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.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Price was CA $1,069, price is now CA $777 per person
CA $777
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,007 reviews)
Nice setup, courteous staff, wasn’t expecting to have to pay $100 deposit on top of the money I paid Expedia, also an additional fee of $17 that Expedia did not cover even though they summed up all the charges before our stay. Seems to be a consistent issue with Expedia.

Reviewed on Jul 15, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,113, price is now CA $1,436 per person
CA $1,436
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.

Reviewed on Jul 14, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,578, price is now CA $1,110 per person
CA $1,110
per person
Sep 24 - Sep 27
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was CA $1,458, price is now CA $1,029 per person
CA $1,029
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (657 reviews)

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $2,224, price is now CA $1,635 per person
CA $1,635
per person
Oct 10 - Oct 14
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Queen is very small but nice staff

Reviewed on Jul 16, 2026

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
Fully refundableReserve now, pay when you stay
The price is CA $237 per night from Aug 3 to Aug 4
CA $237
CA $270 total
Aug 3 - Aug 4
includes taxes & fees
Hyatt Regency O'Hare Chicago
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
The price is CA $392 per night from Aug 7 to Aug 8
CA $392
CA $460 total
Aug 7 - Aug 8
includes taxes & fees
8.4/10 Very good! (2,362 reviews)
"Mediocre room, less mediocre food."

Reviewed on Jul 15, 2026

Hilton Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road Schiller Park IL
Fully refundable
The price is CA $161 per night from Aug 10 to Aug 11
CA $161
CA $185 total
Aug 10 - Aug 11
includes taxes & fees
Comfort Suites Chicago O'Hare Airport
See all 1,341 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.
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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 $777 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.