Steward Vacation Packages
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Your Steward Vacation
Our vacation packages to Steward let you create your own adventure. Tailor your journey to your interests and style and make every moment count in this interesting city. There's loads to do and see during your trip to Steward, including Rochelle Railroad Park and Chicagoland Skydiving Center. Whoever you're escaping with and whether your budget is big or small, your dream Steward vacation is only clicks away with Expedia.
Top Steward Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,003, price is now CA $755 per person
CA $755
per person
Jun 22 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,968, price is now CA $1,453 per person
CA $1,453
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,122 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was CA $1,123, price is now CA $834 per person
CA $834
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (2,281 reviews)
Wonderful location, staff were very helpful and room was clean. Older hotel but well maintained. Pricey but worthwhile for convenience sake.
Reviewed on May 5, 2026
Steward Hotel Deals
Home2 Suites by Hilton Dekalb
575 S ANNIE GLIDDEN RD DeKalb IL
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from May 27 to May 28
CA $178
CA $202 total
May 27 - May 28
includes taxes & fees
9.2/10 Wonderful! (446 reviews)
Very clean and kind people.
Reviewed on May 6, 2026
Hampton Inn DeKalb, IL
663 S. Annie Glidden Road DeKalb IL
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from May 20 to May 21
CA $173
CA $197 total
May 20 - May 21
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
The room was great, pillows were a little too soft, but they give you plenty of them. The room above us was causing a ruckus with people running around and bouncing. Went down and front desk after we couldn’t get them on phone took care of it.
Reviewed on Apr 26, 2026
Country Inn & Suites by Radisson, Sycamore, IL
1450 South Peace Road Sycamore IL
Fully refundable
The price is CA $119 per night from May 13 to May 14
CA $119
CA $133 total
May 13 - May 14
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
The pool wasn't open and they are in the process of remodeling which no one informed us before we came. The rooms have very little in them. Staff didn't really care if you were there or not
Reviewed on May 4, 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.
