Winfield Vacations from $184

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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.
Crowne Plaza Chicago SW - Burr Ridge by IHG

Crowne Plaza Chicago SW - Burr Ridge by IHG

4 out of 5
Save 100% on your flight
Price was $283, price is now $184 per person
$184
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (1,004 reviews)
Amazing hotel, great service cleanly housekeeping would highly recommend I have it in my favorites. Plan to go again anytime I’m in Illinois. Wouldn’t choose another one.

Reviewed on Dec 31, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $489, price is now $284 per person
$284
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
Liked the neat and tidy room I was assigned to. They accommodated my request for the shower. Staff showed great hospitality special thanks to Sasha, Konnor, Rigel. Would have been greater had there been more amenities like body lotion, sleeper, toothbrush, etc.

Reviewed on Jan 7, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,009, price is now $611 per person
$611
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
This hotel was the perfect one. Right in the middle of everything and very convenient

Reviewed on Jan 17, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,163, price is now $723 per person
$723
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Yes didn’t know you get free breakfast

Reviewed on Jan 4, 2026

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Save 100% on your flight
Price was $419, price is now $268 per person
$268
per person
Mar 19 - Mar 22
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.6/10 Good! (1,002 reviews)
The gym hours need to be limited so guest don't hear people dropping weights during late night hours Windows are drafty, causing constant cycling of HVAC. Exhaust vent in bathroom was gross

Reviewed on Jan 12, 2026

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Discover the most popular places to visit in Winfield

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

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
Navy Pier featuring a sunset and rides

Navy Pier

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

Navy Pier

What to do in Winfield

Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$83
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Blackhawks Ice Hockey Game at United Center

Chicago Blackhawks Ice Hockey Game at United Center

$67
per adult
Chicago Blackhawks Ice Hockey Game at United Center
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
$196 nightly
The price is $230 total per night from Feb 7 to Feb 8
$230 total
Feb 7 - Feb 8
Total with taxes and fees
8.2/10 Very Good! (2,178 reviews)
Stayed prior to flight, clean, quiet room!

Reviewed on Jan 13, 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
$135 nightly
The price is $154 total per night from Jan 18 to Jan 19
$154 total
Jan 18 - Jan 19
Total with taxes and fees
8.8/10 Excellent! (2,311 reviews)
Fine if you need to be close to O'Hare.

Reviewed on Jan 15, 2026

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
Fully refundable
$105 nightly
The price is $120 total per night from Jan 21 to Jan 22
$120 total
Jan 21 - Jan 22
Total with taxes and fees
8.6/10 Excellent! (2,692 reviews)
Great hotel! Other than the unexpected $29/day uncovered parking far away and very thin blankets, I had a lovely time for a business trip with my coworkers!

Reviewed on Jan 11, 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 1,378 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 $184 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.