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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,900, price is now CA $1,360 per person
CA $1,360
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
I booked this stay specifically because I saw they had a steam room and Sauna. They were both very pleasant and available 24/7. The room was very high quality with great views but if the city. The game rooms looked really nice and spacious but I sadly didn’t have time to enjoy that aspect of the hotel. There is also a great cafe and bakery connected to the lobby. I’m excited to book here again with a little more time to make the most of my stay

Reviewed on Apr 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $3,272, price is now CA $2,122 per person
CA $2,122
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great location! Easy parking and the rooms were gorgeous! We will definitely stay here next time we visit Chicago

Reviewed on Apr 10, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,647, price is now CA $1,868 per person
CA $1,868
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
We love staying at the Sable. Easy in and out parking. The Valet staff is wonderful. We enjoyed our breakfast. The room and view is always amazing.

Reviewed on Apr 11, 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $2,134, price is now CA $1,509 per person
CA $1,509
per person
Jun 19 - Jun 23
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work!

Reviewed on Apr 3, 2026

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $2,415, price is now CA $1,715 per person
CA $1,715
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.2/10 Wonderful! (371 reviews)
Breakfast was good. Room was clean with great air-conditioned. Staff very nice and happy. Customer service great. Had a great experience. Will be back and would recommend to everyone.

Reviewed on Apr 11, 2026

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Winfield Hotel Deals

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 $345 per night from May 9 to May 10
CA $345
CA $405 total
May 9 - May 10
includes taxes & fees
8.4/10 Very Good! (2,271 reviews)
It was nice

Reviewed on Apr 12, 2026

Hilton Chicago O'Hare Airport
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 $216 per night from Apr 23 to Apr 24
CA $216
CA $246 total
Apr 23 - Apr 24
includes taxes & fees
8.8/10 Excellent! (2,488 reviews)
Stayed here several times now and it is consistent. Clean and comfortable room. Friendly staff. Love the easy access to the convention center!

Reviewed on Apr 11, 2026

Hyatt Regency O'Hare Chicago
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 $275 per night from May 9 to May 10
CA $275
CA $323 total
May 9 - May 10
includes taxes & fees
8.6/10 Excellent! (1,237 reviews)
amenities were great and the Staff was welcoming.

Reviewed on Apr 9, 2026

Marriott Chicago O'Hare
See all 1,379 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

Wrigley Field

4.5/5(159 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(3 reviews)

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.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(460 reviews)

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

Navy Pier

What to do in Winfield

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Winfield

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