Winfield Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

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.
Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,014 reviews)
Convenient to O’Hare, but the free shuttle did not answer our phone call when we were at the airport needing a ride. From the hotel it was very easy to book it via the front desk.

Reviewed on Jul. 6, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,333 reviews)
Hotel staff and room were awesome..bed very comfortable. Coffee shop was great had great fast breakfast options. Had Miss Rickie's one day was really great food. Only complaint would be the rooftop bar evening clientele...did not feel comfortable and they were loud and raucous.

Reviewed on Jul. 8, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Beautiful!! Location, room, security, everything was perfect! Very classy, elegant!

Reviewed on Jul. 9, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
It’s a great location for walk around the beautiful downtown of Chicago. People were so helpful and friendly. Definitely I’ll consider coming back.

Reviewed on Jul. 7, 2025

Ready to book your vacation to Winfield?

 

Choose your dates

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 $196 per night from Aug 6 to Aug 7
CA $196
CA $224 total
Aug 6 - Aug 7
includes taxes & fees
8.6/10 Excellent! (1,710 reviews)
"Great facility! Clean and wonderful staff"

Reviewed on Jul. 6, 2025

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
The price is CA $184 per night from Aug 10 to Aug 11
CA $184
CA $210 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (2,280 reviews)
Chicago Trip
"Nice hotel close to our venue. Was able to enjoy breakfast and dinner at the hotel. Would be nice if the pool was in a more secluded patio area"

Reviewed on Jul. 6, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
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 $220 per night from Jul 26 to Jul 27
CA $220
CA $258 total
Jul 26 - Jul 27
includes taxes & fees
8.4/10 Very Good! (1,075 reviews)
"I like the service"

Reviewed on Jul. 6, 2025

Marriott Chicago O'Hare
See all 1,288 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

Discover the most popular places to visit in Winfield

Wrigley Field featuring central business district, a city and a sporting event

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
Navy Pier

Navy Pier

4.5/5(459 reviews)

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

Navy Pier
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

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

What to do in Winfield

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $61
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Winfield

Frequently asked questions

How much does a Winfield vacation package cost?
You'll find cheap prices from CA $488 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.