Search Deals onWestchester Vacation Packages
Westchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Wade
Save 100% on your flight
Price was $493, price is now $313 per person
$313
per person
Nov 18 - Nov 21
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 room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,249, price is now $735 per person
$735
per person
Nov 18 - Nov 21
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.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,189, price is now $715 per person
$715
per person
Oct 23 - Oct 26
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 Talbott, Autograph Collection
Save 100% on your flight
Price was $726, price is now $438 per person
$438
per person
Nov 18 - Nov 21
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.
Chicago Lake Shore Hotel
Save 100% on your flight
Price was $599, price is now $369 per person
$369
per person
Nov 26 - Dec 1
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. Popular attractions Soldier Field and Grant Park are located nearby.
The only thing I didn’t like was the stairway, they don’t have elevators. The rooms were clean, bed was comfortable to sleep with, pillows were new restroom was well maintained.
Reviewed on Sep 14, 2026
Arlo Chicago
Save 100% on your flight
Price was $654, price is now $427 per person
$427
per person
Nov 18 - Nov 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Clean
Reviewed on Sep 15, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $618, price is now $407 per person
$407
per person
Nov 18 - Nov 21
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.
Room was clean and quiet. View was amazinggg! Lots of restaurants close by.
Reviewed on Sep 15, 2026
Kimpton Gray Hotel by IHG
Save 100% on your flight
Price was $803, price is now $529 per person
$529
per person
Nov 18 - Nov 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Clean room, nice location
Reviewed on Sep 15, 2026
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.
Wed, Oct 14 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 9 hours ago
$138
Roundtrip
found 9 hours ago
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$215 Roundtrip, found 16 hours ago
$215
Roundtrip
found 16 hours ago
Mon, Oct 5 - Tue, Oct 6
LAX
Los Angeles Intl.
MDW
Midway Intl.
$261 Roundtrip, found 1 day ago
$261
Roundtrip
found 1 day ago
Tue, Nov 10 - Thu, Dec 3
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,178 Roundtrip, just found
$1,178
Roundtrip
just found
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