Rent and Save
$15 Off Base Rate of $175 or MoreReserve a rental car and save $15 off base rate (time and mileage) of $175 or more. Terms Apply.
Most Popular
Free Rental Car UpgradeEnjoy a free one-car class upgrade on your next car rental of an economy, compact, intermediate, midsize or standard size car. Terms Apply.
Last Minute Deal
Last Minute SpecialsCheck out great last minute car rental specials from Alamo for daily and weekly rentals in the U.S and Canada.
Book Early Deal
Plan Ahead SpecialsBook your next rental car in advance with Plan Ahead Specials and save money on rentals in the U.S and Canada.
Welcome to Chicago! This iconic Midwestern city is a great travel destination for your family. Whether you want to experience some of the best shopping in the nation or you're dying to go on an adventure, you'll find something in or near Chi-Town to suit your tastes.
Chicago offers a rich range of activities to keep you and your family busy.
Take the family to Navy Pier, one of the city's top attractions. This waterfront playground of wonders can easily take up an entire day of your vacation. It consists of 50 acres of museums, restaurants, rides, shops, and more. For a brilliant view, take a ride on the Ferris wheel, which is 150 feet tall. You'll be able to take in the city skyline and the mighty Lake Michigan. Be sure to let the kids take a ride on the carousel. Navy Pier is also home to numerous events throughout the year, so be sure to check out its events calendar before you book your vacation.
Millennium Park is another can't-miss family attraction in Chi-Town. This 25-acre park in downtown is where you'll find the famous Cloud Gate sculpture, which is more famously known as "the Bean." Throughout the park, there is even more exciting art. Stroll through Lurie Garden, and if you visit in the winter, go ice skating. During warmer weather, head there to check out a live performance.
Love to shop? You'll never want to leave the Magnificent Mile, often called "the Mag Mile." This famed stretch of Michigan Avenue boasts more than 460 retail shops. Buy some nice clothes, feast on gourmet food, and pick up some amazing handbags and accessories. Or, you can simply take a walk. There are about 50 landmark structures along the Mag Mile — can you say "photo ops?"
Get in touch with your cultured side when you visit the Art Institute of Chicago. You could spend years becoming familiar with all of the creative brilliance contained in this building. The institute owns more than 300,000 pieces of art! Be sure to check out the Modern Wing, which houses the institute's design and architecture collection. Tickets to the institute are affordable, but you can save even more if you buy a Chicago CityPass.
If you want to step away from the hustle and bustle of Chicago for a day, hop in your rental car and head out of the city.
If you love the outdoors, take the hour-and-a-half drive to Oglesby, Illinois for your day trip. At the Vermillion River, you'll find the best rafting opportunity within a reasonable distance of Chicago. Spend a few hours on the water to enjoy the gorgeous views. There are 14 rapids along the 9.5-mile trip, but most of them are Class I and Class II; you shouldn't have a difficult time navigating them, and the kids will love the dash of excitement!
Want to feel like you've left the United States? Just about two and a half hours from Chicago, you'll find Holland. Holland, Michigan, that is. This Dutch town boasts beautiful European architecture. Performers in traditional clogs will delight you with their dancing. Enjoy delectable food and beautiful sights. Go to the town's Big Red Lighthouse to watch the sunset.
It takes about three hours to drive to Madison, Wisconsin from Chicago, and the time in the car is more than worth it. This exciting college town offers great cheese and amazing beer, but there is even more to love. There are plentiful opportunities for lakefront recreation, too. Rent bicycles to get around the city just like the locals.
Springfield, Illinois is another destination you should put on your list of day trips from Chicago. It takes about three hours to get to Springfield, but you should allow more time for your journey because you'll have to stop at some of the Route 66 roadside attractions along the way. The Paul Bunyan Hotdog Statue is a can't-miss photo op! Once you reach Springfield, check out the local zoo and the Lincoln Tomb, which is where the 16th president of the country was laid to rest.
Well over two and a half million people call Chicago home, and the dense population leads to heavy traffic conditions. Try to avoid major byways between four and five in the afternoon, which is when congestion tends to be the worst. Traffic is particularly bad in the summer, which is construction season. Make sure you have some great music playing in the car to get you through the wait.
When is the best time to visit Chicago? Every season has its charms. Holiday shopping along the Magnificent Mile is some of the best you'll find anywhere, but the weather can be cold and snowy during winter. Summer is humid and hot, but there are plenty of places where you can cool off, such as air-conditioned museums and water attractions. Fall and spring offer the mildest weather.
Where should you stay in the city? There are several neighborhoods to choose from. Hotels on the Loop are a bit pricy, but the area offers a convenient location that makes it easy to access all of the city's best attractions, such as Grant Park and the Willis Tower. The Westside is another great option. It is more affordable than downtown, and there are tons of ethnic restaurants in the area that are sure to delight your taste buds. Uptown, just north of downtown, is a cultural and artsy haven with tons of opportunities to enjoy live entertainment. If you want to stay in a quieter neighborhood, consider the area around O'Hare International Airport. As the third-most populated city in the country, Chicago is a brilliant metropolis that offers fun for everyone in the family. Explore the heart of the city, and then hop in your rental car to take in the charms of the Great Chicago area. It will be a trip you'll never forget!
© 2024 Enterprise Holdings, Inc. All rights Reserved.