Winfield Vacations from ￥374,634

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The Latest Winfield Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was ￥493,372, price is now ￥374,634 per person
￥374,634
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,139 reviews)
Great Staff. Super friendly and knowledgeable. Will be staying again. The beds are super comfortable.

Reviewed on Jul 9, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥562,542, price is now ￥416,023 per person
￥416,023
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥647,891, price is now ￥485,509 per person
￥485,509
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
We had our room upgraded to a suite which was a nice surprise. It was a great stay!

Reviewed on Jul 8, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥512,352, price is now ￥383,981 per person
￥383,981
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
View was beautiful, accommodations were excellent.

Reviewed on Jul 8, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was ￥561,004, price is now ￥427,625 per person
￥427,625
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Good location.

Reviewed on Jul 3, 2026

Find the Best Winfield Vacation Packages

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
The price is ￥16,889 per night from Jul 22 to Jul 23
￥16,889
￥20,864 total
Jul 22 - Jul 23
includes taxes & fees
8.6/10 Excellent! (1,058 reviews)
"Convenience"

Reviewed on Jul 7, 2026

Ameristar Casino Hotel East Chicago
Red Roof Inn Chicago - Lansing

Red Roof Inn Chicago - Lansing

2 out of 5
2450 East 173rd Street Lansing IL
Fully refundableReserve now, pay when you stay
The price is ￥12,001 per night from Jul 14 to Jul 15
￥12,001
￥13,560 total
Jul 14 - Jul 15
includes taxes & fees
4.6/10 (1,009 reviews)
"I booked a smoking room and got a non smoking room then I had made.food for me.and my partner to save in good cost and couldn't even use the microwave because it was broken had no tables or chairs to sit at no coffee pot couldn't watch TV because you had to pay to watch the TV and the place had roaches ..."

Reviewed on Jul 6, 2026

Red Roof Inn Chicago - Lansing
Comfort Suites near I-80 and I-94

Comfort Suites near I-80 and I-94

2.5 out of 5
2235 West 173rd St Lansing IL
Fully refundable
The price is ￥17,094 per night from Jul 27 to Jul 28
￥17,094
￥19,313 total
Jul 27 - Jul 28
includes taxes & fees
6.6/10 (877 reviews)
"The hotel is outdated. The light didn't work when you walk into the room. TV was rather small for the room, however it would have been okay if the guide was working. Overall the price was rather high for the room."

Reviewed on Jul 8, 2026

Comfort Suites near I-80 and I-94
See all 523 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.

Frequently asked questions

How much does a Winfield vacation package cost?
Offering great value package deals from ￥374,634 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?
You're likely to find reduced prices and greater availability in January, February and March. Take a look at our cheap Winfield vacation packages and you could get some excellent off-season deals.
How many days is enough for Winfield?
With a well-planned itinerary, you can easily visit the top Winfield attractions in a few days. But if you want to discover hidden spots or go on day trips, 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.
How to plan a trip to Winfield?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Winfield.
  2. Set a budget: Factor in costs such as food, flights and transportation when calculating how much to set aside for your trip to Winfield. Then, pick a property that fits your budget, whether that's a wallet-friendly stay or a lavish retreat.
  3. Decide how long to go for: Now that you know more about Winfield, you can work out the right length of your break. Put together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Winfield vacation package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.