Title: Winfield Vacation Packages & Trips 2026 from CA $1,057 | Expedia.ca

[Hotels in Winfield](https://expedia.ca/Winfield-Hotels.d6215979.Travel-Guide-Hotels)[Vacation Rentals in Winfield](https://expedia.ca/Winfield-Vacation-Rentals.d6215979.Travel-Guide-VacationRentals)[Winfield Car Rentals](https://expedia.ca/Car-Rentals-In-Winfield.d6215979.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6215979/82584498-74af-4810-bd48-bb2705a610d9.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Winfield Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

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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](https://www.expedia.ca/Wheaton-College-Chicago.d6091385.Vacation-Attraction), [College of Dupage](https://www.expedia.ca/College-Of-Dupage-Chicago.d6135577.Vacation-Attraction) and [North Central College Fine & Performing Arts](https://www.expedia.ca/North-Central-College-Fine-Performing-Arts-Chicago.d553248621532658522.Vacation-Attraction), 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.

![Harbor Shores on Lake Geneva](https://images.trvl-media.com/lodging/1000000/10000/4700/4614/3a08fccc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Harbor Shores on Lake Geneva

CA $1,057

per person

Jun 3 - Jun 9

found 3 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,318 reviews)

During off season not as many activities

Reviewed on Mar 16, 2026

![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago Fulton Market

Downtown Chicago

CA $1,451

per person

May 7 - May 11

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (421 reviews)

10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.

Reviewed on Mar 23, 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,451

per person

Jun 4 - Jun 8

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (3,495 reviews)

Clean room. Very friendly staff

Reviewed on Mar 25, 2026

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,510

per person

Jun 4 - Jun 8

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (2,401 reviews)

Rooms are nice, great view, valet parking is great

Reviewed on Mar 24, 2026

![Lodge Geneva National](https://images.trvl-media.com/lodging/1000000/900000/893400/893361/c30b4670_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Lodge Geneva National

CA $1,404

per person

Jun 3 - Jun 9

found 3 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,366 reviews)

It was ok rooms were noisy can here everything in hall and in next room

Reviewed on Mar 23, 2026

## Ready to book your vacation to Winfield?

Choose your dates

## Winfield Hotel Deals

![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/a48bf16b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

CA $315

CA $370 total

Apr 25 - Apr 26

includes taxes & fees

8.4/10 Very Good! (2,238 reviews)

Yyy

Reviewed on Mar 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=25%2F04%2F2026&endDate=26%2F04%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true&regionId=6215979)

![Hyatt Regency O'Hare Chicago](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/2c5e0afa_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

Fully refundableReserve now, pay when you stay

CA $185

CA $211 total

Apr 6 - Apr 7

includes taxes & fees

8.8/10 Excellent! (2,431 reviews)

Architecturally beautiful hotel. Our room was very clean, updated, crisp linens, good bed and pillows. We paid for the breakfast buffet and it was well worth it. I really enjoyed my stay at this Hyatt. It will be my go to whenever I need to stay near O'hare.

Reviewed on Mar 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&selected=5403&PinnedHotelID=5403&HadPinnedHotel=true&regionId=6215979)

![Marriott Chicago O'Hare](https://images.trvl-media.com/lodging/1000000/10000/300/281/c9c2af9c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Marriott Chicago O'Hare

8535 West Higgins Road Chicago IL

Fully refundableReserve now, pay when you stay

CA $205

CA $241 total

Apr 3 - Apr 4

includes taxes & fees

8.6/10 Excellent! (1,237 reviews)

It was all good!

Reviewed on Mar 23, 2026

[](https://expedia.ca/Hotel-Search?startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&selected=281&PinnedHotelID=281&HadPinnedHotel=true&regionId=6215979)

[See all 1,373 properties in Winfield](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026&regionId=6215979)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Winfield

![Wrigley Field featuring central business district, a city and a sporting event](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wrigley Field

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

[](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction)

![Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept](https://images.trvl-media.com/place/6156167/9a44be22-322b-4187-8844-e2aa99b46184.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Michigan Avenue

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. 

[](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction)

![Chicago Skyline at North Beach](https://images.trvl-media.com/place/6069213/e3e08680-ba57-4e08-8e19-fef490757e5e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area. 

[](https://expedia.ca/Naval-Base-Great-Lakes-Chicago.d6069213.Vacation-Attraction)

### What to do in Winfield

![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 360 CHICAGO Observation Deck

CA $37

per adult

**86%** of travellers recommend

[](https://expedia.ca/things-to-do/360-chicago-observation-deck.a170348.activity-details)

![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wendella's 90-min Chicago River Architecture Tour

CA $55

per adult

**94%** of travellers recommend

[](https://expedia.ca/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details)

![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Flyover in Chicago

CA $52

per adult

**98%** of travellers recommend

[](https://expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details)

[See all activities in Winfield](https://expedia.ca/things-to-do/search?rid=6215979)

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