Sycamore Vacations from $396
Book a Hotel + Flight or Car together to unlock savings
The Latest Sycamore Vacation Packages
- Hotel Felix River North/Magnificent Mile
Oct 4 - Oct 7Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property8.2/10 - Very Good (2,878 reviews)"GreatGreat quite wonderful"Reviewed July 30, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Hotel Riu Plaza Chicago
Oct 4 - Oct 7Hotel Riu Plaza Chicago + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (4,873 reviews)"I had an amazing experience. The room was very clean with a comfy bed. The staff, especially Alan, was very helpful. He was patient and supportive."Reviewed July 30, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Pendry Chicago
Oct 4 - Oct 7Pendry Chicago + Flight
Downtown Chicago3 nights4.5 star property9.2/10 - Wonderful (1,152 reviews)"The property is one of the coolest places in Chicago. Conveniently located to the Magnificent Mile, Millennial Park, and the Theater District."Reviewed July 28, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Sable at Navy Pier Chicago, Curio Collection by Hilton
Oct 4 - Oct 7Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (2,620 reviews)"Beautiful hotel with fabulous views of the lake and skyline. Loved the layout of the room, with a little nook looking out on the lake/people. Generally, staff were very helpful. Our room was not attended to at all on one day of our 3 day stay. Housekeeping did bring supplies on that day when requested. Walkable to Streeterville and Magnificent Mile. Lots of crowds on Navy Pier on summer weekend, but room was not overly noisy. Overall, a great stay!"Reviewed July 30, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Hotel Saint Clair- Magnificent Mile
Sep 11 - Sep 14Hotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property8.4/10 - Very Good (2,072 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • 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 $396 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.