Chicago Vacations from $425

You'll find cheap prices from $425 on Expedia for your Chicago escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Chicago costs.

You can generally find lower prices and greater availability in December, January and February. Explore our cheap Chicago vacation packages and you could score some excellent off-season deals.

To fully enjoy a Chicago vacation, we suggest staying for 2 days. Divide your time between visiting Shedd Aquarium, Chicago Theatre and other leading sights, on top of exploring neighborhoods like Central Chicago and Magnificent Mile. If you've got some time to spare, include a day trip or tour in your Chicago vacation itinerary.

Chicago has everything you need for an awesome break — culture, views and dining are just the start. Whether you want to visit sights such as Millennium Park and Art Institute of Chicago, or venture off the beaten track, you'll find plenty to explore on your Chicago vacation.

Use Expedia's filters to find some great Chicago package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Chicago package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.

Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still have the freedom to create a customized Chicago vacation by choosing your favorite accommodation type, airline and car class.

Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Chicago break.

1. Choose your dates: What you'd like to do in Chicago and your favorite season can help you decide when to go.
2. Set your budget: Consider costs like flights, food and transportation when calculating how much to put aside for your trip to Chicago. Then, pick a property that works with your budget, whether that's a wallet-friendly stay or a high-end retreat.
3. Organize your Chicago escape with our trip planning tool: Look for and book accommodations and things to do all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Chicago together.
4. Decide how long to go for: Now that you're up to speed on Chicago, you can work out the ideal length of your vacation. Pull together a draft itinerary and give yourself enough time to cover everything you want to do.
5. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Chicago vacation package.
6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some awesome things to do in Chicago. Book tickets or make reservations in advance to save time and avoid the hassle of trying to find activities once you arrive.

Jet off on your dream getaway to Chicago with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait for the next payday — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snag great deals before they disappear.