Chicago Cheap Vacations

Playing around with the easy-to-use search wizard is one of the best ways to find affordable Chicago vacation packages on Expedia. Tap your dates in and it'll offer some of the cheapest Chicago getaways within seconds. You can also use the maximum price filter to view deals within your budget. If you're traveling during peak season dates, it's a good idea to book early to snag some of the best offers. You may score irresistible last-minute specials for travel in low season.

On Expedia's last-minute travel deals page, you'll encounter a plethora of special offers for late vacations to Chicago. Remember, you're more likely to bag savings on last-minute travel during off-peak periods. Consider checking different departure dates, too. Expedia's nifty search tool lets you compare some of the best last-minute Chicago vacation packages. The handy filters let you tailor your trip according to your preferences, including hotel star rating, amenities, and property location.

For some of the cheapest vacation packages to Chicago from $221, it's best to travel during low season dates. With fewer people traveling during these periods, flights and hotels usually have lower prices. It's also a good idea to avoid popular travel times. These include spring break, Thanksgiving, and other federal holidays. On Expedia, you'll encounter some of the best travel deals to Chicago. Best of all, vacation payment plans mean you can spread the cost of your trip over 3, 6, or 12 months.

Yes, many of Expedia's cheap Chicago getaway packages allow for free cancellation in case your plans change. Follow the easy steps to cancel by logging into your Expedia account and clicking on “Trips” page'. Keep in mind, though, that each vacation package has different cancellation policies, so be sure to look over them before booking. The good news is you'll clearly see this information on Expedia when you book. There's even a free cancellation search filter that lets you view flexible vacations to Chicago.

A multitude of exclusive travel deals you won't find anywhere else is one of the top reasons to book your cheap Chicago vacation package with Expedia. And with one of the widest choices of flights and hotels available, you'll easily find the right trip for you. The handy search wizard and filters let you compare hundreds of great deals in seconds, too. It's not only the cheap prices either: Expedia's booking protection and 24/7 support give you peace of mind before and during your 2025 trip.

When searching for budget vacations to Chicago, look out for the green savings label. This indicates you've snagged a deal only available on Expedia. Another popular way of getting money off your 2025Chicago vacation is by joining One Key. Expedia's amazing reward program gives you access to hundreds of member-only discounts on select hotels. Keep a look out for the blue savings label in the search results. Best of all, One Key is free to join.

You'll often snag package savings on your Chicago vacation when bundling together your flights and accommodation. Expedia even shows you how much you're saving by booking a package. It's not just cheaper prices, either. Packages often have more flexible booking conditions, meaning you're more likely to get a refund in case your 2025 plans change. While booking flights and hotels separately usually requires full payment, Chicago vacation packages often let you pay a small upfront deposit to confirm.

Settling on your dates is usually the first step to planning an affordable Chicago getaway. If you're traveling during peak season dates, it's a good idea to book your trip in advance. This way, you're more likely to bag early-bird deals. Don't rule out a last-minute travel deal for low season dates, though. Once you've picked your dates, tap them into the search wizard to see some of the best Chicago vacation package deals. Hop over to Expedia's vacation planning page for more tips for your dream vacation.