Winfield Vacations from $371

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Your Winfield Vacation

When you organize a vacation package to Winfield, you can relax and enjoy your escape knowing your travel plans have been worked out ahead of time. Uncover the many charms of this amazing city from your base in a neighborhood like Medinah, which is great for golfing. Fill your itinerary with tours of Wheaton College, College of Dupage and North Central College Fine & Performing Arts, some of the attractions you just have to see during a trip to Winfield. Expedia has what you need to escape your daily routine. Tailor your vacation to Winfield to suit your travel style, whatever that may be!

The Latest Winfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $658, price is now $371 per person
$371
per person
Jul 6 - Jul 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
It’s all good but they didn’t allow me to take just a cup of coffee to my room and that I did not like at all. After seeing the tiktok where girls washes underwear in hotel room coffee machine I will never make coffee in hotels rooms ever and that’s why I wanted to enjoy the morning coffee from dining hall but wasn’t allowed therefore my rating is F

Reviewed on Apr 15, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $1,282, price is now $703 per person
$703
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Yessss it’s was amazing

Reviewed on Apr 13, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,613, price is now $917 per person
$917
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
This property never disappoints! The staff are awesome, particularly Nu at the front desk! Always very pleasant and friendly, provides awesome service every time we visit!

Reviewed on Apr 13, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $673, price is now $390 per person
$390
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Nice hotel I would stay here again

Reviewed on Apr 15, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $933, price is now $546 per person
$546
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Helpful staff, great location, adequate rooms!

Reviewed on Apr 14, 2026

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Discover the most popular places to visit in Winfield

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(4,925 reviews)

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

Navy Pier

What to do in Winfield

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

$40
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Winfield

Winfield Hotel Deals

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
$204 nightly
The price is $240 total per night from May 9 to May 10
$240 total
May 9 - May 10
Total with taxes and fees
8.4/10 Very Good! (2,277 reviews)
I would rate this hotel as good to excellent if not for one employee. I stayed two nights and all the staff including front desk, restaurant and housekeeping were customer friendly and efficient with one exception. I returned back to the main entrance of the hotel on the second night after a long ...

Reviewed on Apr 12, 2026

Hilton Chicago O'Hare Airport
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
$122 nightly
The price is $140 total per night from Apr 22 to Apr 23
$140 total
Apr 22 - Apr 23
Total with taxes and fees
8.8/10 Excellent! (2,498 reviews)
The staff was not helpful. We stayed there the night before an international flight and the night we got back. We had to pay $50 per day for parking.

Reviewed on Apr 14, 2026

Hyatt Regency O'Hare Chicago
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $221 total per night from Apr 30 to May 1
$221 total
Apr 30 - May 1
Total with taxes and fees
8.6/10 Excellent! (1,236 reviews)
amenities were great and the Staff was welcoming.

Reviewed on Apr 9, 2026

Marriott Chicago O'Hare
See all 1,379 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
Closest Airport
O'Hare Intl. Airport (ORD)
Population
9,700
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
DuPage Childrens Museum, Lynfred Winery and Pirates Cove Childrens Theme Park

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Frequently asked questions

How much does a Winfield vacation package cost?
You'll find cheap prices from $371 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?
If you're looking to book a cheap Winfield vacation package, consider planning a trip in December, January and February. You'll usually find better prices on hotels and airfares during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Winfield?
Usually, a handful of days is enough to explore the main attractions during your Winfield vacation. But if you'd like to have some time to rest or take day trips, think about extending your itinerary.
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.
Does Expedia offer Book Now, Pay Later Winfield vacation packages?
Set off on your dream getaway to Winfield with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or hold off until payday — we've teamed up with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.