Winfield Vacations from ￥234,060

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The Latest Winfield Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
Beautiful property, will definitely stay there again.

Reviewed on Jul 19, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Just a great property- really a 5 star experience-great location

Reviewed on Jul 20, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun 13, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Accommodations were great. Clean rooms and very convenient location. Service at the bar upstairs was pretty terrible the night we were there. Very unengaged and getting a drink took over 30 minutes

Reviewed on Jul 20, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
This hotel was fantastic. Staff was nice, breakfast well worth it, close to everything!

Reviewed on Jul 20, 2025

Find the Best Winfield Vacation Packages

Winfield Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is ￥21,377 per night from Aug 7 to Aug 8
￥21,377
￥24,366 total
Aug 7 - Aug 8
includes taxes & fees
8.6/10 Excellent! (1,758 reviews)
"It was a great hotel, clean, great ambience, open space. Clean rooms"

Reviewed on Jul 19, 2025

Hyatt Regency O'Hare Chicago
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd, Rosemont, IL
The price is ￥18,899 per night from Aug 10 to Aug 11
￥18,899
￥21,541 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (2,296 reviews)
"My husband and I stayed in mid-June for the 1st Annual Midwest Convention (held onsite), and while the event was great, the hotel’s accessibility and amenities were seriously lacking. There was insufficient parking for wheelchair users, which created immediate challenges. My husband is in a wheelchair, ..."

Reviewed on Jul 13, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥26,674 per night from Aug 9 to Aug 10
￥26,674
￥31,312 total
Aug 9 - Aug 10
includes taxes & fees
8/10 Very Good! (2,064 reviews)
"Hotel is just ok but we were delayed all day on a flight got in at 1:00am and obviously missed our connection. So we had about 5 hours before catching a new flight the next morning and you can literally walk to and from the hotel to the departure area in 5 mins. Staff was very friendly and ..."

Reviewed on Jul 17, 2025

Hilton Chicago O'Hare Airport
See all 1,294 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.

Discover the most popular places to visit in Winfield

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Winfield

River tour boat in Chicago

Architecture River Tour

￥7,149
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,597
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,597
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Winfield

Frequently asked questions

How much does a Winfield vacation package cost?
You'll find cheap prices from ￥234,060 on Expedia for your Winfield getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Winfield costs.
What are the cheapest months to go to Winfield?
Travel in the off-season and you're likely to find cheap Winfield vacation packages. Bear in mind that public holidays and local events and festivals can impact prices, so do a little research before booking.
How many days is enough for Winfield?
The ideal length for your Winfield vacation depends on what you'd like to see. Usually, a few days to a week will give you time to hit all the main attractions and explore some hidden treasures along the way.
How to find the best Winfield package deals?
Start your search for a Winfield package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Winfield package deal straight away, just play around with your dates and search again. Remember 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 break by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winfield?
Score amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Winfield break.
How to plan a trip to Winfield?

  1. Choose the right 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 like flights, transportation and food when working out how much to set aside for your trip to Winfield. Then, select a property that suits your budget, whether that's an economical stay or a high-end retreat.
  3. Determine how many days away: Start by making a list of all the attractions you'd like to experience in Winfield. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Winfield vacation package that brings all your bookings together.

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