Winfield Vacations from $180

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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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $306, price is now $180 per person
$180
per person
Feb 12 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on Dec 8, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,178, price is now $538 per person
$538
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (1,075 reviews)
We love it there! The best

Reviewed on Nov 30, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $457, price is now $221 per person
$221
per person
Feb 12 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city

Reviewed on Nov 26, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $618, price is now $338 per person
$338
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience.

Reviewed on Dec 9, 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $740, price is now $448 per person
$448
per person
Feb 12 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.

Reviewed on Dec 3, 2025

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Discover the most popular places to visit in Winfield

Deep River Water Park

4/5(34 reviews)

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

5/5(2 reviews)

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

3/5(1 review)

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
$99 nightly
The price is $111 total per night from Jan 1 to Jan 2
$111 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
Excellent

Reviewed on Dec 7, 2025

Ameristar Casino Hotel East Chicago
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 Dec 21 to Dec 22
$99 total
Dec 21 - Dec 22
Total with taxes and fees
7/10 Good! (134 reviews)
The staff didn’t seem courteous. They were courteous excellent service on my day that I spent the night at the Days Inn in Hammond I was scheduled to stay the 29 I came in on the 28ththe 29th. I had a very good time.

Reviewed on Dec 6, 2025

Days Inn and Suites by Wyndham Hammond, IN
Motel 6 Hammond, IN - Chicago Area

Motel 6 Hammond, IN - Chicago Area

2 out of 5
3840 179th St Hammond IN
$50 nightly
The price is $56 total per night from Dec 14 to Dec 15
$56 total
Dec 14 - Dec 15
Total with taxes and fees
6.2/10 (1,003 reviews)
.

Reviewed on Nov 23, 2025

Motel 6 Hammond, IN - Chicago Area
See all 480 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.

Find the Best Winfield Vacation Packages

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 $180 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.