Steward Vacations from $438

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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.

The Latest Steward vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$438
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Great location, great services and clean

Reviewed on Sep 10, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$902
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
The pool & jacuzzi was perfect, this hotel is beautiful

Reviewed on Sep 7, 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
$1,007
per person
Nov 28 - Dec 4
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Location and facility was very nice

Reviewed on Sep 7, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$680
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
Save 100% on your flight
$1,249
per person
Nov 28 - Dec 4
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
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Steward Hotel Deals

Best Western Sycamore Inn

Best Western Sycamore Inn

1935 Dekalb Ave Sycamore IL
Fully refundableReserve now, pay when you stay
$95 nightly
$106 total
Sep 20 - Sep 21
Total with taxes and fees
Best Western Sycamore Inn
Best Western Rochelle Inn & Suites near DeKalb

Best Western Rochelle Inn & Suites near DeKalb

1133 N. 7th St., Hwy 251 and Rt, 38 Rochelle IL
Fully refundableReserve now, pay when you stay
$110 nightly
$122 total
Sep 15 - Sep 16
Total with taxes and fees
Best Western Rochelle Inn & Suites near DeKalb
Motel 6 Sycamore, IL

Motel 6 Sycamore, IL

1860 Dekalb Ave Sycamore IL
Fully refundableReserve now, pay when you stay
$71 nightly
$79 total
Sep 13 - Sep 14
Total with taxes and fees
7.8/10 Good! (681 reviews)
"Clean rooms, very nice staff"

Reviewed on Sep 7, 2026

Motel 6 Sycamore, IL
See all 33 properties in Steward
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.

Find the Best Steward Vacation Packages

Steward Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rockford, IL (RFD-Greater Rockford)
Population
260
Top Sights
Shabbona Lake State Park, Chicagoland Skydiving Center and Rochelle Railroad Park

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Frequently asked questions

How much does a Steward vacation package cost?
You can pick up a vacation package to this top destination from $438 on Expedia. However, how much your vacation to Steward costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Steward?
If you're looking to book a cheap Steward vacation package, consider visiting in November, December and January. You'll usually find lower prices on flights and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for Steward?
With a well-planned itinerary, you can easily visit the main Steward sights in a handful of days. But if you'd like to venture off the beaten track or go on day tours, think about booking your Steward vacation for longer.
How to find the best Steward package deals?
Use Expedia's filter tool to find some fabulous Steward package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Steward package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Steward vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still get the flexibility to create a customized Steward vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Steward?
If you have your Steward vacation dates confirmed, book as soon as you can to score some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Steward vacation packages?
Secure your dream escape to Steward with our Book Now, Pay Later vacations. There's no need to save up or wait until the next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stick to your budget and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.