Steward Holidays

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    Save up to €900 when you book a flight and hotel together*

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Top Flight + Hotel Deals in Steward

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €5,523, price is now €4,697 per person
€4,697
per person
1 Oct - 7 Oct
found 17 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €6,131, price is now €5,273 per person
€5,273
per person
1 Oct - 7 Oct
found 17 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €5,626, price is now €4,842 per person
€4,842
per person
1 Oct - 7 Oct
found 17 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Excellent location. Staff very nice. Room big and bed very comfortable. But noisy. As is all of Chicago. Trying to sell in room soap products for exorbitant prices tachy as hell. Rooftop lounge had sadly very short hours and limited open days. Seems a shame to waste such an opportunity.

Reviewed on 14 Jul 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €5,500, price is now €4,878 per person
€4,878
per person
1 Oct - 7 Oct
found 17 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
The check in was seamless. Lobby spotless. Room was very clean and tidy. Rooftop area was super.

Reviewed on 12 Jul 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was €5,458, price is now €4,885 per person
€4,885
per person
1 Oct - 7 Oct
found 17 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,388 reviews)
Beautiful hotel with nice city views. Friendly staff. So many hidden fees, doubled the cost.

Reviewed on 12 Jul 2026

Top hotels in Steward

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
The price is €61 per night from 2 Aug to 3 Aug
€61
2 Aug - 3 Aug
includes taxes & 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
The price is €85 per night from 22 Jul to 23 Jul
€85
22 Jul - 23 Jul
includes taxes & fees
8.4/10 Very good! (1,007 reviews)
"The floor was stained and sticky. The handle on the sink in the bathroom came off when we tried to turn on the water, we called the front desk to let them know and they never came to fix it. Instead they turned off all the water to the room and did not answer when we tried to call and ask about it. ..."

Reviewed on 13 Jul 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
The price is €73 per night from 22 Jul to 23 Jul
€73
22 Jul - 23 Jul
includes taxes & fees
8.4/10 Very good! (442 reviews)
"The trim was peeling off around the floor. The floor going into the bathroom was separated about half inch. Toilet seat was loose. Long hair was in shower and on floor in bathroom. Sri at front desk when I checked out couldn't get my receipt to print so after 3-4 minutes I said never mind."

Reviewed on 13 Jul 2026

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.

Frequently asked questions

How much does a Steward holiday package cost?
You can pick up a holiday package to this top destination from €4,697 on Expedia. However, how much your holiday 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?
January, February and November are great times to look for cheap Steward holiday packages. Opting to travel in less busy months means you can usually find better prices on accommodation and flights.
How many days is enough for Steward?
The ideal duration for your Steward holiday depends on what you'd like to do and see. Generally, a few days to a week will give you enough time to hit all the main attractions and discover some hidden gems along the way.
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 holiday package well in advance.
Is it cheaper to book a Steward holiday as a package?
Expedia holiday 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 customised Steward holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Steward?
If you have your Steward holiday 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.
How to plan a trip to Steward?

  1. Choose your travel dates: The things you plan to do in Steward and your favourite season can help you decide when to get away.
  2. Set your budget: Consider expenses such as transportation, flights and meals when calculating how much to put aside for your trip to Steward. Then, pick a property that works with your budget, whether that's an economical option or a deluxe retreat.
  3. Determine how many days away: Start by listing all the attractions and activities you want to experience in Steward. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your accommodation and airfare: Once you've settled on your dates and duration, book the right Steward holiday package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.