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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,270, price is now CA $872 per person
CA $872
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,858 reviews)
Rooms were very bare. Ours didn’t even have a fridge, we had to ask for one. Then they gave us a beverage fridge. No dresser or storage anywhere. Bathroom had no counter space. Shower would get water everywhere because the curtain wasn’t long enough. Super tight space not worth the price.

Reviewed on Jul 30, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,699, price is now CA $1,088 per person
CA $1,088
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Fue solo una noche, pero todo fue 100/10.

Reviewed on Jul 30, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,396, price is now CA $925 per person
CA $925
per person
Sep 4 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (504 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $2,053, price is now CA $1,406 per person
CA $1,406
per person
Sep 4 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Z

Reviewed on Jul 29, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,435, price is now CA $994 per person
CA $994
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,038 reviews)

Ready to book your vacation to Winfield?

 

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Winfield Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is CA $237 per night from Aug 30 to Aug 31
CA $237
CA $270 total
Aug 30 - Aug 31
includes taxes & fees
Hyatt Regency O'Hare Chicago
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr Naperville IL
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Aug 6 to Aug 7
CA $121
CA $134 total
Aug 6 - Aug 7
includes taxes & fees
DoubleTree by Hilton Lisle Naperville
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 refundableReserve now, pay when you stay
The price is CA $169 per night from Aug 10 to Aug 11
CA $169
CA $192 total
Aug 10 - Aug 11
includes taxes & fees
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 1,387 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

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.
See properties

What to do in Winfield

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Winfield

Frequently asked questions

How much does a Winfield vacation package cost?
You'll find cheap prices from CA $872 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.