Countryside Vacations from $493
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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.
Level Chicago Fulton Market
Downtown Chicago
$976
per person
Nov 28 - Dec 4
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
We enjoyed our stay. The apartment was spotless, and the kitchen was well-stocked with appliances and utensils. We loved the Nespresso machine! Our only disappointment was the nighttime noise from nearby trains, plus one night of loud partying below our rental. The staff was friendly and helpful. We recommend this property.
Reviewed on Sep 26, 2026
Level Chicago – Old Town
Downtown Chicago
$621
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
Amazing stay for a family of four. The kids loved the pool, and the adults loved the hot tub! It felt close to the action, without being too close. Quiet but walkable to Navy Pier, Michigan Avenue, etc. Nearby multiple grocery stores. The building was well maintained and the neighborhood felt safe. The views from the room were unbelievable (the pictures don't do them justice). I would definitely stay here again.
Reviewed on Sep 26, 2026
The Emily Hotel
Downtown Chicago
$503
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Front desk staff was great as was housekeeping staff. Rooms were nothing special. Shower and bathroom floor had moldy grout. Bed was absolutely awful. Felt like sleeping on golfballs. Bar staff was awful. Wanted a quick drink while waiting for an Uber. Told them to charge to room. Bartender went MIA so we asked, what we assumed was a manager to ring us, he said ‘yep’ then went on to make some drinks, ignoring us. For the $$$ you can find much better hotels.
Reviewed on Sep 27, 2026
Don't see what you're looking for?
See all available trips from Columbus to Countryside
View all tripsWhat to do in Countryside
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Countryside Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$186 nightly
$221 total
Oct 25 - Oct 26
Total with taxes and fees
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$157 nightly
$187 total
Oct 26 - Oct 27
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$179 nightly
$213 total
Oct 14 - Oct 15
Total with taxes and fees
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.
Find the Best Countryside Vacation Packages
Countryside Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 6,000 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Brookfield Zoo, Galloping Ghost and Lizzadro Museum of Lapidary Art |
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Frequently asked questions
How much does a Countryside vacation package cost?
Offering great value package deals from $493 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?
- Pick your dates: What you want to do in Countryside and your favorite season will help you decide when to get away.
- 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.
- 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.
- 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.
- Combine your airfare and accommodations: Once you've nailed down your dates and duration, book the right Countryside vacation package for you.
- 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.
