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.
JW Marriott Chicago
Downtown Chicago
Price was CA $1,039, price is now CA $707 per person
CA $707
per person
May 1 - May 3
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Bottle of waters were not stocked in the refrigerator.
Reviewed on Jan 6, 2026
La Banque Hotel
Price was CA $1,044, price is now CA $743 per person
CA $743
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,155, price is now CA $828 per person
CA $828
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Montreal Metropolitan Airport (YHU) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything was amazing, specially the breakfast buffet.
Reviewed on Feb 7, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $949, price is now CA $708 per person
CA $708
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Montreal Metropolitan Airport (YHU) to Chicago (ORD)
9/10 Wonderful! (766 reviews)
Great stay. Would come again.
Reviewed on Jan 19, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,362, price is now CA $1,032 per person
CA $1,032
per person
May 5 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!
Reviewed on Feb 2, 2026
Steward Hotel Deals
Hampton Inn DeKalb, IL
663 S. Annie Glidden Road DeKalb IL
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Feb 15 to Feb 16
CA $133
CA $151 total
Feb 15 - Feb 16
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
The whole facility was great room was clean and roomy. The breakfast was great the biscuits and gravy tasted homemade.
Reviewed on Feb 3, 2026
Country Inn & Suites by Radisson, Sycamore, IL
1450 South Peace Road Sycamore IL
The price is CA $114 per night from Feb 17 to Feb 18
CA $114
CA $127 total
Feb 17 - Feb 18
includes taxes & fees
8.4/10 Very Good! (968 reviews)
Clean rooms and courteous staff. I requested for Kate check out and also asked if I can use the lobby for few more hours and both my requests were met. Very happy with my stay
Reviewed on Jan 28, 2026
Best Western Sycamore Inn
1935 Dekalb Ave Sycamore IL
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Feb 15 to Feb 16
CA $127
CA $141 total
Feb 15 - Feb 16
includes taxes & fees
8/10 Very Good! (388 reviews)
Clean room. Good breakfast.
Reviewed on Jan 23, 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.
