Steward Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Steward Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,915
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Traveled with my partner, it felt romantic and we loved the view and all the nearby attractions. We were given a $10 credit to the restaurant but didn’t use them because we were too busy exploring the entire pier. There is no pool however the oak beach is nearby. The property felt safe although it was accessible to everyone, you had to use your room key to access the elevators. The pier closed at 10p to public so we had private access to the beautiful nighttime views. Make sure you wear walking shoes!! The only things that bothered us were, Stains on the floor and bench in our room, shower head had weak water flow, other than that it was an amazing stay!!! Definitely will be back with my children.
Reviewed on Aug 8, 2026
Ready to book your vacation to Steward?
Steward Hotel Deals
Best Western Sycamore Inn
1935 Dekalb Ave Sycamore IL
Fully refundableReserve now, pay when you stay
CA $124
CA $138 total
Aug 9 - Aug 10
includes taxes & fees
8.4/10 Very good! (466 reviews)
"My room was extremely clean, and the amenities provided were great. I really enjoyed staying there. The only off-putting experience I had was upon checking in. I presented a print out of my Expedia confirmation pages to the staff behind the counter. He frowned at me and said he couldn't find my reservation. ..."
Reviewed on Aug 8, 2026
Super 8 by Wyndham Rochelle
601 E Highway 38 Rochelle IL
Fully refundableReserve now, pay when you stay
CA $97
CA $108 total
Aug 10 - Aug 11
includes taxes & fees
8.2/10 Very good! (1,003 reviews)
"Clean rooms. A/C worked great. Staff very nice. Shower curtain was installed incorrectly. Was afraid it would fall down. Didn’t eat breakfast"
Reviewed on Aug 8, 2026
Hampton Inn DeKalb, IL
663 S. Annie Glidden Road DeKalb IL
Fully refundableReserve now, pay when you stay
CA $151
CA $172 total
Aug 16 - Aug 17
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"I gave the review 5 stars because of Brienna. I booked through Expedia, and when I got to the hotel late at night, there was something wrong with the way Expedia booked the stay, and they hadn't paid the hotel yet. I tried calling Expedia to see what was wrong because they had already charged my ..."
Reviewed on Aug 8, 2026
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.
Frequently asked questions
How much does a Steward vacation package cost?
You'll find cheap prices from CA $1,063 on Expedia for your Steward break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Steward costs.
What are the cheapest months to go to Steward?
You can generally find lower rates and better availability in January, February and November. Browse our cheap Steward vacation packages and you could get some great off-season deals.
How many days is enough for Steward?
With a well-planned itinerary, you can easily tick off the main Steward attractions in a handful of days. But if you want to discover lesser-known spots or go on day tours, think about booking your Steward vacation for longer.
How to find the best Steward package deals?
Begin your search for a Steward package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Steward package deal right away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Steward getaway off to a flying start.
Is it cheaper to book a Steward vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and stays separately. Better still, you can customize your Steward getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Steward?
If you have your Steward travel dates finalized, book as early as you can to grab some unbeatable deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Steward?
- Choose when to go: Check your calendar and pack your bags. Your favourite season and the activities on offer will also help you decide when to vacation in Steward.
- Plan your budget wisely: Besides the price of your hotel, you should factor in other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that may arise during your trip to Steward.
- Decide how long to go for: Now that you're more familiar with Steward, you can figure out the perfect length of your break. Create a rough plan and give yourself enough time to cover everything you want to do.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Steward vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
