Winfield Vacation Packages

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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!

Top Winfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
per person
Jul. 2 - Jul. 6
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
This was a really nice hotel in a great area with tons of restaurants, well lit up streets and easy walking in the downtown River North area. The hotel itself was lively on the ground floor with its bar and restaurant and the room was clean and well laid out and quiet overall The bed/pillows were really, really comfortable. I would stay here again anytime.

Reviewed on May 18, 2024

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 15 - Aug. 20
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
7.8/10 Good! (1,743 reviews)
Just overall a really nice place

Reviewed on May 22, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 8 - Jul. 11
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 8 - Jul. 11
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (687 reviews)
Beautiful property, lovely staff, very well-located for a weekend trip to Chicago where we needed to be near the Loop.

Reviewed on May 23, 2024

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 2 - Jul. 6
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
EXCEPTIONAL SERVICE!!

Reviewed on May 21, 2024

Winfield Hotel Deals

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
The price is CA $232 per night from Jun. 14 to Jun. 15
CA $232
CA $272 total
includes taxes & fees
Jun 14 - Jun 15
8.2/10 Very Good! (1,002 reviews)
"The staff were so helpful and friendly, makes me want to come back. Great customer service."

Reviewed on May 13, 2024

Marriott Chicago O'Hare
Best Western At O'Hare
Best Western At O'Hare
2.5 out of 5
10300 W Higgins Road, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from May 27 to May 28
CA $127
CA $145 total
includes taxes & fees
May 27 - May 28
7.2/10 Good! (1,842 reviews)
"Clean and staff very friendly."

Reviewed on May 23, 2024

Best Western At O'Hare
SureStay Plus Hotel by Best Western Chicago Lombard
SureStay Plus Hotel by Best Western Chicago Lombard
2.5 out of 5
222 E 22nd Street, Lombard, IL
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from May 26 to May 27
CA $124
CA $137 total
includes taxes & fees
May 26 - May 27
8.6/10 Excellent! (1,536 reviews)
Will stay again
"Had a very short 1-night stay. Was worth it. Room was clean, hotel was clean, and the people were curteous. It was quiet so we got the rest we needed."

Reviewed on May 24, 2024

SureStay Plus Hotel by Best Western Chicago Lombard
See all 1,289 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winfield vacation package cost?
Starting from a low CA $674, a package is your gateway to inexpensive travel. Create your own Winfield getaway by choosing from our great range of hotels, airfares and rental cars.
How do I get a cheap travel package to Winfield?
One word: bundle. Flights, rental cars and hotels — combine whatever you need into a Winfield vacation package and save. Score even better deals when you add extras such as experiences or tours to your booking. But that’s not the only good part. You have the flexibility to customize your vacation your way. We offer more than 550 airlines and 1,000,000 hotels in all corners of the globe, so that everyone has an opportunity to travel and fulfill those vacation fantasies.
Where should I stay in Winfield?
With popular attractions like Central Dupage Hospital and Cantigny Park in this area, see if you can find a hotel near either of them. Cantigny Golf Club is another sight in Winfield that people flock to.
How far in advance should I book my Winfield vacation?
To score discount prices, book early. Air carriers typically begin selling tickets, along with some of the lowest fares, up to 12 months ahead of time. Hotels, car rental and experiences should also be booked early so you can have the pick of the bunch. If you’ve decided on a last-minute getaway to Winfield, there are always lots of great deals to be had on Expedia. Check them out now!
What does an Expedia Winfield travel package include?
Hotels, car rentals and flights — we bring you the very best deals. All you’ll have to do is select your preferred combination. Once you’ve made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to put together an unforgettable Winfield getaway.
What should I know before booking a Winfield travel package?
When you book your hotels, flights and car rentals together, you’ll nab awesome discounts. Whether you’re organizing a beach escape in a villa or prefer to stay in a cozy apartment in the city, Expedia will help make it happen.
Can I choose my airline with a Winfield Expedia vacation package?
With a vacation package, you’re the boss. Whether you want to fly to Winfield in economy or business class, simply select from the available airline options. Expedia has access to over 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Winfield vacation package?
Plans can change without warning, so yes. You may be able to cancel or alter your Winfield vacation package for free within 24 hours of booking. For older bookings, you can still make the necessary changes, but your car rental company, hotel or airline may impose a fee. Want more information? Visit our Customer Service Portal. We’re here to help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Winfield

Image for Wrigley Field

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

4.5/5(5 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for McCormick Place

McCormick Place

4.5/5(141 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in Winfield

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

CA $311
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
See all activities in Winfield
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.