
Sycamore Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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Your Sycamore Vacation
Our vacation packages to Sycamore offer endless opportunities to uncover new sights, sounds and tastes. And with all the planning worked out, you can relax and enjoy your city adventure without a worry in the world. Like to venture out and explore? Northern Illinois University, Huskie Stadium and Ellwood House Museum are among the top-rated places to visit during your trip to Sycamore. Your ultimate Sycamore vacation is just clicks away. Search hotels, flights and more on Expedia for an adventure that's tailored to suit your travel style.
Top Sycamore Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,135, price is now CA $745 per person
CA $745
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (282 reviews)
The staff were excellent
Reviewed on Aug. 21, 2025

Park Hyatt Chicago
Downtown Chicago
Price was CA $2,170, price is now CA $1,307 per person
CA $1,307
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug. 10, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,793, price is now CA $1,090 per person
CA $1,090
per person
Oct 19 - Oct 22
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.
Reviewed on Aug. 25, 2025

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,699, price is now CA $1,070 per person
CA $1,070
per person
Oct 6 - Oct 10
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
We loved the experience! We shall come back again😊
Reviewed on Aug. 24, 2025

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,291, price is now CA $845 per person
CA $845
per person
Oct 19 - Oct 22
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on Aug. 21, 2025
Sycamore Hotel Deals

Country Inn & Suites by Radisson, Sycamore, IL
1450 South Peace Road, Sycamore, IL
Fully refundable
The price is CA $128 per night from Aug 31 to Sep 1
CA $128
CA $142 total
Aug 31 - Sep 1
includes taxes & fees

Best Western Sycamore Inn
1935 Dekalb Ave, Sycamore, IL
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Aug 31 to Sep 1
CA $137
CA $152 total
Aug 31 - Sep 1
includes taxes & fees

Motel 6 Sycamore, IL
1860 Dekalb Ave, Sycamore, IL
Fully refundableReserve now, pay when you stay
The price is CA $95 per night from Aug 26 to Aug 27
CA $95
CA $106 total
Aug 26 - Aug 27
includes taxes & fees
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.
Frequently asked questions
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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.