Countryside Holidays

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Top hotels in Countryside

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 S$145 per night from 20 Apr to 21 Apr
S$145
includes taxes & fees
20 Apr - 21 Apr
8.6/10 Excellent! (1,024 reviews)
"Its really a good hotel and at a good.location and easy to commute"

Reviewed on 29 Mar,2025

Crowne Plaza Chicago West Loop by IHG
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$285 per night from 4 Apr to 5 Apr
S$285
includes taxes & fees
4 Apr - 5 Apr
8.8/10 Excellent! (2,018 reviews)
"Great service. In the heart of Downtown Chicago. Would definitely stay again."

Reviewed on 31 Mar,2025

Swissotel - Chicago
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$213 per night from 20 Apr to 21 Apr
S$213
includes taxes & fees
20 Apr - 21 Apr
8.2/10 Very Good! (3,804 reviews)
"I did my daughter’s birthday here and it was amazing! We all enjoyed our stay and was very pleased with the breakfast"

Reviewed on 29 Mar,2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,474 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.

Frequently asked questions

How much does a Countryside holiday package cost?
Offering great value package deals on Expedia, you’ll be thrilled with how little a holiday 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 holiday package, consider visiting in January, February and April. You’ll generally find lower rates on hotels and flights during these quieter months — ideal for travellers 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 holiday. 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 holiday as a package?
An Expedia holiday package could land you great savings when compared to booking stays and flights separately. Better still, you can customise 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 holiday 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 accommodation 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 holiday package that brings all your bookings together.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

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
Soldier Field showing a city, modern architecture and a skyscraper

Soldier Field

4/5(44 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field

What to do in Countryside

Flyover in Chicago

Flyover in Chicago

S$51
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

S$65
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

S$59
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Countryside

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.