Search Deals onWestchester Vacation Packages
Westchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk
Price was $1,270, price is now $294 per person
$294
per person
Dec 22 - Dec 24
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.
The Emily Hotel
Save 100% on your flight
Price was $830, price is now $507 per person
$507
per person
Dec 24 - Dec 29
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.
Staff was friendly and the room was clean
Reviewed on Nov 3, 2026
Level Chicago Fulton Market
Price was $639, price is now $403 per person
$403
per person
Jan 5 - Jan 10
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.
Pendry Chicago
Price was $609, price is now $401 per person
$401
per person
Dec 16 - Dec 19
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.
Level Chicago – Old Town
Save 100% on your flight
Price was $718, price is now $480 per person
$480
per person
Jan 25 - Jan 28
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.
Estuvo muy increíble, fue una experiencia maravillosa.Es un lugar precioso me encantó
Reviewed on Nov 1, 2026
Hotel Saint Clair- Magnificent Mile
Save 100% on your flight
Price was $459, price is now $308 per person
$308
per person
Jan 14 - Jan 17
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.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $571, price is now $386 per person
$386
per person
Jan 14 - Jan 17
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.
We thoroughly enjoyed our stay at the Riu Hotel. The location was fantastic. You could go shopping or walk to the lakefront in 5 minutes. The rooms were modern and immaculate. The breakfast was included in our reservation and was great. We were also able to enjoy the rooftop bar with a heater. We would definitely recommend staying here
Reviewed on Nov 4, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $954, price is now $667 per person
$667
per person
Jan 14 - Jan 17
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.
Westchester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Westchester 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.
Fri, Dec 4 - Wed, Dec 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$176 Roundtrip, found 6 hours ago
$176
Roundtrip
found 6 hours ago
Wed, Dec 2 - Fri, Dec 4
LAX
Los Angeles Intl.
MDW
Midway Intl.
$238 Roundtrip, found 9 hours ago
$238
Roundtrip
found 9 hours ago
Mon, Nov 9 - Mon, Feb 1
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,141 Roundtrip, found 2 hours ago
$1,141
Roundtrip
found 2 hours ago
Sun, Nov 8 - Mon, Feb 1
SHA
Hongqiao Intl.
ORD
O'Hare Intl.
$1,570 Roundtrip, found 21 hours ago
$1,570
Roundtrip
found 21 hours ago
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