Steward Vacations from $514

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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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was $898, price is now $514 per person
$514
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,131 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.

Reviewed on Apr 24, 2026

Voyageur Inn and Conference Center

Voyageur Inn and Conference Center

2 out of 5
Price was $1,272, price is now $713 per person
$713
per person
Jul 13 - Jul 17
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
8.2/10 Very Good! (512 reviews)
Very clean room, had everything we needed

Reviewed on Mar 1, 2026

Super 8 by Wyndham Reedsburg

Super 8 by Wyndham Reedsburg

2 out of 5
Price was $1,172, price is now $663 per person
$663
per person
Jul 13 - Jul 17
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
7/10 Good! (612 reviews)
The hallways smell like cigarette smoke. There was a truck running under our window and you could smell it.

Reviewed on Apr 19, 2026

Holiday Inn Express & Suites Reedsburg - Dells Area by IHG

Holiday Inn Express & Suites Reedsburg - Dells Area by IHG

2.5 out of 5
Price was $1,331, price is now $780 per person
$780
per person
Jul 13 - Jul 17
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
9.6/10 Exceptional! (160 reviews)
Brand new, very clean, and well maintained.

Reviewed on Apr 24, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was $1,759, price is now $1,043 per person
$1,043
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,458 reviews)
We were there for a wedding and didn't have time for much else.

Reviewed on Apr 26, 2026

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Steward Hotel Deals

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
$130 nightly
The price is $148 total per night from May 18 to May 19
$148 total
May 18 - May 19
Total with taxes and fees
9.2/10 Wonderful! (443 reviews)
Very nice place ! Entire hotel was spotless, nice size rooms with comfortable beds and pillows. Front desk people were great! Very friendly.

Reviewed on Apr 25, 2026

Home2 Suites by Hilton Dekalb
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
$124 nightly
The price is $141 total per night from May 11 to May 12
$141 total
May 11 - May 12
Total with taxes and fees
9.4/10 Exceptional! (1,001 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

Hampton Inn DeKalb, IL
Comfort Inn & Suites Rochelle - DeKalb

Comfort Inn & Suites Rochelle - DeKalb

2.5 out of 5
1133 N 7th St Rochelle IL
Fully refundable
$76 nightly
The price is $84 total per night from May 19 to May 20
$84 total
May 19 - May 20
Total with taxes and fees
8/10 Very Good! (490 reviews)
The staff is always very ki

Reviewed on Apr 17, 2026

Comfort Inn & Suites Rochelle - DeKalb
See all 35 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 $514 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.