Sycamore Holidays

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    Save up to €185 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Flight + Hotel Deals in Sycamore

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was €1,182, price is now €723 per person
€723
per person
13 Nov - 19 Nov
found 1 hour ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,320, price is now €1,397 per person
€1,397
per person
13 Nov - 19 Nov
found 1 hour ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on 25 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,734, price is now €1,057 per person
€1,057
per person
13 Nov - 19 Nov
found 1 hour ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,489, price is now €975 per person
€975
per person
13 Nov - 19 Nov
found 1 hour ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on 26 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,287, price is now €852 per person
€852
per person
13 Nov - 19 Nov
found 1 hour ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 Aug 2025

Top hotels in Sycamore

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 €82 per night from 31 Aug to 1 Sept
€82
31 Aug - 1 Sept
includes taxes & fees
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 €94 per night from 31 Aug to 1 Sept
€94
31 Aug - 1 Sept
includes taxes & fees
Best Western Sycamore Inn
Motel 6 Sycamore, IL

Motel 6 Sycamore, IL

2 out of 5
1860 Dekalb Ave, Sycamore, IL
Fully refundableReserve now, pay when you stay
The price is €66 per night from 31 Aug to 1 Sept
€66
31 Aug - 1 Sept
includes taxes & fees
Motel 6 Sycamore, IL
See all 79 properties in Sycamore
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 Sycamore holiday package cost?
You'll find cheap prices from €723 on Expedia for your Sycamore getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your holiday to Sycamore costs.
What are the cheapest months to go to Sycamore?
December, January and February are great times to look for cheap Sycamore holiday packages. Choosing to travel in quieter periods means you'll typically find better prices on hotels and flights.
How many days is enough for Sycamore?
The ideal length for your Sycamore holiday depends on what you'd like to see and do. Usually, a few days to a week will give you enough time to go to all the main sights and explore some hidden gems along the way.
How to find the best Sycamore package deals?
Use Expedia's filters to find some of the best Sycamore 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 break for midweek, or look for Sycamore package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your holiday package as soon as possible.
Is it cheaper to book a Sycamore holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Sycamore holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Sycamore?
If you're planning an impromptu Sycamore adventure, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Sycamore?

  1. Choose your travel dates: The things you want to do in Sycamore and your preferred season will help you decide when to go.
  2. Set a budget: Consider expenses like food, flights and transportation when working out how much to save for your trip to Sycamore. Then, select a property that fits your budget, whether that's a low-cost stay or a swankier getaway.
  3. Work out your trip length: Think about how long you'd like to spend exploring Sycamore. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Sycamore holiday package.

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