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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $1,268, price is now CA $823 per person
CA $823
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (2,509 reviews)
The room was clean, bed was good and the only "issue" was the size of the bathroom. For long stays might be something that I would not like but the stay was only 3 nights so I would say it was perfect. Gym could use some update as well, but same logic, for shorter stays the property is amazing. Great location, near everything.

Reviewed on Apr 28, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,439, price is now CA $910 per person
CA $910
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.

Reviewed on Apr 24, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,360, price is now CA $884 per person
CA $884
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.

Reviewed on Apr 27, 2026

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was CA $1,250, price is now CA $828 per person
CA $828
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,569 reviews)
The Royal Sonesta was a complete delight! They had staff available to help at all times, and they were always cheerful and friendly. I’ll definitely be back!

Reviewed on Apr 29, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,467, price is now CA $1,649 per person
CA $1,649
per person
Jul 13 - Jul 17
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,853 reviews)
Absolutely fantastic will be back

Reviewed on Apr 27, 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 $338 per night from May 2 to May 3
CA $338
CA $397 total
May 2 - May 3
includes taxes & fees
8.4/10 Very Good! (2,283 reviews)
After two international flights this was a welcome overnight and we loved the view of the airport and downtown from our room. The restaurant was decent for a quick bite, and when our coffee machine didn’t work, they kindly gave us a voucher to buy one at their cafe. Comfortable overall stay with ...

Reviewed on Apr 29, 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 $196 per night from May 10 to May 11
CA $196
CA $223 total
May 10 - May 11
includes taxes & fees
8.8/10 Excellent! (2,513 reviews)
Breakfast buffet was only option

Reviewed on Apr 29, 2026

Hyatt Regency O'Hare Chicago
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from May 10 to May 11
CA $114
CA $126 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (2,706 reviews)
The entire hotel smelled amazing, clean but also a nice scent. Also it's been nicely updated, lobby and room. The breakfast was great. Hot or cold, good variety.

Reviewed on Apr 29, 2026

SureStay Plus Hotel by Best Western Chicago Lombard
See all 1,377 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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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
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
94% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.