Winfield Vacation Packages
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Your Winfield Vacation
Our vacation packages to Winfield provide endless opportunities to discover new sights, sounds and experiences. And with all the planning worked out, you can breathe easy and enjoy your city getaway without a worry in the world. Love to explore your new surroundings? Deep River Water Park, Crown Point Sports Complex and Lake County Fairgrounds are some of the leading places to visit during your trip to Winfield. A couple of clicks is all it takes to craft a tailor-made Winfield vacation on Expedia.
Top Winfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North
Downtown Chicago
Price was CA $816, price is now CA $643 per person
CA $643
per person
Apr 24 - Apr 27
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Staff was great but next to fire station. Beware very noisy if staying city view
Reviewed on Feb 8, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,409, price is now CA $1,720 per person
CA $1,720
per person
Apr 2 - Apr 6
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
DoubleTree by Hilton Chicago - Alsip
Price was CA $1,188, price is now CA $880 per person
CA $880
per person
Apr 9 - Apr 15
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (MDW)
8.2/10 Very Good! (1,007 reviews)
Everything was perfect and the front desk was so nice
Reviewed on Feb 10, 2026
La Banque Hotel
Price was CA $1,461, price is now CA $1,088 per person
CA $1,088
per person
May 5 - May 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,603, price is now CA $1,229 per person
CA $1,229
per person
Apr 9 - Apr 15
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (1,034 reviews)
Connecting to Northwestern Hospital was the greatest thing ever
Reviewed on Feb 11, 2026
Winfield Hotel Deals
Motel 6 Hammond, IN - Chicago Area
3840 179th St Hammond IN
The price is CA $70 per night from Feb 17 to Feb 18
CA $70
CA $78 total
Feb 17 - Feb 18
includes taxes & fees
6.2/10 (1,004 reviews)
Cool
Reviewed on Feb 7, 2026
Comfort Inn Hobart-Merrillville I-65
1915 Mississippi St Hobart IN
Fully refundableReserve now, pay when you stay
The price is CA $80 per night from Feb 19 to Feb 20
CA $80
CA $90 total
Feb 19 - Feb 20
includes taxes & fees
6.8/10 (720 reviews)
Staff was friendly. Good location.
Reviewed on Feb 1, 2026
Days Inn and Suites by Wyndham Hammond, IN
4000 Calumet Avenue Hammond IN
Fully refundableReserve now, pay when you stay
The price is CA $100 per night from Feb 22 to Feb 23
CA $100
CA $112 total
Feb 22 - Feb 23
includes taxes & fees
7.2/10 Good! (177 reviews)
Room was great, the weather was to be desired and the power went out for a few hours. The three stars was there was no accommodation for the inconvenience and the parking was horrible
Reviewed on Feb 9, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
