orleans and developed it into a unique Chicago Style.In the early 80s, underground DJs developed house music. Immensely influential for many popular musicians, house continues to have a wide following both in popular music and underground. 

Chicago, having at least one franchise in every American sports league, is a sports mecca. The city is split in half when it comes to baseball, with residents on the South Side being loyal to the White Sox and those on the North Side, the Cubs. In basketball, the Bulls are known for their historic run of six championships in the 1990s while being lead by Michael Jordan. The Blackhawks, one of the original professional hockey teams in America, continue to perform at a high level on the ice. And finally, the city becomes engrossed with Bears of the National Football League in the fall.

• Navy Pier - Chicago’s most popular tourist attraction, Navy Pier, is packed with options for dining, shopping, relaxing in the parks and gardens, family entertainment and viewing world-class exhibitions. No trip to Chicago is complete without riding its Centennial Wheel. 
• Skydeck at Willis Tower - Still known by many as the Sears Tower, Willis Tower is the second tallest building in the Western Hemisphere after One World Trade Center in New York City. Take a trip to the 103rd-floor observation deck where you can stand on glass and look straight down at the street from 1,353 feet (412m) or peer out at the vast waters of Lake Michigan or endless miles of plains.
• 360 Observation Deck at John Hancock Center - A less crowded alternative to the Willis Tower, the John Hancock Center has an observation deck on the 93rd floor some 1,00 feet (300m) above street-level. Great views of Lake Michigan are supplemented with an attraction called Tilt, where the floor tilts 30 degrees leading to views look straight down at Michigan Avenue. 
• Lake Shore Drive - This drive between the skyscrapers and Lake Michigan will take you past The Adler Planetarium, Navy Pier, The Field Museum, Shedd Aquarium, the Art Institute of Chicago and Lincoln Zoo. 
• Oak Park - Frank Llyod Wright began his career in this suburban village just west of Chicago. Travelers can find various buildings designed by the famous architect, including the Frank Llyod Wright Home and Museum, along with the birthplace home and associated museum of author Ernest Hemmingway. 
• Chicago History Museum. Open since the 1850s, this North Side Museum in Lincoln Park is one of the oldest — and most interesting — in Chicago. Although the museum’s earliest artifacts perished in the Great Chicago Fire, there are plenty of interesting exhibits and collections on all things Chicago. In addition to permanent exhibitions, the museum frequently hosts various cultural events. Visit its official website to learn more.

From $6.50 in the Loop to $2 in neighborhoods outside of the Central Business District. pay with either coins (usually only quarters, 25 cent coins, are accepted) or credit cards. Be sure to display the receipt on the dashboard inside your vehicle.

Parking garage rates vary throughout the city. There are apps where it is possible to reserve a parking spot in one, often at a discounted rate. Be sure to also confirm parking rates at your chosen hotels, as most will not have free parking, particularly in or near downtown. 

The Chicagoland area has several Interstate highways that are tolled, including portions of I-88, I-90,I-294, I-355 and IL-390. In addition, there is a connection between the northwest border of Indiana and the center of Chicago via a bridge known as the Chicago Skyway.

Tolls can be paid with either an I-Pass transponder or cash. Depending on your rental car provider, your vehicle may come equipped with an I-Pass transponder. While it is the most convenient method of payment, not requiring you to stop at a toll booth, your rental car provider will charge a convenience fee for its use (usually per day, starting from the first day that it is used). It may, therefore, be preferable to make payments with cash, in which case be sure to remain in the right lanes approaching the toll booths. At the toll booths of the Chicago Skyway, drivers may also pay with a credit card.

• Galena - Located about 160 miles west of Chicago, Galena is a quaint historical town with more than a thousand buildings on the National Historic Register.  Is rich history has been preserved, with many of its historic buildings open for tours. 
• Springfield - No, you won’t find Moe’s Tavern, the Kwik-E-Mart, or a nuclear power plant here. Instead, the capital of Illinois offers travelers an extensive history lesson based primarily on one of America’s greatest presidents, Abraham Lincoln. If one has his fill of Lincoln, the city is also home to the Dana-Thomas House, designed by Frank Lloyd Wright and including furniture designed by him. 
• Six Flags Great America - Open from the summer months through Halloween, and since 2018 for Christmas Season, this Six Flags location is the largest theme park in Illinois. Its location in roughly halfway between Chicago and Milwaukee makes it within easy reach of Downtown Chicago by car. Enjoy the exhilarating experience of the 16 roller coasters, cool off in the hot summer weather at the attached water park, or be horrified during Fright Fest. 
• Lake Geneva - Travel north just across the Wisconsin border to find this popular area for Chicago vacationers. Among typical lake activities, it is possible to hike the 20 miles around the lake on a public footpath. 
• Ravina Festival - Venture out of the city to the summer residence of the Chicago Symphony Orchestra. This concert venue also hosts various other concerts throughout the summer. 
• Oglesby - Near Oglesby, around two hours west of Chicago, are Matthiessen and Starved Rock State Parks, the latter of which is the most visited state park in Illinois.  The parks offer numerous opportunities for outdoor adventures, from hiking and camping to boating and fishing.
• Starved Rock State Park. Known for its river valleys, canyons, and stone formations, Starved Rock is one of the most interesting protected areas in Illinois. There are numerous indigenous archaeological sites, as well as a variety of flora and fauna. Located 93 miles (150 km) southwest of Chicago, Starved Rock can be reached by car in about 90 minutes and, therefore, can be easily visited on a day trip, but if you’re not in a rush, there are a number of historical lodges inside the park where you can stay. 

Renters in Chicago prefer intermediate SUVs, such as the Nissan Rogue the most, followed by intermediate cars, like the Toyota Corolla, and full size SUVs, like the Jeep Cherokee. During winter, renters should be sure that their rental vehicles are able to safely handle snowy driving conditions. 

Note that some rental companies have specific restrictions on where their rental cars can be driven. This includes Fox and Sixt which only allow their cars to be taken to states which immediately border Illinois (i.e., Wisconsin, Iowa, Missouri, Kentucky, and Indiana. While Routes allows renters to travel to any state, it requires renters to notify the company in advance and limits the daily mileage allowance to 200 miles per day. 

All other rental companies not mentioned above allow their cars to travel to any state and also to Canada. 

• St. Louis, MO - The Gateway to the West lies a few hours drive southwest of Chicago. Millions visit every year to absorb the views of the Mississippi River from atop the Gateway Arch. Then they stick around for tours of one of the largest breweries in the world, that of Anheuser-Busch, with its included tasting and famous Clydesdale horses.
• Milwaukee, WI - Once the brewing capital of the world, Milwaukee now bills itself as the city of festivals. One of the city’s festivals, Summer Fest, is deemed by some to be the largest music festival in the world. In the unlikely event you were to travel to Milwaukee when a festival is not taking place, the city hosts numerous other attractions for the eager traveler. 
• Madison, WI - The capital of Wisconsin is an easy day’s drive to the northwest of Chicago. Surrounded by five lakes, Madison has numerous opportunities for dining, shopping, and entertainment. It is situated at the heart of a vast rural area waiting for exploration. 
• Indianapolis, IN - Located smack dab in the middle of the state of Indiana and less than 200 miles south of Chicago, Indianapolis is the metropolis of Indiana.
• Detroit, MI - A few hours drive east on I-94 brings travelers to Detroit, with its storied music scene, much like Chicago. Once the automobile capital of the world, Detroit now has a reputation of being a shell of its former self. In recent years, however, its downtown core has been revitalized with new attractions and renovated historic buildings and now offers travelers a great experience.