Search Deals onSleepy Hollow Vacation Packages
Sleepy Hollow Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Save 100% on your flight
Price was $899, price is now $602 per person
$602
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
It’s a beautiful hotel with great location. The staff wasn’t very friendly. It was annoying to pay $6-$13 for a bottle of water. No complimentary microwave. We were told to rent it $34 to warm up our leftovers.
Reviewed on Sep 10, 2026
Level Chicago Fulton Market
Save 100% on your flight
Price was $1,506, price is now $833 per person
$833
per person
Oct 16 - Oct 20
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 Emily Hotel
Save 100% on your flight
Price was $1,763, price is now $1,014 per person
$1,014
per person
Oct 16 - Oct 20
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, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,541, price is now $893 per person
$893
per person
Oct 20 - Oct 24
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.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,682, price is now $1,021 per person
$1,021
per person
Nov 24 - Nov 28
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 breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Talbott, Autograph Collection
Save 100% on your flight
Price was $990, price is now $622 per person
$622
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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.
Stay One Chicago
Save 100% on your flight
Price was $1,459, price is now $957 per person
$957
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, private pools, and 3 restaurants. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Save 100% on your flight
Price was $1,502, price is now $1,007 per person
$1,007
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
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.
Wed, Oct 14 - Sat, Oct 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 4 hours ago
$217
Roundtrip
found 4 hours ago
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 4 hours ago
$217
Roundtrip
found 4 hours ago
Fri, Nov 13 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,163 Roundtrip, found 10 hours ago
$1,163
Roundtrip
found 10 hours ago
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