Winfield Vacations from $279

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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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $431, price is now $279 per person
$279
per person
Dec 3 - Dec 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
Staff was great and the room was clean!

Reviewed on Oct 29, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,440, price is now $428 per person
$428
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
My experience at the Sheraton was terrible. I was assigned a room right next to the elevator, where there was also a shared microwave for guests on the floor. A large group of young people was placed in the same hallway. They appeared to be intoxicated and made excessive noise from around 11 p.m. until nearly 4 a.m., making it impossible to sleep. I called the front desk three times asking for help, but the noise continued and nothing was resolved. I felt very unsafe and completely let down by the hotel staff. Guests should be able to expect a restful stay and a response when they ask for help. I left exhausted and deeply disappointed. I expected much better from the Sheraton.

Reviewed on Oct 28, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $503, price is now $292 per person
$292
per person
Dec 3 - Dec 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Great staff they accommodating us.

Reviewed on Oct 30, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $648, price is now $377 per person
$377
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Super clean. Super views. Super amenities. Will stay again.

Reviewed on Oct 26, 2026

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was $1,110, price is now $685 per person
$685
per person
Dec 16 - Dec 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (1,005 reviews)

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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
$133 nightly
The price is $149 total per night from Nov 30 to Dec 1
$149 total
Nov 30 - Dec 1
Total with taxes and fees
Ameristar Casino Hotel East Chicago
Motel 6 Hammond, IN - Chicago Area

Motel 6 Hammond, IN - Chicago Area

2 out of 5
3840 179th St Hammond IN
$60 nightly
The price is $67 total per night from Nov 1 to Nov 2
$67 total
Nov 1 - Nov 2
Total with taxes and fees
6.6/10 (1,003 reviews)
"Perfect stay for the price, need better pillows."

Reviewed on Oct 29, 2026

Motel 6 Hammond, IN - Chicago Area
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $116 total per night from Nov 1 to Nov 2
$116 total
Nov 1 - Nov 2
Total with taxes and fees
Spring House Inn
See all 507 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 $279 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.