Steward Vacations from $433

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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.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $820, price is now $433 per person
$433
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (237 reviews)
This hotel was probably the cleanest hotel I’ve seen and their staff was very kind!

Reviewed on Sep 1, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,288, price is now $720 per person
$720
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
Beautiful property close to the Fulton Market and night life. The room was eccentric in a way that made our stay cool. It was clean and stocked with a bar & snacks for additional purchase. We enjoyed the Rooftop Cinema on the 6th floor, it was playing my favorite movie! And the restaurant Fora had a delicious breakfast. We definitely recommend this property.

Reviewed on Sep 6, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $856, price is now $492 per person
$492
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,373 reviews)
This hotel was so nice. It is literally steps from Michigan Avenue and so convenient to walk anywhere. The hotel itself is modern, clean, and well taken care of. The only negative thing I can say is we went to the rooftop bar at 10:30 and they told us it was closed. It’s supposed to close at 11 and there were other people sitting outside still having drinks. That was disappointing but all of the other amenities this hotel offers is great. You get a free breakfast too that’s pretty decent. For the cost and location, this was excellent.

Reviewed on Sep 5, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,975, price is now $1,170 per person
$1,170
per person
Nov 24 - Nov 29
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!

Reviewed on Aug 31, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was $2,375, price is now $1,514 per person
$1,514
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug 12, 2025

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Steward Hotel Deals

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
$93 nightly
The price is $103 total per night from Sep 8 to Sep 9
$103 total
Sep 8 - Sep 9
Total with taxes and fees
Country Inn & Suites by Radisson, Sycamore, IL
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
$122 nightly
The price is $138 total per night from Sep 28 to Sep 29
$138 total
Sep 28 - Sep 29
Total with taxes and fees
Hampton Inn DeKalb, IL
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
$68 nightly
The price is $75 total per night from Sep 14 to Sep 15
$75 total
Sep 14 - Sep 15
Total with taxes and fees
Super 8 by Wyndham Rochelle
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.

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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 $433 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.