Search Deals onSleepy Hollow Vacation Packages
Sleepy Hollow Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
Save 100% on your flight
Price was $452, price is now $295 per person
$295
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
2 adults staying in a room with double beds. Room wasn't that big. Didn't have a closet, buttons on the safe didn't work properly, there was no fridge in the room and there was no cleaning services provided without paying more. It was fine for us as we were only there to sleep, but would be pretty crammed if in a group of 3-4 people.
Location was great. Easily accessible by transit and close to the Bean, Boat tour and Art Institute.
Overall, found it was a good value considering price point of other comparable hotels, but don't expect any frills while staying.
Reviewed on Oct 26, 2026
Sheraton Grand Chicago Riverwalk
Price was $1,547, price is now $451 per person
$451
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market
Save 100% on your flight
Price was $690, price is now $406 per person
$406
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The stay was everything I love the view and peaceful. Thank you
Reviewed on Oct 26, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $786, price is now $463 per person
$463
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Peninsula Chicago
Save 100% on your flight
Price was $1,907, price is now $1,179 per person
$1,179
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Price was $704, price is now $446 per person
$446
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Super clean. Super views. Super amenities. Will stay again.
Reviewed on Oct 26, 2026
Pendry Chicago
Price was $575, price is now $374 per person
$374
per person
Dec 28 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $641, price is now $425 per person
$425
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Sleepy Hollow Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Sleepy Hollow Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Dec 7 - Sat, Dec 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$150 Roundtrip, found 2 hours ago
$150
Roundtrip
found 2 hours ago
Sat, Dec 26 - Wed, Jan 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$224 Roundtrip, found 2 days ago
$224
Roundtrip
found 2 days ago
Tue, Nov 10 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,156 Roundtrip, found 5 hours ago
$1,156
Roundtrip
found 5 hours ago
Sun, Nov 8 - Mon, Feb 1
SHA
Hongqiao Intl.
ORD
O'Hare Intl.
$1,773 Roundtrip, found 2 hours ago
$1,773
Roundtrip
found 2 hours ago
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