Winfield Vacations from $391

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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 Garden Inn Naperville/Warrenville

Hilton Garden Inn Naperville/Warrenville

3 out of 5
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,007 reviews)
quiet, stily , good price

Reviewed on Jul 30, 2025

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,006 reviews)
The staff was very friendly and was great for walking distance to everything!

Reviewed on Aug 3, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
i’ve stayed here a few times and love it. it’s my go to, i highly recommend this place!

Reviewed on Aug 11, 2025

citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (3,522 reviews)
Met my expectations and it was convenient. The only issue is the app was buggy so it was hard to schedule a cleaning.

Reviewed on Aug 12, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Terrace 16 resto has the best view in Chicago outstanding service. Hotel is located right next to the river cruises. Walgreens is 3 minutes away by foot. Very safe neighborhood several excellent restaurants within 10 minutes on foot. Try Wildberry resta for breakfast excellent food. Sanda for Asian food and Grand Boucher French The pizza place next to hotel (bonjiourno) overrated and subpar

Reviewed on Aug 12, 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
$99 nightly
The price is $111 total per night from Aug 20 to Aug 21
$111 total
Aug 20 - Aug 21
Total includes taxes and fees
8.4/10 Very Good! (1,011 reviews)
"Air Conditioner"

Reviewed on Aug 11, 2025

Ameristar Casino Hotel East Chicago
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
$113 nightly
The price is $127 total per night from Sep 2 to Sep 3
$127 total
Sep 2 - Sep 3
Total includes taxes and fees
8.8/10 Excellent! (1,006 reviews)
"This place is absolutely haunted. Everything feels dated and kind of grimy without being actually dirty, if that makes any sense. My husband complained about a weird smell on the third floor, but thankfully we were on the second. I'm pretty sure that there are only two people working in the hotel ..."

Reviewed on Aug 12, 2025

Spring House Inn
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $114 total per night from Sep 1 to Sep 2
$114 total
Sep 1 - Sep 2
Total includes taxes and fees
8.4/10 Very Good! (1,005 reviews)
Very nice place to stay
"Good breakfast and the bed was very comfortable"

Reviewed on Aug 10, 2025

Best Western Indian Oak
See all 457 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.

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Frequently asked questions

How much does a Winfield vacation package cost?
Offering great value package deals from $391 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.