Winfield Vacations from $214

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Your Winfield Vacation

Our vacation packages to Winfield provide endless opportunities to discover new sights, sounds and experiences. And with all the planning worked out, you can breathe easy and enjoy your city getaway without a worry in the world. Love to explore your new surroundings? Deep River Water Park, Crown Point Sports Complex and Lake County Fairgrounds are some of the leading places to visit during your trip to Winfield. A couple of clicks is all it takes to craft a tailor-made Winfield vacation on Expedia.

The Latest Winfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $405, price is now $214 per person
$214
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine

Reviewed on Oct 4, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,020, price is now $524 per person
$524
per person
Dec 31 - Jan 3
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $470, price is now $244 per person
$244
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Healthy breakfast and very clean hotel with friendly staff.

Reviewed on Oct 10, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $918, price is now $510 per person
$510
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on Oct 11, 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $391, price is now $220 per person
$220
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on Oct 9, 2025

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Discover the most popular places to visit in Winfield

Deep River Water Park

Have a fun-filled day with the family at Deep River Water Park as part of your trip to Crown Point. Stroll along the lakeside or attend a sporting event in the area.

Deep River Water Park

Crown Point Sports Complex

Explore the great outdoors at Crown Point Sports Complex, a lovely green space in Crown Point. Amble around the area's lakeside or visit its shops.

Crown Point Sports Complex

Lake County Fairgrounds

Enjoy an outing to Lake County Fairgrounds during your stay in Crown Point. Amble around the area's lakeside or visit its shops.

Lake County Fairgrounds

Winfield Hotel Deals

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd., East Chicago, IN
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $143 total per night from Oct 14 to Oct 15
$143 total
Oct 14 - Oct 15
Total with taxes and fees
8.4/10 Very Good! (1,013 reviews)
"It was very nice!!"

Reviewed on Oct 6, 2025

Ameristar Casino Hotel East Chicago
Fairfield Inn and Suites By Marriott Merrillville

Fairfield Inn and Suites By Marriott Merrillville

2.5 out of 5
8275 Georgia St, Merrillville, IN
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Oct 19 to Oct 20
$104 total
Oct 19 - Oct 20
Total with taxes and fees
7.8/10 Good! (1,002 reviews)
"Breakfast was wonderful with the staff there very polite and helpful!"

Reviewed on Oct 6, 2025

Fairfield Inn and Suites By Marriott Merrillville
Days Inn and Suites by Wyndham Hammond, IN

Days Inn and Suites by Wyndham Hammond, IN

2 out of 5
4000 Calumet Avenue, Hammond, IN
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $99 total per night from Nov 3 to Nov 4
$99 total
Nov 3 - Nov 4
Total with taxes and fees
7/10 Good! (107 reviews)
"Staff super friendly and clean rooms"

Reviewed on Oct 7, 2025

Days Inn and Suites by Wyndham Hammond, IN
See all 476 properties in Winfield
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.

Winfield Essential Information

Language
English
Currency
U.S dollars
Population
5,400
Top Sights
Deep River Water Park, Big Bass Beach and Crown Point Sports Complex

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Frequently asked questions

How much does a Winfield vacation package cost?
Offering great value package deals from $214 on Expedia, you'll be thrilled with how little a vacation to Winfield costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Winfield?
January, October and December are great times to look for cheap Winfield vacation packages. Opting to travel in quieter periods means you'll typically find reduced prices on hotels and flights.
How many days is enough for Winfield?
With a well-organized schedule, you can easily visit the most popular Winfield sights in a handful of days. But if you prefer to discover hidden gems or go on day tours, think about booking your Winfield vacation for longer.
How to find the best Winfield package deals?
Begin your search for a Winfield package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Winfield package deal right away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winfield adventure underway.
Is it cheaper to book a Winfield vacation as a package?
You can enjoy significant savings on your next Winfield retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winfield?
If you're planning a spontaneous Winfield getaway, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Winfield vacation packages?
Your Winfield break should be an escape from your daily routine, not a reason for money-related stress. So to allow you a little more flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.