Sycamore Vacations from $717
Book a Hotel + Flight or Car together to unlock savings
The Latest Sycamore Vacation Packages
- Hotel Riu Plaza Chicago
Sep 11 - Sep 14Hotel Riu Plaza Chicago + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (4,843 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Four Seasons Hotel Chicago
Oct 13 - Oct 18Four Seasons Hotel Chicago + Flight
Downtown Chicago5 nights5.0 star property9.4/10 - Exceptional (1,002 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop - Level Chicago – Old Town
Sep 13 - Sep 16Level Chicago – Old Town + Flight
Downtown Chicago3 nights4.0 star property9.0/10 - Wonderful (509 reviews)"this is no a hotel and the amenities are bare bones. No maid service, the TV was worthless with endless buffering to make it unwatchable, the shower head was broken, etc. On the good side, it's a great location, beautiful views, nice vibe around the property, large unit with two beds, and great gym area."Reviewed July 27, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Sable at Navy Pier Chicago, Curio Collection by Hilton
Aug 28 - Aug 31Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (2,631 reviews)"One of the best hotel I’ve ever stayed in!!"Reviewed July 27, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago - River North
Sep 16 - Sep 19Level Chicago - River North + Flight
Downtown Chicago3 nights4.0 star property9.2/10 - Wonderful (1,040 reviews)"We had such a great stay! Only complaint was one of the blinds would not shut in one of the bedrooms, but we understood it was probably not fixable in the 2 days we were there. We were also upgraded to a better room upon arrival! Overall 10/10!"Reviewed July 23, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop
Discover the most popular places to visit in Sycamore
Sycamore Hotel Deals
Country Inn & Suites by Radisson, Sycamore, IL
Country Inn & Suites by Radisson, Sycamore, IL
Comfort Inn DeKalb - University Area
Comfort Inn DeKalb - University Area
Frequently Asked Questions
How much does a Sycamore vacation package cost?
You'll find cheap prices from $717 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 vacation to Sycamore costs.
What are the cheapest months to go to Sycamore?
You're likely to find reduced prices and better availability in July, November and December. Take a look at our cheap Sycamore vacation packages and you could get some excellent off-season deals.
How many days is enough for Sycamore?
Generally, a handful of days is enough to visit the top attractions during your Sycamore vacation. However, if you want to have more time to kick back or go on day tours, think about extending your itinerary.
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 vacation package as soon as possible.
Is it cheaper to book a Sycamore vacation as a package?
Expedia vacation 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 vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Sycamore vacation packages?
If you're anything like us, you love traveling the world but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Sycamore trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.