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.
Pendry Chicago
Downtown Chicago
CA $1,444
per person
Dec 13 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,156 reviews)
This is an excellent hotel. Very central and easily walkable to most attractions. The staff were superb and very helpful. The only downside (which wasn't a huge bother for me, but worth mentioning nevertheless) is that occasionally the rooms can be quite noisy from the revving of engines (motorcycles and cars) on the busy North Michigan Avenue. Notwithstanding this, I would not hesitate to stay here again.
Reviewed on Oct 5, 2026
Ready to book your vacation to Winfield?
Winfield Hotel Deals
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
CA $83
CA $92 total
Nov 5 - Nov 6
includes taxes & fees
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
CA $230
CA $270 total
Oct 30 - Oct 31
includes taxes & fees
8.6/10 Excellent! (1,421 reviews)
"No breakfast was included. Parking was $38 just to be in a parking lot. With what the cost of the room being $209 a night breakfast should have been included and no cost for parking. I know I will never stay at this hotel ever again and would inform anyone I know not to stay there either. Also the ..."
Reviewed on Oct 5, 2026
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
CA $205
CA $234 total
Nov 1 - Nov 2
includes taxes & fees
8.8/10 Excellent! (2,870 reviews)
"The overall stay was good. However waiting in line for breakfast once it's busy needs work. It should be organized better with guests paying and ppl whom did pay. It was a hot mess on Friday morning that just pasted."
Reviewed on Oct 6, 2026
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.
Stay near popular Winfield attractions
Royal Golf Club at Klein Creek
Enjoy a round of golf in Winfield at Royal Golf Club at Klein Creek. Stroll along the lakeside or attend a hockey game in this family-friendly area.
What to do in Winfield
Skydeck Chicago at Willis Tower
CA $59
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Winfield vacation package cost?
You'll find cheap prices from CA $864 on Expedia for your Winfield getaway. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Winfield costs.
What are the cheapest months to go to Winfield?
The off-season is the best time to head to Winfield if you're trying to save. Another tip for scoring cheap Winfield vacation packages? Avoid visiting during public holidays and any major events.
How many days is enough for Winfield?
Typically, a handful of days is enough to go to the top attractions during your Winfield vacation. However, if you'd like to have some time to rest or take day tours, think about extending your itinerary.
How to find the best Winfield package deals?
Use Expedia's filter tool to help you find some tempting Winfield package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Winfield package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Winfield vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging stays and flights separately. Better still, you can tailor your Winfield escape to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Winfield?
Secure fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Winfield break.
How to plan a trip to Winfield?
- Choose when to travel: Check your diary and pack your bags. Your preferred season and the type of activities on offer will also help you decide when to vacation in Winfield.
- Set a budget: Consider costs such as flights, transportation and food when working out how much to set aside for your trip to Winfield. Then, select a property that fits your budget, whether that's an economical stay or a more upscale getaway.
- Decide how many days away: Start by listing all the sights and activities you want to experience in Winfield. Then, estimate how long you'll need at each, as well as any travel time.
- Combine your flights and hotel: Awesome destination, check. Length of stay, check. 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.
