Search Deals onWestchester Vacation Packages
Westchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Villa Christina
Save 100% on your flight
Price was $751, price is now $511 per person
$511
per person
Oct 8 - Oct 11
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this guesthouse in Chicago. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Griffin Museum of Science and Industry and Obama's House are located nearby.
Property was maintained very well, very clean with some artful style. Staff reaponsed quickly fie any needs or inquiry. Feels like a home. Community is safe and neighbors are nice. Street parking is reletively easy.
Reviewed on Aug 4, 2026
Four Seasons Hotel Chicago
Price was $4,688, price is now $2,724 per person
$2,724
per person
Sep 13 - Sep 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 full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Yes
Reviewed on Aug 3, 2026
Level Chicago – Old Town
Save 100% on your flight
Price was $983, price is now $628 per person
$628
per person
Oct 22 - Oct 25
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.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $1,103, price is now $706 per person
$706
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). 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 $1,197, price is now $793 per person
$793
per person
Sep 14 - Sep 16
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.
Perfect
Reviewed on Aug 4, 2026
Level Chicago - River North
Save 100% on your flight
Price was $941, price is now $651 per person
$651
per person
Sep 10 - Sep 13
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. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
Save 100% on your flight
Price was $832, price is now $579 per person
$579
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicagoland Speedway and Route 66 Raceway are located nearby.
The Emily Hotel
Save 100% on your flight
Price was $1,121, price is now $789 per person
$789
per person
Oct 14 - Oct 17
found 2 days 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.
This was a family trip, so maybe not the right location. There was a LOT of construction in the area. There was no parking for hotel guests, unless you paid over $80 a day for valet only. The space was very modern, but dark. The beds were low to the ground and uncomfortable. Clean, but minimal accommodations. Staff was minimally helpful with questions we had. We won’t be staying here again.
Reviewed on Aug 4, 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.
Sat, Sep 5 - Sun, Sep 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Sat, Sep 5 - Wed, Sep 9
LAX
Los Angeles Intl.
MDW
Midway Intl.
$230 Roundtrip, found 1 day ago
$230
Roundtrip
found 1 day ago
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
Tue, Sep 1 - Fri, Sep 18
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,131 Roundtrip, found 1 day ago
$1,131
Roundtrip
found 1 day ago
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