Countryside Trips (flight + hotel)

Photo by Monica Ferro

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Top hotels in Countryside

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
7.8/10 Good! (8,950 reviews)
"The room and bathroom were both spacious with high ceilings. Great view on the lake side."

Reviewed on Aug 3, 2025

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Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P10,086 per night from Aug 21 to Aug 22
P10,086
P13,294 total
Aug 21 - Aug 22
includes taxes & fees
8.2/10 Very Good! (1,824 reviews)
"could not use my Plat Amex, to upgrade bc of expedia."

Reviewed on Aug 3, 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is P8,492 per night from Aug 24 to Aug 25
P8,492
P9,969 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,330 reviews)
"Nice location"

Reviewed on Aug 1, 2025

Crowne Plaza Chicago West Loop by IHG
See all 5,039 properties in Countryside
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.

Popular places to visit

McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park showing modern architecture, autumn leaves and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Six Flags Great America which includes rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Countryside

River tour boat in Chicago

Architecture River Tour

P2,350
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

P2,296
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

P2,551
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Countryside

Frequently asked questions

How much does a Countryside vacation package cost?
Offering great value package deals 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?
If you're hoping to score a cheap Countryside vacation package, consider visiting in January, February and April. You'll generally find lower rates on hotels and flights during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Countryside?
Usually, a handful of days is enough to check out the top attractions during your Countryside vacation. But if you'd like to have time to rest or go on day trips, consider 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. Choose your dates: What you plan to do in Countryside and your preferred season can help you decide when to go.
  2. Work out your budget: Ensure you have enough money to pay for everything from dining out and transportation to activities and airfares. Your accommodations will probably be the largest expense during your trip to Countryside.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Countryside. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Countryside vacation package that brings all your bookings together.

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