Sycamore Vacations from $483
Book a Hotel + Flight or Car together to unlock savings
The Latest Sycamore Vacation Packages
- Hotel Felix River North/Magnificent Mile
Oct 15 - Oct 18Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property8.2/10 - Very Good (2,862 reviews)"There wasn't any coffee machine, or refrigerator or even cups in the room. However, they did have water bottles for $8 each. The fitness center was great! The staff was great! Maybe that was why I was surprised at the lack of convenience items - though I don't know that I've ever been in a room without one."Reviewed July 24, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop MDW - ATL • Nonstop - Hotel Riu Plaza Chicago
Sep 25 - Sep 27Hotel Riu Plaza Chicago + Flight
Downtown Chicago2 nights4.0 star property9.4/10 - Exceptional (4,802 reviews)"All the staff members were extremely helpful and polite. Breakfast was excellent. "Reviewed July 24, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop MDW - ATL • Nonstop - Sable at Navy Pier Chicago, Curio Collection by Hilton
Oct 15 - Oct 18Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (2,617 reviews)"Excellent location. My grandson (3.5 yeas old) and I thoroughly enjoy our daily routine of strolling along the lakeside, having meals, playing games, watching the fireworks and taking in the scenery. The room is clean and the staffs are nice. We spent a wonderful six-day vacation."Reviewed July 24, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop MDW - ATL • Nonstop - Pendry Chicago
Sep 3 - Sep 6Pendry Chicago + Flight
Downtown Chicago3 nights4.5 star property9.2/10 - Wonderful (1,145 reviews)"The first room we were assigned smelled like a cat. I'm severely allergic, so I knew right away (room 2204). The second room (1404) was nice and clean. Unfortunately the noise from Michigan Avenue is pretty much unbearable. It's an old building and no sound proofing has been done to the walls ... even from the 14th floor I could hear sirens all night, cars drag racing, and even gun shots. There are 5-6 elevators on this property, but the first set of 3 services the lobby to floor 22, and..."Reviewed July 23, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - The Talbott, Autograph Collection
Oct 11 - Oct 17The Talbott, Autograph Collection + Flight
Downtown Chicago6 nights4.5 star property9.6/10 - Exceptional (141 reviews)"This hotel is situated in a prime location, making it convenient to get anywhere in Chicago. The staff always greeted guests with bright smiles and provided immediate, friendly assistance with even the smallest requests. The room was very spacious; while there was some noise from neighboring rooms, it wasn't bothersome enough to be a major issue. I would love to stay here again if I visit Chicago in the future."Reviewed July 24, 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 $483 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.