A vast wheat field under a cloudy sky.

Countryside Vacations from $321

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Countryside Vacation

Book a Countryside vacation package and get set for a wonderful adventure. Known for its rural countryside and spectacular views, there's plenty to keep you on the move in this fascinating city. If your trip to Countryside includes a little sightseeing, take in famous attractions like Brookfield Zoo, SeatGeek Stadium and Chicago Ridge Shopping Mall. Browse Expedia's wide range of travel options and start planning your dream vacation to Countryside now.

The Latest Countryside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 15 - Dec 18

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.4/10 - Exceptional (194 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $454
    $321
    per traveler
    found 1 day ago
    The Talbott, Autograph Collection
  • Dec 20 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,875 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $1,483
    $471
    per traveler
    found 2 days ago
    Sheraton Grand Chicago Riverwalk
  • Dec 24 - Dec 29

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (602 reviews)
    "If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $856
    $557
    per traveler
    found 1 day ago
    Level Chicago Fulton Market
  • Jan 22 - Jan 25

    Level Chicago – Old Town + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.2/10 - Wonderful (558 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $733
    $498
    per traveler
    found 1 day ago
    Level Chicago – Old Town
  • Dec 15 - Dec 18

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (5,646 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $474
    $336
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago

Where to stay in Countryside

Explore the charming atmosphere of Countryside, IL, where family-friendly adventures and outdoor activities await. Discover the enchanting vibes of the glorious countryside, nearby wine country, and the delightful charm reminiscent of the French countryside for a memorable vacation experience.

Chicago

For travelers seeking a vibrant urban experience, Chicago offers an array of attractions that will delight both families and weekend getaway enthusiasts. With its iconic Michigan Avenue for shopping, the lively Navy Pier for entertainment, and the expansive McCormick Place for events, there's never a shortage of activities. Nestled within Chicago, Countryside provides easy access to these highlights, making it an ideal base for your stay. Booking a hotel in Chicago ensures you’re at the heart of a bustling metropolis filled with opportunities for exploration.

Indian Head Park

Experience the charm of Indian Head Park, an excellent hub for travelers seeking a blend of outdoor adventure and urban excitement. This welcoming city offers easy access to popular attractions like the Donald E. Stephens Convention Center, Morton Arboretum, and the College of DuPage, making it ideal for family getaways or business trips. Located about 0.8 miles from Countryside, Indian Head Park provides a smart choice for your stay, balancing convenience with an inviting atmosphere.

Hodgkins

If you are a traveler looking for a blend of business and leisure, look no further than Hodgkins, a charming city that offers a variety of experiences. Explore the nearby Drury Lane Theater for captivating performances, enjoy the serene beauty of Morton Arboretum, or indulge in shopping at local centers and malls. Hodgkins, located about 1 mile from Countryside, ensures easy access to these attractions, making it a smart choice for your stay.

Burr Ridge

Burr Ridge stands out as a prime spot for travelers interested in both city and outdoor experiences. With its vibrant shopping center and arena entertainment facility, visitors can enjoy a mix of leisure and excitement. The nearby Morton Arboretum offers a beautiful natural retreat for those looking to unwind. Located about 2 miles from Countryside, Burr Ridge makes for an excellent base to explore the area, ensuring a delightful stay for families, couples, and business travelers alike.

Willow Springs

Travelers visiting the area often choose Willow Springs, especially families and nature enthusiasts seeking close proximity to vibrant outdoor spaces and cultural experiences. With attractions like the historic University of Chicago, the Moraine Valley Community College Fine and Performing Arts Center, and the lively Drury Lane Theater, Willow Springs offers a delightful blend of city charm and nature. Located about 2 miles from Countryside, it’s an ideal base for exploring the region, making Willow Springs a smart choice for your stay.

What to do in Countryside

Countryside Hotel Deals

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

How much does a Countryside vacation package cost?

Offering great value package deals from $321 on Expedia, you'll be thrilled with how little a vacation to Countryside costs! Expedia's packages mean less travel planning for you and greater savings.

What are the cheapest months to go to Countryside?

February, August and September are the best times to look for cheap Countryside vacation packages. Choosing to travel in less busy periods means you can usually find lower prices on flights and accommodations.

How many days is enough for Countryside?

Typically, a handful of days is enough to check out the main attractions during your Countryside vacation. But if you'd like to have more time to kick back or go on day trips, think about extending your itinerary.

How to find the best Countryside package deals?

Finding a cheap Countryside package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Countryside package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.

Is it cheaper to book a Countryside vacation as a package?

An Expedia vacation package could land you great savings when compared to booking stays and flights separately. Better still, you can customize your Countryside escape to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.

When to book a vacation package to Countryside?

Land incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Countryside trip.

How to plan a trip to Countryside?

  1. Pick your dates: What you want to do in Countryside and your favorite season will help you decide when to get away.
  2. Plan your budget wisely: As well as the price of your hotel, you should factor in other expenses too. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Countryside.
  3. Explore Countryside with our trip planning tool: Gain insights into the top attractions and best stays for your trip to Countryside. You can also save your must-visit places, collaborate with your group and organize all your plans in one place.
  4. Decide how long to go for: Now that you're up to speed on Countryside, you can figure out the ideal length of your break. Create a draft itinerary and allocate enough time to cover everything you want to see.
  5. Combine your airfare and accommodations: Once you've nailed down your dates and duration, book the right Countryside vacation package for you.
  6. Book any day trips or activities: Now to the fun part — locking in everything you want to see and do. Browse some of the top things to do in Countryside and reserve your tickets in advance to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Countryside vacation packages?

If you're like us, you love going away but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Countryside vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.