Steward Vacations from $608

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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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $985, price is now $608 per person
$608
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (501 reviews)
Good

Reviewed on Jul 20, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,541, price is now $878 per person
$878
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,649, price is now $942 per person
$942
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (523 reviews)

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,326, price is now $849 per person
$849
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,037 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,065, price is now $702 per person
$702
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,603 reviews)

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Steward Hotel Deals

Super 8 by Wyndham Rochelle

Super 8 by Wyndham Rochelle

2 out of 5
601 E Highway 38 Rochelle IL
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $70 total per night from Aug 2 to Aug 3
$70 total
Aug 2 - Aug 3
Total with taxes and fees
Super 8 by Wyndham Rochelle
Country Inn & Suites by Radisson, Sycamore, IL

Country Inn & Suites by Radisson, Sycamore, IL

2.5 out of 5
1450 South Peace Road Sycamore IL
Fully refundable
$88 nightly
The price is $97 total per night from Aug 11 to Aug 12
$97 total
Aug 11 - Aug 12
Total with taxes and fees
8.4/10 Very Good! (1,006 reviews)
"Easy check in/out, helpful & accommodating staff. Clean, comfortable rooms w/friendly & helpful house keeping. Good, standard breakfast and decent gym equipment!"

Reviewed on Jul 20, 2026

Country Inn & Suites by Radisson, Sycamore, IL
Best Western Sycamore Inn

Best Western Sycamore Inn

2.5 out of 5
1935 Dekalb Ave Sycamore IL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Aug 2 to Aug 3
$90 total
Aug 2 - Aug 3
Total with taxes and fees
Best Western Sycamore Inn
See all 32 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 $608 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.