Chicago is a major city, so there’s no shortage of hotels to choose from. However, for a more personalized experience and to get more for your money, consider vacation rental homes in Chicago. Choose from small studio apartments to spacious townhouses all throughout the city. If you’ve never stayed in a vacation rental or this is your first trip to Chicago, check out these tips for choosing the best one.

Compare Amenities of Vacation Rentals

Suzanne Tucker/Shutterstock

One of the best things about choosing a vacation rental is that you have a whole slew of amenities to choose from. Unlike in a hotel where you have to pay for amenities you might not necessarily use, browsing rental home listings allows you to select only the properties that have what you need and skip over the ones that don’t. If you plan to cook while on vacation, opt for vacation rentals in Chicago that have a full kitchen.

Choose a Vacation Rental Close to Your Activities

Rudy Balasko/Shutterstock

Select vacation home rentals in Chicago that are close to the attractions and places you plan to frequent. Chicago is a large city, and you don’t want to spend most of your time and money traveling within the city. While the price tag on a vacation rental home in Des Plaines near the airport might sound convenient, you could spend 45 minutes to an hour just getting into the city.

Consider Your Travel Budget

Mark Baldwin/Shutterstock

On the flip side, if you’re working with a tight budget, a vacation rental home in one of Chicago’s suburbs might offer the budget flexibility that you need. Some of the most expensive real estate is in The Loop — a neighborhood in the business district with a convenient location. Find a balance between the space and amenities you need and the price you want to spend.

Check Out Transportation and Parking Options


Like any major city, Chicago has a strong public transportation system. The L is the elevated rapid transit system that goes all through the city and makes stops in some of Chicago’s suburbs. Additionally, there are bus stops throughout the city to take you to all of the major attractions with ease. If you’re driving to Chicago, check what the parking options are for your vacation rental home. Parking is scarce in many parts of the city, and often comes at a premium. Homes with a place to park your car are a bonus.

Find the Right Chicago Neighborhood

Maria Sbytova/Shutterstock

If you see a rental home that catches your eye, take some time to learn about the neighborhood before booking. Vacation rentals in downtown Chicago are close to the action; however, this part of town has a lot of tourists and noise, too. Rentals in Lincoln Park and the Northside are a bit farther off the beaten path, allowing you to experience Chicago like a local. The Gold Coast is filled with historic homes and is largely residential for a quieter stay.