Steward Vacations from $297

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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.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $448, price is now $297 per person
$297
per person
May 14 - May 18
found 24 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
8/10 Very Good! (478 reviews)
Was an wonderful experience. The staff was very kind and helpful. The view was amazing. Highly recommend any time of the year!

Reviewed on Jan 12, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,151, price is now $615 per person
$615
per person
May 3 - May 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean amenities, amazing food, and great service!

Reviewed on Feb 27, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $881, price is now $541 per person
$541
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The room was great and clean , there was a toilet issue but the staff members gladly were readily available to fix it all ! The amenities including the hot tub, and pool as well as the in room service breakfast was 5/5 . Would absolutely stay here again .

Reviewed on Feb 17, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $625, price is now $388 per person
$388
per person
May 25 - May 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $677, price is now $430 per person
$430
per person
May 3 - May 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
Clean room, I’m always glad to stay here

Reviewed on Feb 27, 2026

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Steward Hotel Deals

Hampton Inn DeKalb, IL

Hampton Inn DeKalb, IL

3 out of 5
663 S. Annie Glidden Road DeKalb IL
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $129 total per night from Mar 16 to Mar 17
$129 total
Mar 16 - Mar 17
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
Room was great, very clean, breakfast was free and amazing,, Staff Customer Service was off the chain, everyone very friendly and accommodating.

Reviewed on Feb 24, 2026

Hampton Inn DeKalb, IL
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
$85 nightly
The price is $94 total per night from Mar 8 to Mar 9
$94 total
Mar 8 - Mar 9
Total with taxes and fees
8.6/10 Excellent! (980 reviews)
I would not recommend this hotel to anyone. Did not have a good experience. The bad: - Checkout time on Expedia is 12:00, but at the hotel its posted as 11:00. On top of this, housekeeping staff was knocking on my door at 9:45. - So called "fitness center" has crapy old equipment from 1960's, light ...

Reviewed on Feb 26, 2026

Country Inn & Suites by Radisson, Sycamore, IL
Home2 Suites by Hilton Dekalb

Home2 Suites by Hilton Dekalb

3 out of 5
575 S ANNIE GLIDDEN RD DeKalb IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $154 total per night from Mar 18 to Mar 19
$154 total
Mar 18 - Mar 19
Total with taxes and fees
9.2/10 Wonderful! (420 reviews)
Great hotel!

Reviewed on Feb 25, 2026

Home2 Suites by Hilton Dekalb
See all 37 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 $297 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.